Name: 5428-09-1|2-Allylisoindoline-1,3-dione|95%
Brand: Ambeed
SKU: A162523
Price: 7.0 USD
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1
[ 85-44-9 ]
[ 107-11-9 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	In water; ethyl acetate; N,N-dimethyl-formamide	A Step A Step A Preparation of N-allylphthalimide (1-1) A 500 mL round-bottom flask was charged with phthalic anhydride (22.2 g, 150 mmol) and anhydrous DMF (150 mL) and stirred at room temperature for 5 min to dissolve the phthalic anhydride. To the solution was slowly added allylamine (11.26 mL, 150 mmol) followed by 20 g of 3A molecular sieves. The resulting mixture was stirred at room temperature 10 minutes and then heated under nitrogen at 80° C. for 16 hrs. The reaction mixture was cooled to room temperature and filtered. To the mother liquor was added 300 mL of EtOAc and 300 mL of brine solution. The organic layer was separated, washed twice with 300 mL of water, and dried over MgSO4. The drying agent was removed by filtration and the mother liquor concentrated. The resulting solid was recrystallized from CH2Cl2/hexane to yield 27.75 g (98% yield) of N-allylphthalimide (1-1).
97%	With molecular sieve In N,N-dimethyl-formamide
95%	With triethylamine In toluene for 3.5h; Heating;

95%	With niobium(V) oxide In hexane for 30h; Inert atmosphere; Reflux;
91%	With acetic acid at 150℃; for 2h; Microwave irradiation;
86%	Stage #1: phthalic anhydride; 1-amino-2-propene In toluene at 20℃; for 16h; Stage #2: In toluene for 14h; Heating;
85%	With acetic acid at 20 - 110℃; for 4h; Reflux; Inert atmosphere;	1.1 Embodiment 1 Under nitrogen atmosphere, in 250 ml of adding three-necked bottle 14.8g (0.1mol) phthalic anhydride and 150 ml glacial acetic acid, to be completely dissolved after adding dropwise under stirring 5.7g (0.1mol) ene propyl amine, the reaction at room temperature 1h, then heating to 110 °C reaction refluxing 3h. Stop reaction, to be cooled to the room temperature, is poured into 300 ml water, immediately with a white precipitate out, filtered, the filter cake three times washing with water, drying to obtain white powdery product (A1) 15.8g, the yield is 85%.
75%	With acetic acid for 2h; Heating;
75%	With acetic acid for 2h; Reflux;	Synthesis of of N-allyl-phthalimide 4 To a solution of allyl amine (5.70 g, 100 mmol) in acetic acid (30 ml), phthalic anhydride (14.8 g, 100 mmol) was added with stirring. The mixture was refluxed for 2h and then was poured into water (300 ml). The precipitates were formed and filtered. Further recrystallization from ethyl acetate afforded N-allylphthalimide as the colorless crystals; yield: 75%.
	With acetic acid
	With ethanol
	With water
	In N,N-dimethyl-formamide at 100℃;
	With triethylamine In toluene for 36h; Inert atmosphere; Dean-Stark; Reflux;
	With triethylamine In toluene Reflux;
	With acetic acid at 100 - 130℃; for 6h; Inert atmosphere;	1 Equipped with a stirrer, a reflux condenser and a thermometer three 500ml glass flask, 87g of phthalic anhydride and 300ml glacial acetic acid, was added to start stirring and 60g of allylamine, 2h after passed through N2Heating temperature, and 100 Cthe C ~ 130.Cthe C maintained 4h, then cooled to room temperature, 100ml of water was added, the precipitated solid was a large number of suction filtration to give N- allylbenzene imide crystal 101g, a yield of 98%,
	With triethylamine In toluene Reflux; Inert atmosphere; Schlenk technique;
	With triethylamine In toluene at 110℃; for 4h; Inert atmosphere; Dean-Stark;

Reference： [1]Current Patent Assignee: MERCK & CO INC - US6262268, 2001, B1
[2]Palucki, Michael; Hughes, David L; Yasuda, Nobuyoshi; Yang, Chunhua; Reider, Paul J [Tetrahedron Letters, 2001, vol. 42, # 39, p. 6811 - 6814]
[3]Varala, Ravi; Adapa, Srinivas R. [Synthetic Communications, 2006, vol. 36, # 24, p. 3743 - 3747]
[4]Ali, Md. Ayub; Siddiki, S. M. A. Hakim; Kon, Kenichi; Hasegawa, Junya; Shimizu, Kenichi [Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14256 - 14260]
[5]Location in patent: experimental part Prediger, Patricia; Barbosa, Lais Ferreira; Genisson, Yves; Correia, Carlos Roque Duarte [Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7737 - 7749]
[6]Duda-Johner, Seraina; Daiß, Jürgen O.; Mohr, Klaus; Tacke, Reinhold [Journal of Organometallic Chemistry, 2003, vol. 686, # 1-2, p. 75 - 83]
[7]Current Patent Assignee: NANCHANG UNIVERSITY - CN105669738, 2016, A Location in patent: Paragraph 0023; 0024
[8]Abulikemu, Abudurexiti; Halász, Gábor; Csámpai, Antal; Gömöry, Ágnes; Rábai, József [Journal of Fluorine Chemistry, 2004, vol. 125, # 7, p. 1143 - 1146]
[9]Kakaei, Saeed; Chen, Ning; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 1, p. 302 - 309]
[10]Carrara; Mori [Gazzetta Chimica Italiana, 1943, vol. 73, p. 113,115] Dominikiewicz [Archiwum Chemji i Farmacji, 1937, vol. 3, p. 141,149][Chemisches Zentralblatt, 1937, vol. 108, # II, p. 3744] Wanag [Latvijas universitates raksti. Kimijas fakultates serija, 1938, vol. 4, p. 405,415, 420]
[11]Carrara; Mori [Gazzetta Chimica Italiana, 1943, vol. 73, p. 113,115] Dominikiewicz [Archiwum Chemji i Farmacji, 1937, vol. 3, p. 141,149][Chemisches Zentralblatt, 1937, vol. 108, # II, p. 3744] Wanag [Latvijas universitates raksti. Kimijas fakultates serija, 1938, vol. 4, p. 405,415, 420]
[12]Carrara; Mori [Gazzetta Chimica Italiana, 1943, vol. 73, p. 113,115] Dominikiewicz [Archiwum Chemji i Farmacji, 1937, vol. 3, p. 141,149][Chemisches Zentralblatt, 1937, vol. 108, # II, p. 3744] Wanag [Latvijas universitates raksti. Kimijas fakultates serija, 1938, vol. 4, p. 405,415, 420]
[13]Thayumanavan, Rajeswari; Tanaka, Fujie; Barbas III, Carlos F. [Organic Letters, 2004, vol. 6, # 20, p. 3541 - 3544]
[14]Maity, Arnab Kumar; Roy, Sujit [Advanced Synthesis and Catalysis, 2014, vol. 356, # 11-12, p. 2627 - 2642]
[15]Chen, Caiyou; Jin, Shicheng; Zhang, Zhefan; Wei, Biao; Wang, Heng; Zhang, Kai; Lv, Hui; Dong, Xiu-Qin; Zhang, Xumu [Journal of the American Chemical Society, 2016, vol. 138, # 29, p. 9017 - 9020]
[16]Current Patent Assignee: Nanchang University; Liu, Feng; Wang, Xiulong; Qi, Haixia - CN102276639, 2016, B Location in patent: Paragraph 0033; 0035
[17][Journal of the American Chemical Society, 2017, vol. 139, # 11, p. 4230 - 4230]
[18]Liu, Jiaan; Li, Yanfeng; Deol, Kirandeep K.; Strieter, Eric R. [Organic Letters, 2019, vol. 21, # 17, p. 6790 - 6794]

2
[ 5428-09-1 ]
2-(2,3-dichloropropyl) isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; copper dichloride In acetonitrile at 20℃; for 72h; Irradiation;	1 Example 1 Add 1a (0.2mmol, 37.4mg) to the test tube at one time,CuCl2 (0.04mmol, 5.4mg), acetonitrile MeCN (0.5mL),HCl (0.5 mmol, 41 μL).Then the system was irradiated with 38W white LED under the room temperature in the air and stirred for 72 hours,The reaction system was quenched with saturated sodium sulfite solution, extracted three times with ethyl acetate, and the organic layers were combined and dried over anhydrous sodium sulfate.Use a rotary evaporator to remove the solvent, silica gel adsorption, the product 2a can be obtained by simple column chromatography, the yield is 85%.The main test data of the prepared product is as follows. It can be known from the analysis that the actual synthesized product is consistent with the theoretical analysis.
85%	With hydrogenchloride; copper dichloride In water; acetonitrile at 20℃; for 72h; Schlenk technique; Irradiation;
	With chloroform; chlorine

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN111253254, 2020, A Location in patent: Paragraph 0043-0046
[2]Li, Jingjing; Lian, Pengcheng; Long, Wenhao; Wan, Xiaobing; Zheng, Yonggao [Angewandte Chemie - International Edition, 2020, vol. 59, # 52, p. 23603 - 23608][Angewandte Chemie, 2020, vol. 132, # 52, p. 23809 - 23814,6]
[3]Neumann [Chemische Berichte, 1890, vol. 23, p. 995]

3
[ 1074-82-4 ]
[ 106-95-6 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	In N,N-dimethyl-formamide at 50℃; for 12h;
95%	In N,N-dimethyl-formamide at 55℃; for 17h; Inert atmosphere;	To a 100 ml two-necked round bottom flask, 5.08 g phthalimide potassium salt (27.4 mmol) and 30 ml allylbromine (26.6 mmol) were dissolved in 40 ml DMF under the nitrogen atmosphere. The mixture was stirred for half an hour at 55 °C for 17 h, then 200 ml H2O was added and the mixture was extracted with CH2Cl2 (80 ml × 3). The combined organic phase was dried over anhydrous Mg2SO4. After the removal of solvent under reduced pressure, the crude product was purified by column chromatography on silica gel with CH2Cl2 as the eluent, the collected pale yellow oil was determined to be the desired product 2-allylisoindoline-1,3-dione (4.87 g, 95% yield). 1H NMR (400 MHz, CDCl3): δ 7.90 (m, 2H), 7.76 (m. 2H), 5.93 (m, 1H), 5.26 (m, 2H), 4.34 (d, J = 8.0 Hz, 2H). 13C NMR (101 MHz, CDCl3): δ 167.95, 134.04, 132.26, 131.67, 123.37, 117.84, 40.14.
92%	With cetyltributylphosphonium bromide In toluene at 100℃; for 18h;

89%	With tetrabutylammomium bromide; silica gel for 0.0666667h; microwave irradiation;
82%	With 18-crown-6 ether In toluene
80.2%	In N,N-dimethyl-formamide at 50℃;
80%	With tetrabutylammomium bromide In N,N-dimethyl-formamide at 20℃;
72%	With Aliquat 336 In N,N-dimethyl-formamide at 20℃;
72%	With Aliquat 336 In N,N-dimethyl-formamide at 20℃;
68%	With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;
68%	With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 20h;
65%	In acetonitrile at 150℃; for 8h;
60%	With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide for 20h; Ambient temperature;
57%	In N,N-dimethyl-formamide at 70℃; for 16h;	100.1 To a solution of phtalamide potassium salt (6 g, 32.4 mmol) in DMF (40 mL), was added allyl bromide (2.78 mL, 32.4 mmol). The solution was heated to 7O0C and stirred for 16h. The DMF was removed by rotary evaporation and aqueous extraction was performed with ethyl acetate and water and the organic layer was separated, dried with NaSO4 and concentrated. The residue was purified by silica gel column chromatography with a gradient of ethyl acetate (20-80%) in hexanes to afford 241 (3.4 g, 57%) as a white solid.(DMSO-crø) δ(ppm): 7.89 - 7.80 (m, 4H)1 5.90 - 5.80 (m, 1H), 5.12 (t, J=1.6 Hz, 1H), 5.10 -5.06 (m, 1 H), 4.16 (dt, J=5.1 , 1.8 Hz, 2H)
28%	With 1-decyl-3-phenylmethyl-1H-imidazolium bromide; water at 25℃; for 2h;
	With ethanol
	at 150℃;
	In N,N-dimethyl-formamide at 70℃;
	In N,N-dimethyl-formamide at 80℃; for 16h;

Reference： [1]Location in patent: experimental part Mosley, Cara A.; Myers, Scott J.; Murray, Ernest E.; Santangelo, Rose; Tahirovic, Yesim A.; Kurtkaya, Natalie; Mullasseril, Praseeda; Yuan, Hongjie; Lyuboslavsky, Polina; Le, Phuong; Wilson, Lawrence J.; Yepes, Manuel; Dingledine, Ray; Traynelis, Stephen F.; Liotta, Dennis C. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 17, p. 6463 - 6480]
[2]Wu, Huarui; Zheng, Chaoyue; Chen, Naiwu; Zhu, Jie; Gao, Deqing [Tetrahedron Letters, 2017, vol. 58, # 16, p. 1576 - 1578]
[3]Anelli, Pier Lucio; Montanari, Fernando; Pollak, Vladimir; Quici, Silvio [Gazzetta Chimica Italiana, 1986, vol. 116, # 3, p. 127 - 132]
[4]Hekmatshoar; Heravi; Baghernejad; Asadolah [Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 8, p. 1611 - 1614]
[5]Carruthers, Nicholas I.; Spitler, James M.; Wong, Shing-Chun; Blythin, David J.; Chen, Xiao; Shue, Ho-Jane; She, Hoyan S.; Lee, Joe F.; Rizzo, Charles; Ting, Pauline C.; West Jr., Robert E. [Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 21, p. 3059 - 3064]
[6]Heyes; Niculescu-Duvaz; Cooper; Springer [Journal of Medicinal Chemistry, 2002, vol. 45, # 1, p. 99 - 114]
[7]Zhang, Xiaowei; Cao, Bonan; Yu, Shichao; Zhang, Xumu [Angewandte Chemie - International Edition, 2010, vol. 49, # 24, p. 4047 - 4050]
[8]Koehling, Petra; Schmidt, Axel M.; Eilbracht, Peter [Organic Letters, 2003, vol. 5, # 18, p. 3213 - 3216]
[9]Schmidt, Axel M.; Eilbracht, Peter [Organic and Biomolecular Chemistry, 2005, vol. 3, # 12, p. 2333 - 2343]
[10]De-Nanteuil, Florian; Waser, Jerome [Angewandte Chemie - International Edition, 2013, vol. 52, # 34, p. 9009 - 9013][Angew. Chem., 2013, vol. 125, # 34, p. 9179 - 9183,5]
[11]Waser, Jerome; Perrotta, Daniele; Racine, Sophie; Vuilleumier, Jeremy; De Nanteuil, Florian [Organic Letters, 2015, vol. 17, # 4, p. 1030 - 1033]
[12]Chou, Ta-Shue; Tsai, Chung-Ying [Journal of the Chinese Chemical Society, 1993, vol. 40, # 6, p. 581 - 586]
[13]Stojanovic, Aleksandar; Renaud, Philippe; Schenk, Kurt [Helvetica Chimica Acta, 1998, vol. 81, # 2, p. 268 - 284]
[14]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - WO2006/102760, 2006, A1 Location in patent: Page/Page column 147; 148
[15]Location in patent: experimental part Asano, Keisuke; Matsubara, Seijiro [Heterocycles, 2010, vol. 80, # 2, p. 989 - 1002]
[16]Baker et al. [Journal of Organic Chemistry, 1952, vol. 17, p. 149,153]
[17]Neumann [Chemische Berichte, 1890, vol. 23, p. 995]
[18]Breslin, Michael J.; Duggan, Mark E.; Halczenko, Wasyl; Hartman, George D.; Duong, Le T.; Fernandez-Metzler, Carmen; Gentile, Michael A.; Kimmel, Donald B.; Leu, Chih-Tai; Merkle, Kara; Prueksaritanont, Thomayant; Rodan, Gideon A.; Rodan, Sevgi B.; Hutchinson, John H. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4515 - 4518]
[19]Panek, Dawid; Wiȩckowska, Anna; Pasieka, Anna; Godyń, Justyna; Jończyk, Jakub; Bajda, Marek; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara [Molecules, 2018, vol. 23, # 2]

4
[ 136918-14-4 ]
[ 107-18-6 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With bis(3-(perfluoro-t-butyloxy)propyl)diazodicarboxylate; bis-phenyl-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phosphine In tetrahydrofuran at 20℃; Inert atmosphere;
79%	With PhP(C₆H₄-p-(CH₂)2C₆F₁₃)2; bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)diazo dicarboxylate In tetrahydrofuran
68%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 17h;

67%	With 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) bromide trihydrate; tetrabutylammonium acetate; zinc In N,N-dimethyl acetamide at 80℃; for 66h; Inert atmosphere;
33%	With Ni{α,α'-bis(diphenylphosphino)-o-xylene}2 In neat (no solvent) at 80℃; for 18h; Schlenk technique; Inert atmosphere; Green chemistry;

Reference： [1]Chu, Qianli; Henry, Christopher; Curran, Dennis P. [Organic Letters, 2008, vol. 10, # 12, p. 2453 - 2456]
[2]Dandapani, Sivaraman; Curran, Dennis P. [Tetrahedron, 2002, vol. 58, # 20, p. 3855 - 3864]
[3]Hitchings, Gregory J.; Helliwell, Madeleine; Vernon, John M. [Journal of the Chemical Society. Perkin transactions I, 1990, # 1, p. 83 - 87]
[4]Sweeney, Joseph B.; Ball, Anthony K.; Lawrence, Philippa A.; Sinclair, Mackenzie C.; Smith, Luke J. [Angewandte Chemie - International Edition, 2018, vol. 57, # 32, p. 10202 - 10206][Angew. Chem., 2018, vol. 130, p. 10359 - 10363,5]
[5]Azizi, Mohamed Salah; Edder, Youssef; Karim, Abdallah; Sauthier, Mathieu [European Journal of Organic Chemistry, 2016, vol. 2016, # 22, p. 3796 - 3803]

5
[ 136918-14-4 ]
[ 106-95-6 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	In N,N-dimethyl-formamide for 3h;	7-1 Example 7-1: Preparation of 2-allylisoindoline-1 ,3-dione II To a solution of Phtalimide (15.0 g, 102 mmol) in DMF (100 mL) was added Allylbromide (12.3 g, 8.82 mL, 102 mmol). After 3 h stirring at room temperature Et02(300 mL) was added to the reaction and washed with sat. aq. NaCI solution (3 x 75 mL). The solvent was removed under reduced pressure affording the title compound (19.0 g, 101 mmol, 99.0 %) as a colourless solid, which was used for the next step without further purification. Rf: 0.43 (Cyclohexane/EtOAc = 85:15)1H NMR (300 MHz, CDCI3) 6 = 4.29 (dt, J= 5.7, 1.5 Hz, 2 H), 5.15-5.31 (m, 2 H),5.79 - 5.97 (m, 1 H), 7.68 - 7.76 (m, 2 H), 7.80 - 7.89 (m, 2 H).13C-NMR (75.5 MHz, CDCI3) 6 = 40.03, 117.72, 123.27, 131.50, 132.10, 133.94,167.88.
99%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	7-1 Example 7-1 Preparation of 2-allylisoindoline-1,3-dione 11 Example 7-1 Preparation of 2-allylisoindoline-1,3-dione 11 To a solution of Phtalimide (15.0 g, 102 mmol) in DMF (100 mL) was added Allylbromide (12.3 g, 8.82 mL, 102 mmol). After 3 h stirring at room temperature EtO2 (300 mL) was added to the reaction and washed with sat. aq. NaCl solution (3 * 75 mL). The solvent was removed under reduced pressure affording the title compound (19.0 g, 101 mmol, 99.0 %) as a colourless solid, which was used for the next step without further purification. Rf: 0.43 (Cyclohexane/EtOAc = 85:15) 1H NMR (300 MHz, CDCl3) δ = 4.29 (dt, J = 5.7, 1.5 Hz, 2 H), 5.15 - 5.31 (m, 2 H), 5.79 - 5.97 (m, 1 H), 7.68 - 7.76 (m, 2 H), 7.80 - 7.89 (m, 2 H). 13C-NMR (75.5 MHz, CDCl3) δ = 40.03, 117.72, 123.27, 131.50, 132.10, 133.94, 167.88.
99%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;

95%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;
95%	With potassium carbonate In neat (no solvent) at 60 - 65℃; for 0.0666667h; Microwave irradiation; Green chemistry;	a.5 4.3. General procedure for preparation of N-alkylphthalimide (7a-e, 8a, 8b) General procedure: A mixture of phthalimide (4.8 mmol, 0.70 g), alkyl halide(6.0 mmol), 4a or 4b (0.3 mmol, 3 mol%) and potassiumcarbonate (18.8 mmol, 2.6 g) was heated in a commercialmicrowave oven in an open Erlenmeyer flask at 60 8C-65 8Cfor the required time (as shown in Table 3) according to a50:10-s heating: cooling cycle, each at an 80% power level.The completion of the reaction was monitored using TLC.After cooling to r.t., the reaction mixture was extracted withmethylene chloride (2 25 mL). Then the extracts weredried over anhydrous Na2SO4, filtered, and the solvent wasevaporated to dryness to give the crude product. Solids werepurified through recrystallization in absolute EtOH, and liquids were purified over a silica gel column using hexane:EtOAc (96:4) as the eluent. The successful formation of theproducts was confirmed by 1H NMR, 13C NMR and FT-IRspectra.
91%	With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 18h;
90%	With Aliquat 336; potassium carbonate In N,N-dimethyl-formamide for 20h; Ambient temperature;
89%	With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 18h;
87%	With potassium carbonate at 20℃; for 16h;
83.7%	Stage #1: phthalimide With potassium hydroxide In ethanol at 20℃; for 2h; Stage #2: allyl bromide In ethanol for 72h; Reflux;	4.3.1 2-(Prop-2-yn-1-yl)isoindolin-1,3-dione (2) General procedure: Compound 1 (1.71g, 11.6mmol) was suspended in EtOH (20mL) and KOH (0.650g, 11.6mmol) was added. The mixture was stirred at room temperature for 2h, and evaporated to remove EtOH. The residue was dissolved in anhydrous DMF (15mL) and propargyl bromide (1.10mL, 12.8mmol) was added. The mixture was stirred at reflux for 72h. The resulting solution was cooled, diluted with EtOAc and partitioned with saturated NaHCO3. The organic phase was washed with water and brine. The solvent was removed by rotary evaporation. The residue was treated with MeOH, and the suspension was filtered to provide compound 2 (1.25g, 6.75mmol, 58.1%) as a white solid.
81%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 5h; Inert atmosphere; Schlenk technique;
62%	With dimethyl sulfoxide; potassium hydroxide at 70℃; for 12h;
60%	With potassium carbonate In acetonitrile at 90℃; for 13h;
50%	With potassium carbonate In acetonitrile at 24 - 95℃; for 6h; Inert atmosphere;
45%	Stage #1: phthalimide With sodium hydride In tetrahydrofuran Stage #2: allyl bromide In tetrahydrofuran
	With potassium hydroxide; 18-crown-6 ether; potassium carbonate 1.) dioxane, RT, 10 min, 2.) dioxane, reflux, 18 h; Yield given. Multistep reaction;
	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given;
	With potassium hexamethylsilazane In N,N-dimethyl-formamide at 0 - 20℃;
	In N,N-dimethyl-formamide at 20℃; for 3h;	7-1 Preparation of 2-allylisoindoline-1,3-dione I1 To a solution of Phtalimide (15.0 g, 102 mmol) in DMF (100 mL) was added Allylbromide (12.3 g, 8.82 mL, 102 mmol). After 3 h stirring at room temperature EtO2 (300 mL) was added to the reaction and washed with sat. aq. NaCl solution (3×75 mL). The solvent was removed under reduced pressure affording the title compound (19.0 g, 101 mmol, 99.0%) as a colourless solid, which was used for the next step without further purification. (0395) Rf: 0.43 (Cyclohexane/EtOAc=85:15) (0396) 1H NMR (300 MHz, CDCl3) δ=4.29 (dt, J=5.7, 1.5 Hz, 2H), 5.15-5.31 (m, 2H), 5.79-5.97 (m, 1H), 7.68-7.76 (m, 2H), 7.80-7.89 (m, 2H). (0397) 13C-NMR (75.5 MHz, CDCl3) δ=40.03, 117.72, 123.27, 131.50, 132.10, 133.94, 167.88
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;

Reference： [1]Current Patent Assignee: MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFT E.V. - WO2015/110271, 2015, A1 Location in patent: Page/Page column 108; 109; 110
[2]Current Patent Assignee: MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFT E.V. - EP2899192, 2015, A1 Location in patent: Paragraph 0191; 0192
[3]Zhang, Yang; Torker, Sebastian; Sigrist, Michel; Bregović, Nikola; Dydio, Paweł [Journal of the American Chemical Society, 2020, vol. 142, # 42, p. 18251 - 18265]
[4]Xiong, Tao; Li, Yan; Mao, Lujia; Zhang, Qian [Chemical Communications, 2012, vol. 48, # 16, p. 2246 - 2248]
[5]Dogra, Shallu; Sharma, Madan L.; Singh, Jasvinder [Comptes Rendus Chimie, 2015, vol. 18, # 9, p. 945 - 953]
[6]Ding, Guangni; Lu, Bin; Li, Yuyuan; Wan, Jun; Zhang, Zhaoguo; Xie, Xiaomin [Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 1013 - 1021]
[7]Delogu, Giovanna; Faedda, Giovanni; Gladiali, Serafino [Journal of Organometallic Chemistry, 1984, vol. 268, # 2, p. 167 - 174]
[8]Bai, Ya; Shi, Lingling; Zheng, Lianyou; Ning, Shulin; Che, Xin; Zhang, Zhuoqi; Xiang, Jinbao [Organic Letters, 2021, vol. 23, # 6, p. 2298 - 2302]
[9]Calamante, Massimo; Dei, Filippo; Maramai, Samuele; Migliorini, Francesca; Petricci, Elena [ChemCatChem, 2021, vol. 13, # 12, p. 2794 - 2806]
[10]Aldrich, Courtney; Brody, Scott; Cushman, Mark; Fan, Bing-Zhi; Hiasa, Hiroshi; Liang, Jian-Hua; Lv, Wei; Yang, Zhao-Yong [European Journal of Medicinal Chemistry, 2020, vol. 193]
[11]Wu, Xiaoyu; Ding, Guangni; Yang, Liqun; Lu, Wenkui; Li, Wanfang; Zhang, Zhaoguo; Xie, Xiaomin [Organic Letters, 2018, vol. 20, # 18, p. 5610 - 5613]
[12]Kannadasan, Sathananthan; Novanna, Motakatla; Shanmugam, Ponnusamy; Smile, Suresh Snoxma [RSC Advances, 2022, vol. 12, # 3, p. 1834 - 1839]
[13]Ning, Xiao-Shan; Wang, Mei-Mei; Yao, Chuan-Zhi; Chen, Xian-Min; Kang, Yan-Biao [Organic Letters, 2016, vol. 18, # 11, p. 2700 - 2703]
[14]Ma, Xiaoshen; Dang, Hester; Rose, John A.; Rablen, Paul; Herzon, Seth B. [Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5998 - 6007]
[15]Ohmura, Naoya; Nakamura, Asami; Hamasaki, Akiyuki; Tokunaga, Makoto [European Journal of Organic Chemistry, 2008, # 30, p. 5042 - 5045]
[16]Lohray; Sekar Reddy; Bhushan, Vidya [Tetrahedron Asymmetry, 1996, vol. 7, # 8, p. 2411 - 2416]
[17]Fichert, Thomas; Massing, Ulrich [Tetrahedron Letters, 1998, vol. 39, # 28, p. 5017 - 5018]
[18]Neugnot, Benjamin; Cintrat, Jean-Christophe; Rousseau, Bernard [Tetrahedron, 2004, vol. 60, # 16, p. 3575 - 3579]
[19]Current Patent Assignee: MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFT E.V. - US2017/2003, 2017, A1 Location in patent: Paragraph 0394-0397
[20]Guo, Quanping; Wang, Mengran; Wang, Yanfang; Xu, Zhaoqing; Wang, Rui [Chemical Communications, 2017, vol. 53, # 91, p. 12317 - 12320]
[21]Mao, Lujia; Bertermann, Rüdiger; Rachor, Simon G.; Szabó, Kálmán J.; Marder, Todd B. [Organic Letters, 2017, vol. 19, # 24, p. 6590 - 6593]
[22]Pomplun, Sebastian; Sippel, Claudia; Hähle, Andreas; Tay, Donald; Shima, Kensuke; Klages, Alina; Ünal, Can Murat; Rieß, Benedikt; Toh, Hui Ting; Hansen, Guido; Yoon, Ho Sup; Bracher, Andreas; Preiser, Peter; Rupp, Jan; Steinert, Michael; Hausch, Felix [Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3660 - 3673]

6
[ 67-56-1 ]
[ 5428-09-1 ]
[ 23244-58-8 ]

Yield	Reaction Conditions	Operation in experiment
6%	With sodium hydroxide; ozone at -78℃; for 3h;
6%	With sodium hydroxide; ozone In dichloromethane at -78℃; for 2.5h;

Reference： [1]Jumnah, Roshan; Williams, Jonathan M. J.; Williams, Andrew C. [Tetrahedron Letters, 1993, vol. 34, # 41, p. 6619 - 6622]
[2]Bower, Justin F.; Jumnah, Roshan; Williams, Andrew C.; Williams, Jonathan M. J. [Journal of the Chemical Society. Perkin transactions I, 1997, # 9, p. 1411 - 1420]

7
[ 5428-09-1 ]
[ 106-41-2 ]
[ 83680-96-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 100℃; for 18h;
	With triethylamine In N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere;	11 Synthesis of cinnamyl amines (117, 119); [00337] To a stirred mixture of phthalimide potassium salt (20 g, 108 mmol) and tetrabutylammonium bromide (1.04 g, 3.24 mmol, 0.03 equiv) in anhydrous DMF (75 mL) was added allyl chloride (8.84 mL, 108 mmol) at room temperature, and the mixture was stirred at room temperature for 22 h, resulting in a light-yellow suspension. The reaction was quenched by adding cold H20 (150 mL), and the mixture was stirred for 10 min (an ice bath was applied during this time to aid the precipitation). The resulting white suspension was filtered off, washed with H20 (3x50 mL), and air-dried to give N-allylphthalimide (8.5 g, 42% yield) as white solid.[00338] Aryl bromide (10 mmol), N-allylphthalimide (1.93 g, 10.3 mol, 1.03 equiv) and triethylamine (2.78 mL, 20 mmol, 2 equiv) were placed in a 50 mL three-necked round bottom flask, palladium acetate (23 mg, 0.1 mmol, 0.01 equiv) and tri-O-tolylphosphine (61 mg, 0.2 mmol, 0.02 equiv) were added to the flask under the flash of argon, and the whole mixture was heated at 100 (bath temperature) unde r argon and with stirring for 16 h. After the reaction mixture was cooled to ambient temperature, DCM (50 mL) and H20 (50 mL) were added, and stirred at room temperature for 10 min. The DCM layer was separated, and the aqueous layer was extracted with DCM (2x50 mL). The combined DCM layers were washed with H20 (50 mL) and brine (50 mL), and dried. The solvent was evaporated by a rotary evaporator to dryness, and the crude product was purified by flash column chromatography (eluting with 30-80% EtOAc in hexane) to afford N-cinnamyl phthalimide (116 or 118).[00339] N-cinnamyl phthalimide (3 mmol) was mixed with 65% hydrazine hydrate (6 mmol, 2 equiv) and MeOH (10 mL), and the mixture was heated at 70 for 2 h. After the solvent was removed by a rotary evaporator, the solid residue was treated with 1 N NaOH (30 mL), and the resulting mixture was extracted with EtOAc (4x50 mL) and dried. Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM) to give cinnamyl amine. Compound 117 (white solid) was obtained at 30% yield, and compound 119 (off-white solid) was obtained at 80% yield. Identity was confirmed by 1 H NMR (400 MHz, CD3OD).

Reference： [1]Malek, Nancy J.; Moormann, Alan E. [Journal of Organic Chemistry, 1982, vol. 47, # 27, p. 5395 - 5397]
[2]Current Patent Assignee: DUKE UNIVERSITY - WO2011/103189, 2011, A1 Location in patent: Page/Page column 78; 92-93

8
[ 5428-09-1 ]
[ 201230-82-2 ]
[ 3598-60-5 ]
2-methyl-3-N-phthalimidopropanal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With carbonylhydridetris(triphenylphosphine)rhodium(I); 4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane; hydrogen In benzene at 70℃; for 19h;
	With hydrogen; palladium diacetate; C₃₉H₃₂I₂OP₂Pd In toluene at 70℃; for 16h; Autoclave;

Reference： [1]Delogu, Giovanna; Faedda, Giovanni; Gladiali, Serafino [Journal of Organometallic Chemistry, 1984, vol. 268, # 2, p. 167 - 174]
[2]Zhang, Yang; Torker, Sebastian; Sigrist, Michel; Bregović, Nikola; Dydio, Paweł [Journal of the American Chemical Society, 2020, vol. 142, # 42, p. 18251 - 18265]

9
[ 5428-09-1 ]
[ 619-42-1 ]
[ 83665-65-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium diacetate; potassium carbonate; hydroquinone In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere; stereoselective reaction;	4.3.1. (E)-methyl 4-(3-(1,3-dioxoisoindolin-2-yl)prop-1-enyl)benzoate (3ab) General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.
70%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 100℃; for 18h;

Reference： [1]Location in patent: experimental part Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Tetrahedron, 2012, vol. 68, # 24, p. 4919 - 4926]
[2]Malek, Nancy J.; Moormann, Alan E. [Journal of Organic Chemistry, 1982, vol. 47, # 27, p. 5395 - 5397]

10
[ 5428-09-1 ]
[ 77415-80-6 ]
[ 77415-83-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 100℃;

Reference： [1]Johnson, Peter Y.; Wen, Jing Quan [Journal of Organic Chemistry, 1981, vol. 46, # 13, p. 2767 - 2771]

11
[ 5428-09-1 ]
(E)-2-(prop-1-enyl)-1H-isoindole-1,3(2H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) In benzene-d6 at 60℃; for 3h; Inert atmosphere;
90%	With tris(triphenylphosphine)ruthenium(II) chloride at 150℃; for 13h;
85%	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); diphenylphosphane; zinc(II) iodide; zinc In dichloromethane at 25℃; for 18h; Inert atmosphere; Schlenk technique;	The title compound was prepared by utilising Ni(dppp)Br2 (32 mg,50.0 μmol, 10 mol%), zinc powder (6.6 mg) and zinc iodide (32 mg,100 μmol, 20 mol% each). These materials were suspended in dichloromethane(0.3 mL) then Ph2PH solution (0.125 M in dichloromethane,0.2 mL, 25.0 μmol, 5 mol%) was added. 2-Allylisoindoline-1,3-dione (94 mg, 0.502 mmol, 1.0 equiv) was added at ambient temperatureand the reaction mixture was stirred for 18 h. Workup accordingto the general procedure and purification by flash columnchromatography (n-pentane/tert-butyl methyl ether, 20:1) gave 6d asa single E-isomer. Yield: 80 mg (0.426 mmol, 85%); yellow solid.1H NMR (300 MHz, CDCl3): δ = 7.87-7.83 (m, 2 H), 7.75-7.70 (m, 2 H),6.64-6.53 (m, 2 H), 1.84 (d, J = 5.0 Hz, 3 H).13C NMR (76 MHz, CDCl3): δ = 168.8, 134.4, 131.9, 123.6, 118.5, 118.3,16.4.

67%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; tetrahydroxydiboron In 1,2-dichloro-ethane at 40℃; for 8h; Inert atmosphere; stereoselective reaction;
60%	With tris(triphenylphosphine)ruthenium(II) chloride at 150℃; for 13h;
58%	With tris(triphenylphosphine)ruthenium(II) chloride at 150℃; for 12h; Sealed tube; Inert atmosphere;
58%	With tris(triphenylphosphine)ruthenium(II) chloride at 150℃; for 12h; Sealed tube; Inert atmosphere;
52%	With 1-C₁₀H₇Ni(P(C₆H₅)3)2Br In methanol at 50℃; for 120h;
47%	With tetrakis(triphenylphosphine)nickel⁽⁰⁾ In methanol at 60℃; Inert atmosphere; Schlenk technique;
100 % de	With palladium (II) acetate; bis(pinacol)diborane; tricyclohexylphosphine In toluene at 80℃; for 12h; Sealed tube; Inert atmosphere;

Reference： [1]Location in patent: experimental part Bujak, Piotr; Krompiec, Stanisław; Malarz, Joanna; Krompiec, Michał; Filapek, Michał; Danikiewicz, Witold; Kania, Magdalena; Gbarowska, Katarzyna; Grudzka, Iwona [Tetrahedron, 2010, vol. 66, # 32, p. 5972 - 5981]
[2]Delogu, Giovanna; Faedda, Giovanni; Gladiali, Serafino [Journal of Organometallic Chemistry, 1984, vol. 268, # 2, p. 167 - 174]
[3]Weber, Felicia; Steinlandt, Philipp S.; Ballmann, Monika; Hilt, Gerhard [Synthesis, 2017, vol. 49, # 2, p. 440 - 450]
[4]Ding, Linglong; Niu, Yan-Ning; Xia, Xiao-Feng [Journal of Organic Chemistry, 2021, vol. 86, # 15, p. 10032 - 10042]
[5]Stojanovic, Aleksandar; Renaud, Philippe; Schenk, Kurt [Helvetica Chimica Acta, 1998, vol. 81, # 2, p. 268 - 284]
[6]De-Nanteuil, Florian; Waser, Jerome [Angewandte Chemie - International Edition, 2013, vol. 52, # 34, p. 9009 - 9013][Angew. Chem., 2013, vol. 125, # 34, p. 9179 - 9183,5]
[7]Waser, Jerome; Perrotta, Daniele; Racine, Sophie; Vuilleumier, Jeremy; De Nanteuil, Florian [Organic Letters, 2015, vol. 17, # 4, p. 1030 - 1033]
[8]Halli, Juliette; Kramer, Philipp; Bechthold, Maren; Manolikakes, Georg [Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3321 - 3324]
[9]Wang, Lu; Liu, Chao; Bai, Ruopeng; Pan, Yani; Lei, Aiwen [Chemical Communications, 2013, vol. 49, # 72, p. 7923 - 7925]
[10]Ojha, Devi Prasan; Gadde, Karthik; Prabhu, Kandikere Ramaiah [Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4859 - 4865]

12
[ 5428-09-1 ]
2-allyl-2,3-dihydro-3-hydroxy-isoindol-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 3-phthalimido-1-propene With potassium hydroxide In N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere; Schlenk technique; Stage #2: With ammonium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 1h; chemoselective reaction;
91%	With N,N,N,N,-tetramethylethylenediamine; Triethoxysilane; zinc(II) acetate dihydrate In tetrahydrofuran at 70℃; Inert atmosphere; regioselective reaction;
85%	With sodium tetrahydroborate In methanol at 0℃; for 3h;

78%	With ethanol; tetrabutylammonium tetrafluoroborate; diisopropylamine at 20℃; for 2h; Electrochemical reaction; Schlenk technique; Green chemistry; chemoselective reaction;
	With sodium tetrahydroborate In methanol at -5 - 0℃;
	With methanol; sodium tetrahydroborate at 0℃; Inert atmosphere; Schlenk technique; regioselective reaction;
	With sodium tetrahydroborate In 1,4-dioxane; methanol at -5℃; for 0.166667h;

Reference： [1]Ding, Guangni; Li, Chengjun; Shen, Yifan; Lu, Bin; Zhang, Zhaoguo; Xie, Xiaomin [Advanced Synthesis and Catalysis, 2016, vol. 358, # 8, p. 1241 - 1250]
[2]Ding, Guangni; Lu, Bin; Li, Yuyuan; Wan, Jun; Zhang, Zhaoguo; Xie, Xiaomin [Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 1013 - 1021]
[3]Hitchings, Gregory J.; Helliwell, Madeleine; Vernon, John M. [Journal of the Chemical Society. Perkin transactions I, 1990, # 1, p. 83 - 87]
[4]Bai, Ya; Shi, Lingling; Zheng, Lianyou; Ning, Shulin; Che, Xin; Zhang, Zhuoqi; Xiang, Jinbao [Organic Letters, 2021, vol. 23, # 6, p. 2298 - 2302]
[5]Pin, Frederic; Comesse, Sebastien; Garrigues, Bernard; Marchalin, Stefan; Daich, Adam [Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1181 - 1191]
[6]Maity, Arnab Kumar; Roy, Sujit [Advanced Synthesis and Catalysis, 2014, vol. 356, # 11-12, p. 2627 - 2642]
[7]Sahu, Archana Kumari; Saikia, Anil K.; Shit, Sudip; Unnava, Ramanjaneyulu [Journal of Organic Chemistry, 2020, vol. 85, # 4, p. 1961 - 1971]

13
[ 591-87-7 ]
[ 1074-82-4 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	In N,N-dimethyl-formamide at 100℃; for 5h;
73%	With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 19h;

Reference： [1]Inoue, Yoshio; Taguchi, Masaaki; Toyofuku, Masanori; Hashimoto, Harukichi [Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 10, p. 3021 - 3022]
[2]Jumnah, Roshan; Williams, Jonathan M. J.; Williams, Andrew C. [Tetrahedron Letters, 1993, vol. 34, # 41, p. 6619 - 6622]

14
[ 5428-09-1 ]
[ 25316-59-0 ]
[ 74592-04-4 ]

Reference： [1]Synthesis,1995,p. 245 - 247

15
[ 5428-09-1 ]
[ 5455-98-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane
92%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 72h;
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16h;

Reference： [1]Carruthers, Nicholas I.; Spitler, James M.; Wong, Shing-Chun; Blythin, David J.; Chen, Xiao; Shue, Ho-Jane; She, Hoyan S.; Lee, Joe F.; Rizzo, Charles; Ting, Pauline C.; West Jr., Robert E. [Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 21, p. 3059 - 3064]
[2]Heyes; Niculescu-Duvaz; Cooper; Springer [Journal of Medicinal Chemistry, 2002, vol. 45, # 1, p. 99 - 114]
[3]Panek, Dawid; Wiȩckowska, Anna; Pasieka, Anna; Godyń, Justyna; Jończyk, Jakub; Bajda, Marek; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara [Molecules, 2018, vol. 23, # 2]

16
[ 5428-09-1 ]
[ 56817-84-6 ]
[ 226920-42-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dilauryl peroxide In 1,2-dichloro-ethane for 7h; Reflux;	1 General procedure for synthesis of O-ethyl S-2-phthalimidoalkyl xanthates 5 General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.
82%	With dilauryl peroxide In cyclohexane Heating;
	With dilauryl peroxide In 1,2-dichloro-ethane Reflux;

Reference： [1]Kakaei, Saeed; Chen, Ning; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 1, p. 302 - 309]
[2]Boivin, Jean; Pothier, Julien; Zard, Samir Z. [Tetrahedron Letters, 1999, vol. 40, # 19, p. 3701 - 3704]
[3]Kakaei, Saeed; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 43, p. 9068 - 9075]

17
[ 5428-09-1 ]
[ 59099-58-0 ]
2-[3-(2-methoxy-phenyl)-allyl]-isoindole-1,3-dione [ No CAS ]
2-(2-(2-methoxyphenyl)allyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 544 - 549

18
[ 5428-09-1 ]
[ 123972-89-4 ]
[ 479421-16-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dilauryl peroxide In 1,2-dichloro-ethane for 7h; Reflux;	1 General procedure for synthesis of O-ethyl S-2-phthalimidoalkyl xanthates 5 General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.
83%	With DLP In 1,2-dichloro-ethane for 2h; Heating;
	With dilauryl peroxide In 1,2-dichloro-ethane Reflux;

Reference： [1]Kakaei, Saeed; Chen, Ning; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 1, p. 302 - 309]
[2]Dublanchet, Anne-Claude; Lusinchi, Marie; Zard, Samir Z [Tetrahedron, 2002, vol. 58, # 28, p. 5715 - 5721]
[3]Kakaei, Saeed; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 43, p. 9068 - 9075]

19
[ 5428-09-1 ]
[ 201230-82-2 ]
[ 574-61-8 ]
[ 15741-71-6 ]

Yield	Reaction Conditions	Operation in experiment
46%	With hydrogen; toluene-4-sulfonic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 60 - 100℃; for 68h;

Reference： [1]Koehling, Petra; Schmidt, Axel M.; Eilbracht, Peter [Organic Letters, 2003, vol. 5, # 18, p. 3213 - 3216]

20
[ 5455-98-1 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
	With [hydrido-tris(3,5-dimethylpyrazolyl)borate]ReO₃; triphenylphosphine In benzene-d6 at 75 - 105℃; for 394h;
88 %Chromat.	With hydrogen; triethyl phosphite In isopropyl alcohol at 100℃; for 20h; Glovebox; chemoselective reaction;

Reference： [1]Gable, Kevin P.; Brown, Eric C. [Synlett, 2003, # 14, p. 2243 - 2245]
[2]Fiorio, Jhonatan L.; Rossi, Liane M. [Catalysis science and technology, 2021, vol. 11, # 1, p. 312 - 318]

21
[ 5428-09-1 ]
[ 762-72-1 ]
2-[4-(trimethylsilanyl)but-2-enyl]-1H-isoindole-1,3(2H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In dichloromethane for 48h; Heating;
78.9%	Stage #1: 3-phthalimido-1-propene; allyl-trimethyl-silane With Grubbs catalyst first generation In dichloromethane at 60℃; for 4h; Reflux; Stage #2: With tris(hydroxymethyl)phosphine In isopropyl alcohol for 12h; Reflux;	7-2 Example 7-2: Preparation of 2-(4-(trimethylsilyl)but-2-en-1-yl)isoindoline-1,3-dione I2 To a solution of 2-allylisoindoline-1,3-dione 11(13.0 g, 69.4 mmol) in CH2CI2 (500 mL) was added AIIyITMS (79.0 g, 110 mL, 694 mmol) and Grubbs I generation catalyst. The reaction was heated to 60 °C and stirred under reflux for 4 h.Tris(hydrodxymethyl)phosphine (1 M solution in i-PrOH, 58 mL) was added and stirred under reflux for 12 h, while the color of the reaction turned from black to orange. Sat. aq. NaCI solution (100 mL) was added to the reaction and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (3 x 200 mL). The combined organic layers were dried over MgSO4 and the solvent was removedunder reduced pressure. Column chromatography over SiC2 (Cyclohexane/ EtOAc =85:15) afforded the title compound (15.0 g, 54.9 mmol, 78.9 %) as a yellow resin.R: 0.57 (Cyclohexane/EtOAc = 85:15)1H NMR (300 MHz, CDCI3) 6 = -0.10-0.09 (m, 9H), 1.44 (d, J = 8.2 Hz, 1.6 H), 1.72(d, J= 8.8 Hz, 0.4 H), 4.21 (d, J= 6.5 Hz, 1.6 H), 4.29 (dd, J= 14.5, 5.9 Hz, 0.4 H),5.26 - 5.47 (m, 0.8 H), 5.56 - 5.70 (m, 0.2 H), 5.70 - 5.87 (m, 0.8 H), 5.94 - 6.09 (m,0.2 H), 7.65 - 7.74 (m, 2H), 7.79 - 7.88 (m, 2H).‘3C NMR (75 MHz, cdcl3) 6 = -2.05, -1.83, -1.43, 18.92, 22.73, 34.72, 39.87, 120.51,121.30, 123.12, 130.78, 132.24, 133.76, 133.90, 167.99.
78.9%	Stage #1: 3-phthalimido-1-propene; allyl-trimethyl-silane With Grubbs catalyst first generation In dichloromethane at 60℃; for 4h; Stage #2: With tris(hydroxymethyl)phosphine In dichloromethane; isopropyl alcohol for 12h; Reflux;	7-2 Example 7-2 Preparation of 2-(4-(trimethylsilyl)but-2-en-1-yl)isoindoline-1,3-dione 12 Example 7-2 Preparation of 2-(4-(trimethylsilyl)but-2-en-1-yl)isoindoline-1,3-dione 12 To a solution of 2-allylisoindoline-1,3-dione 11 (13.0 g, 69.4 mmol) in CH2Cl2 (500 mL) was added AllylTMS (79.0 g, 110 mL, 694 mmol) and Grubbs I generation catalyst. The reaction was heated to 60 °C and stirred under reflux for 4 h. Tris(hydrodxymethyl)phosphine (1 M solution in i-PrOH, 58 mL) was added and stirred under reflux for 12 h, while the color of the reaction turned from black to orange. Sat. aq. NaCl solution (100 mL) was added to the reaction and the organic phase was separated. The aqueous phase was extracted with CH2Cl2 (3 * 200 mL). The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. Column chromatography over SiO2 (Cyclohexane/ EtOAc = 85:15) afforded the title compound (15.0 g, 54.9 mmol, 78.9 %) as a yellow resin. Rf: 0.57 (Cyclohexane/EtOAc = 85:15) 1H NMR (300 MHz, CDCl3) δ = -0.10 - 0.09 (m, 9H), 1.44 (d, J = 8.2 Hz, 1.6 H), 1.72 (d, J = 8.8 Hz, 0.4 H), 4.21 (d, J = 6.5 Hz, 1.6 H), 4.29 (dd, J = 14.5, 5.9 Hz, 0.4 H), 5.26 - 5.47 (m, 0.8 H), 5.56 - 5.70 (m, 0.2 H), 5.70 - 5.87 (m, 0.8 H), 5.94 - 6.09 (m, 0.2 H), 7.65 - 7.74 (m, 2H), 7.79 - 7.88 (m, 2H). 13C NMR (75 MHz, cdcl3) δ = -2.05, -1.83, -1.43, 18.92, 22.73, 34.72, 39.87, 120.51, 121.30, 123.12, 130.78, 132.24, 133.76, 133.90, 167.99.

78.9%	With Grubbs catalyst first generation; tris(hydroxymethyl)phosphine In dichloromethane; isopropyl alcohol at 60℃; for 16h;	7-2 Preparation of 2-(4-(trimethylsilyl)but-2-en-1-yl)isoindoline-1,3-dione To a solution of 2-allylisoindoline-1,3-dione I1 (13.0 g, 69.4 mmol) in CH2Cl2 (500 mL) was added AllylTMS (79.0 g, 110 mL, 694 mmol) and Grubbs I generation catalyst. The reaction was heated to 60° C. and stirred under reflux for 4 h. Tris(hydrodxymethyl)phosphine (1 M solution in i-PrOH, 58 mL) was added and stirred under reflux for 12 h, while the color of the reaction turned from black to orange. Sat. aq. NaCl solution (100 mL) was added to the reaction and the organic phase was separated. The aqueous phase was extracted with CH2Cl2 (3×200 mL). The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. Column chromatography over SiO2 (Cyclohexane/EtOAc=85:15) afforded the title compound (15.0 g, 54.9 mmol, 78.9%) as a yellow resin. (0400) Rf: 0.57 (Cyclohexane/EtOAc=85:15) (0401) 1H NMR (300 MHz, CDCl3) δ=-0.10-0.09 (m, 9H), 1.44 (d, J=8.2 Hz, 1.6H), 1.72 (d, J=8.8 Hz, 0.4H), 4.21 (d, J=6.5 Hz, 1.6H), 4.29 (dd, J=14.5, 5.9 Hz, 0.4H), 5.26-5.47 (m, 0.8H), 5.56-5.70 (m, 0.2H), 5.70-5.87 (m, 0.8H), 5.94-6.09 (m, 0.2H), 7.65-7.74 (m, 2H), 7.79-7.88 (m, 2H). (0402) 13C NMR (75 MHz, cdcl3) δ=-2.05, -1.83, -1.43, 18.92, 22.73, 34.72, 39.87, 120.51, 121.30, 123.12, 130.78, 132.24, 133.76, 133.90, 167.99.
78.9%	Stage #1: 3-phthalimido-1-propene; allyl-trimethyl-silane With Grubbs catalyst first generation In dichloromethane at 60℃; for 4h; Inert atmosphere; Reflux; Stage #2: With tris(hydroxymethyl)phosphine In dichloromethane; water; isopropyl alcohol for 12h; Reflux; Inert atmosphere;

Reference： [1]Thibaudeau, Sebastien; Gouverneur, Veronique [Organic Letters, 2003, vol. 5, # 25, p. 4891 - 4893]
[2]Current Patent Assignee: MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFT E.V. - WO2015/110271, 2015, A1 Location in patent: Page/Page column 108; 110
[3]Current Patent Assignee: MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFT E.V. - EP2899192, 2015, A1 Location in patent: Paragraph 0193; 0194
[4]Current Patent Assignee: MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFT E.V. - US2017/2003, 2017, A1 Location in patent: Paragraph 0399-0402
[5]Pomplun, Sebastian; Sippel, Claudia; Hähle, Andreas; Tay, Donald; Shima, Kensuke; Klages, Alina; Ünal, Can Murat; Rieß, Benedikt; Toh, Hui Ting; Hansen, Guido; Yoon, Ho Sup; Bracher, Andreas; Preiser, Peter; Rupp, Jan; Steinert, Michael; Hausch, Felix [Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3660 - 3673]

22
[ 5428-09-1 ]
[ 78-94-4 ]
[ 160072-66-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dicyclohexylboron chloride In toluene at 80℃; for 12h;
40%	With Hoveyda-Grubbs catalyst second generation; dicyclohexylboron chloride In toluene at 80℃; for 2.5h; Inert atmosphere;

Reference： [1]Vedrenne, Emeline; Dupont, Hervé; Oualef, Sabrina; Elkaïm, Laurent; Grimaud, Laurence [Synlett, 2005, # 4, p. 670 - 672]
[2]Liu, Jiaan; Li, Yanfeng; Deol, Kirandeep K.; Strieter, Eric R. [Organic Letters, 2019, vol. 21, # 17, p. 6790 - 6794]

23
[ 5428-09-1 ]
[ 201230-82-2 ]
[ 380383-75-5 ]
[ 55747-66-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 3-phthalimido-1-propene; carbon monoxide; tert-butyl 1-(4-methoxyphenyl)hydrazine-1-carboxylate With hydrogen; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 70℃; for 68h; Stage #2: With sulfuric acid In tetrahydrofuran at 80℃; for 2h;

Reference： [1]Schmidt, Axel M.; Eilbracht, Peter [Organic and Biomolecular Chemistry, 2005, vol. 3, # 12, p. 2333 - 2343]

24
[ 5428-09-1 ]
[ 352-34-1 ]
[ 112104-03-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 110℃; for 16h; Inert atmosphere;
78%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In toluene at 110℃; for 16h; Inert atmosphere; Schlenk technique;
	With triethylamine In acetonitrile	135 2-[3-(4-fluorophenyl)-2E-propenyl]-1H-isoindole-1,3(2H)-dione STR144 Example 135 2-[3-(4-fluorophenyl)-2E-propenyl]-1H-isoindole-1,3(2H)-dione STR144 N-Allylphthalimide (13.9 g, 74.3 mmol), 1-fluoro-4-iodobenzene (15.0 g, 67.6 mmol) triethylamine (15.0 g, 148 mmol) and Pd(OAc)2 (152 mg) were heated at 104° in a glass bomb with shaking for 18 h under an inert atmosphere. The reaction mixture was dissolved in hot acetonitrile. The catalyst was removed by filtration and the filtrate cooled to 0°. The precipitated white solid product was filtered off and dried under vacuum. This title material (12.55 g) was used without further purification.

Reference： [1]Chen, Caiyou; Jin, Shicheng; Zhang, Zhefan; Wei, Biao; Wang, Heng; Zhang, Kai; Lv, Hui; Dong, Xiu-Qin; Zhang, Xumu [Journal of the American Chemical Society, 2016, vol. 138, # 29, p. 9017 - 9020]
[2][Journal of the American Chemical Society, 2017, vol. 139, # 11, p. 4230 - 4230]
[3]Current Patent Assignee: PFIZER INC - US4822775, 1989, A

25
[ 624-28-2 ]
N₂-purged [ No CAS ]
[ 5428-09-1 ]
2,5-di-(3-phthaloylaminopropyl)-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.4%	With sodium hydrogencarbonate; potassium carbonate In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide	B Step B Step B Preparation of 2,5-di-(3-phthaloylaminopropyl)-pyridine (1-2) An oven dried, N2-purged 500 mL round-bottom flask equipped with an addition funnel, N2 inlet and septum was charged with N-allylphthalimide (1-1) (1.79 g, 9.57 mmol) and 4.3 mL of anhydrous THF. The mixture was stirred for 5 minutes to dissolve the N-allylphthalimide and then cooled to 0° C. To this mixture was slowly added a 0.5M THF solution of 9-BBN (23 mL, 11.49 mmol). The resulting yellow solution was stirred overnight under N2 at room temperature (14 hrs). After stirring overnight, the flask was charged with 2,5-dibromopyridine (1.0 g, 4.31 mmol) and finely grounded K2CO3 (1.98 g, 14.35 mmol). Separately, a 25 mL flask was charged with Pd(OAc)2 (97 mg, 0.43 mmol), DPPF (286 mg, 0.54 mmol) and anhydrous DMF (10 mL). The mixture was stirred at 70° C. for 1 h and then transferred by cannula to the reaction mixture. The resulting orange/red solution was placed in an 70° C. oil bath. The reaction was stirred at the indicated temperature until completion (8-15 hrs). Upon completion, 150 mL of CH2Cl2 and 150 mL of saturated NaHCO3 were added. The organic layer was separated, washed with 150 mL of water and dried over MgSO4. The drying agent was removed by filtration and the mother liquor concentrated. Silica gel chromatography (75% EtOAc/hexane, Rf=.26) on the resulting residue yielded 1.65 g of the title compound 1-2 (84.4% yield).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US6262268, 2001, B1

26
[ 5428-09-1 ]
[ 3916-79-8 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sulfuric acid; paraformaldehyde In water	93 COMPOUND 93: A solution of paraformaldehyde (245 g) was heated to 70° C. in a solution of H2SO4 (360 mL) and H2O (90 mL) using a hot water bath until the mixture became homogenous. Solid N-allylphthalimide (133 g, 0.71 mol) was then added over 10 minutes, keeping the exotherm generated under control. The solution was then stirred at this temperature for an additional 0.5 hour and poured into ice water (1.5 L). The mixture was extracted with ethyl acetate (3*1 L), dried (MgSO4), filtered and concentrated under reduced pressure. The crude solid was then purified through a silica gel plug (1 kg SiO2) from CH2Cl2 as the eluent. This afforded the desired 1,3-dioxane-4-ylmethylphthalimide as a white solid (95 g, 54%).

Reference： [1]Current Patent Assignee: SANOFI - US2004/19058, 2004, A1

27
[ 5428-09-1 ]
[ 2216-94-6 ]
[ 1039084-37-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	With zinc(II) iodide; zinc In dichloromethane at 20℃; for 16h;

Reference： [1]Hilt, Gerhard; Paul, Anna; Harms, Klaus [Journal of Organic Chemistry, 2008, vol. 73, # 13, p. 5187 - 5190]

28
[ 5428-09-1 ]
[ 30448-78-3 ]
[ 1175163-65-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Hilt, Gerhard; Danz, Michael; Treutwein, Jonas [Organic Letters, 2009, vol. 11, # 15, p. 3322 - 3325]

29
[ 5304-21-2 ]
[ 5428-09-1 ]
2-[3-(2-methyl-benzothiazol-5-yl)-propyl]-isoindole-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		To a slurry of 2-(2-propenyl)-1H-Isoindole-1,3(2H)-dione (18.7 g, 0.1 mol) (allyl phthalimide: Journal of Organic Chemistry (1952), 17 68-76). in THF (38 ml, 2 ml/g) was added a solution (0.5 M) of 9-BBN in THF (240, 1.2 eq) over 45 minutes keeping the temperature between 0° C. and 5° C. The solution was then warmed to ambient over one hour and stirred for a further one hour. A solution of K2CO3 (27.6 g, 0.20 mol, 2 eq) in 50 ml water was added over 15 minutes, followed by 2-methyl-6-bromo-benzothiazole (20.5 g,. 0.09 mol, 0.9 eq.) dissolved in DMF (120 ml ) and Dichloro [1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (2.4 g , 0.03 eq). The reaction was warmed to 50° C. over 1 hour and then immediately cooled to ambient temperature. Water (260 ml, 19 ml/g) and t-BME (560 ml, 30 ml/g) were added and the solution stirred. The reaction was filtered through filter aid to remove any particulates. A phase separation was performed and the upper organic phase retained. The organic phase was concentrated by vacuum filtration to approximately 3 ml/g with respect to theoretical product. The dark slurry was granulated at 0° C. to -5° C. for 30 minutes, filtered under vacuum and then washed with chilled t-BME (0.4 L, 4.5 ml/g). The resulting solid was dried under vacuum at 55° C. overnight to give 2-[3-(2-methyl-benzothiazol-5-yl)-propyl]-isoindole-1,3-dione (20.5 g, 0.061 mol, 68percent)

Reference： [1]Patent: US2004/180941,2004,A1 .Location in patent: Page 21

30
[ 5428-09-1 ]
[ 1203604-04-9 ]
[ 1203605-39-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In acetonitrile at 100℃; Inert atmosphere;	82.a Under argon, a solution of [5-(4-bromo-2,6-dimethyl-phenyl)-[1,2,4]triazin-3-yl]-(5-methoxy-benzothiazol-2-ylmethyl)-amine (46 mg, 0.1 mmol, prepared as in example 79), N-allyl phtalimide (22.5 mg, 0.12 mmol, prepared as in Tetrahedron 2006, 62, 12247), triethylamine (28 µL, 0.2 mmol), tri-o-tolylphosphine (3.6 mg, 0.012 mmol), palladium(II) acetate (1.4 mg, 0.006 mmol) in degassed anhydrous acetonitrile (0.2 mL) was stirred at 100°C overnight. The reaction mixture was filtered over a pad of celite, rinsed with dichloromethane, methanol, ethyl acetate, and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 95/5) to afford 2-[3-(4-{3-[(5-methoxy-benzothiazol-2-ylmethyl)-amino]-[1,2,4]triazin-5-yl}-3,5-dimethyl-phenyl)-allyl]-isoindole-1,3-dione (43 mg, 76%) as a beige solid. ESI-MS m/z 563 (M+H)+.

Reference： [1]Current Patent Assignee: PHARMA OMNIUM INTERNATIONAL P O I - EP2141164, 2010, A1 Location in patent: Page/Page column 53-54

31
[ 5428-09-1 ]
[ 3416-57-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tert.-butylhydroperoxide; C₂₁H₁₉N₅Pd⁽²⁺⁾*2BF₄^(1-) In decane; acetonitrile at 70℃; for 24h;
79%	With palladium diacetate; Dess-Martin periodane In water; acetonitrile at 50℃; Inert atmosphere;
490 mg	With tert.-butylhydroperoxide; silver hexafluoroantimonate; [Pd(Quinox)Cl₂] In dichloromethane; water at 20℃; for 18h; Darkness;

Reference： [1]Bera, Jitendra K.; Dutta, Indranil; Kunnikuruvan, Sooraj; Reshi, Noor U Din; Saha, Sayantani; Yadav, Suman [ACS Catalysis, 2020, vol. 10, # 19, p. 11385 - 11393]
[2]Chaudhari, Dipali A.; Fernandes, Rodney A. [Journal of Organic Chemistry, 2016, vol. 81, # 5, p. 2113 - 2121]
[3]Michel, Brian W.; McCombs, Jessica R.; Winkler, Andrea; Sigman, Matthew S. [Angewandte Chemie - International Edition, 2010, vol. 49, # 40, p. 7312 - 7315]

32
[ 1074-82-4 ]
[ 107-05-1 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrabutylammomium bromide In N,N-dimethyl-formamide at 20℃; for 12.1667h; Inert atmosphere;
76%	With tetrabutylammomium bromide In N,N-dimethyl-formamide at 55℃; for 24h;
42%	With tetrabutylammomium bromide In N,N-dimethyl-formamide at 20℃; for 22h;	11 Synthesis of cinnamyl amines (117, 119); [00337] To a stirred mixture of phthalimide potassium salt (20 g, 108 mmol) and tetrabutylammonium bromide (1.04 g, 3.24 mmol, 0.03 equiv) in anhydrous DMF (75 mL) was added allyl chloride (8.84 mL, 108 mmol) at room temperature, and the mixture was stirred at room temperature for 22 h, resulting in a light-yellow suspension. The reaction was quenched by adding cold H20 (150 mL), and the mixture was stirred for 10 min (an ice bath was applied during this time to aid the precipitation). The resulting white suspension was filtered off, washed with H20 (3x50 mL), and air-dried to give N-allylphthalimide (8.5 g, 42% yield) as white solid.[00338] Aryl bromide (10 mmol), N-allylphthalimide (1.93 g, 10.3 mol, 1.03 equiv) and triethylamine (2.78 mL, 20 mmol, 2 equiv) were placed in a 50 mL three-necked round bottom flask, palladium acetate (23 mg, 0.1 mmol, 0.01 equiv) and tri-O-tolylphosphine (61 mg, 0.2 mmol, 0.02 equiv) were added to the flask under the flash of argon, and the whole mixture was heated at 100 (bath temperature) unde r argon and with stirring for 16 h. After the reaction mixture was cooled to ambient temperature, DCM (50 mL) and H20 (50 mL) were added, and stirred at room temperature for 10 min. The DCM layer was separated, and the aqueous layer was extracted with DCM (2x50 mL). The combined DCM layers were washed with H20 (50 mL) and brine (50 mL), and dried. The solvent was evaporated by a rotary evaporator to dryness, and the crude product was purified by flash column chromatography (eluting with 30-80% EtOAc in hexane) to afford N-cinnamyl phthalimide (116 or 118).[00339] N-cinnamyl phthalimide (3 mmol) was mixed with 65% hydrazine hydrate (6 mmol, 2 equiv) and MeOH (10 mL), and the mixture was heated at 70 for 2 h. After the solvent was removed by a rotary evaporator, the solid residue was treated with 1 N NaOH (30 mL), and the resulting mixture was extracted with EtOAc (4x50 mL) and dried. Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM) to give cinnamyl amine. Compound 117 (white solid) was obtained at 30% yield, and compound 119 (off-white solid) was obtained at 80% yield. Identity was confirmed by 1 H NMR (400 MHz, CD3OD).

Reference： [1]Location in patent: experimental part Cai, Chaoxian; Yu, Shichao; Cao, Bonan; Zhang, Xumu [Chemistry - A European Journal, 2012, vol. 18, # 32, p. 9992 - 9998]
[2]Eftaiha, Ala'a F.; Qaroush, Abdussalam K.; Hasan, Areej K.; Assaf, Khaleel I.; Al-Qaisi, Feda'a M.; Melhem, Maryam E.; Al-Maythalony, Bassem A.; Usman, Muhammad [New Journal of Chemistry, 2021, vol. 45, # 36, p. 16452 - 16460]
[3]Current Patent Assignee: DUKE UNIVERSITY - WO2011/103189, 2011, A1 Location in patent: Page/Page column 78; 92-93

33
[ 5332-24-1 ]
[ 5428-09-1 ]
[ 1380424-52-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium diacetate; potassium carbonate; hydroquinone In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere; stereoselective reaction;	4.3.7. (E)-2-(3-(Quinolin-3-yl)allyl)isoindoline-1,3-dione (3rb) General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

Reference： [1]Location in patent: experimental part Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Tetrahedron, 2012, vol. 68, # 24, p. 4919 - 4926]

34
[ 1532-97-4 ]
[ 5428-09-1 ]
[ 1380424-53-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With palladium diacetate; potassium carbonate; hydroquinone In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere; stereoselective reaction;	4.3.8. (E)-2-(3-(Isoquinolin-4-yl)allyl)isoindoline-1,3-dione (3sb) General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

Reference： [1]Location in patent: experimental part Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Tetrahedron, 2012, vol. 68, # 24, p. 4919 - 4926]

35
[ 104-92-7 ]
[ 5428-09-1 ]
[ 77629-09-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With palladium diacetate; potassium carbonate; hydroquinone In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere; stereoselective reaction;	4.3.5. (E)-2-(3-(4-Methoxyphenyl)allyl)isoindoline-1,3-dione (3lb)^18c General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.
83%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 110℃; for 16h; Inert atmosphere;
83%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In toluene at 110℃; for 16h; Inert atmosphere; Schlenk technique;

Reference： [1]Location in patent: experimental part Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Tetrahedron, 2012, vol. 68, # 24, p. 4919 - 4926]
[2]Chen, Caiyou; Jin, Shicheng; Zhang, Zhefan; Wei, Biao; Wang, Heng; Zhang, Kai; Lv, Hui; Dong, Xiu-Qin; Zhang, Xumu [Journal of the American Chemical Society, 2016, vol. 138, # 29, p. 9017 - 9020]
[3][Journal of the American Chemical Society, 2017, vol. 139, # 11, p. 4230 - 4230]

36
[ 5428-09-1 ]
[ 106-38-7 ]
[ 22553-96-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 110℃; for 16h; Inert atmosphere;
87%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In toluene at 110℃; for 16h; Inert atmosphere; Schlenk technique;
79%	With palladium diacetate; potassium carbonate; hydroquinone In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere; stereoselective reaction;	4.3.6. (E)-2-(3-p-Tolylallyl)isoindoline-1,3-dione (3ob) General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

Reference： [1]Chen, Caiyou; Jin, Shicheng; Zhang, Zhefan; Wei, Biao; Wang, Heng; Zhang, Kai; Lv, Hui; Dong, Xiu-Qin; Zhang, Xumu [Journal of the American Chemical Society, 2016, vol. 138, # 29, p. 9017 - 9020]
[2][Journal of the American Chemical Society, 2017, vol. 139, # 11, p. 4230 - 4230]
[3]Location in patent: experimental part Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Tetrahedron, 2012, vol. 68, # 24, p. 4919 - 4926]

37
[ 5428-09-1 ]
[ 99-90-1 ]
[ 1027906-94-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With palladium diacetate; potassium carbonate; hydroquinone In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere; stereoselective reaction;	4.3.2. (E)-2-(3-(4-acetylphenyl)allyl)isoindoline-1,3-dione (3bb) General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

Reference： [1]Location in patent: experimental part Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Tetrahedron, 2012, vol. 68, # 24, p. 4919 - 4926]

38
[ 5428-09-1 ]
[ 1122-91-4 ]
[ 1380424-50-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With palladium diacetate; potassium carbonate; hydroquinone In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere; stereoselective reaction;	4.3.3. (E)-4-(3-(1,3-Dioxoisoindolin-2-yl)prop-1-enyl)benzaldehyde (3cb) General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

Reference： [1]Location in patent: experimental part Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Tetrahedron, 2012, vol. 68, # 24, p. 4919 - 4926]

39
[ 5428-09-1 ]
[ 2142-63-4 ]
[ 1380424-51-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium diacetate; potassium carbonate; hydroquinone In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere; stereoselective reaction;	4.3.4. (E)-2-(3-(3-Acetylphenyl)allyl)isoindoline-1,3-dione (3hb) General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

Reference： [1]Location in patent: experimental part Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Tetrahedron, 2012, vol. 68, # 24, p. 4919 - 4926]

40
[ 5428-09-1 ]
[ 2943-26-2 ]
[ 1415355-15-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With dilauryl peroxide; In 1,2-dichloro-ethane; for 7.0h;Reflux;	General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.

Reference： [1]Tetrahedron,2013,vol. 69,p. 302 - 309
[2]Tetrahedron,2013,vol. 69,p. 9068 - 9075

41
[ 5428-09-1 ]
[ 49762-80-3 ]
[ 1415355-16-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dilauryl peroxide In 1,2-dichloro-ethane for 7h; Reflux;	1 General procedure for synthesis of O-ethyl S-2-phthalimidoalkyl xanthates 5 General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.
	With dilauryl peroxide In 1,2-dichloro-ethane Reflux;

Reference： [1]Kakaei, Saeed; Chen, Ning; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 1, p. 302 - 309]
[2]Kakaei, Saeed; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 43, p. 9068 - 9075]

42
[ 5428-09-1 ]
[ 19194-55-9 ]
[ 1415355-17-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dilauryl peroxide In 1,2-dichloro-ethane for 7h; Reflux;	1 General procedure for synthesis of O-ethyl S-2-phthalimidoalkyl xanthates 5 General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.
84%	With dilauryl peroxide In 1,2-dichloro-ethane Inert atmosphere; Reflux;	General procedure for synthesis of O-ethyl S-3-phthalimidoalkyl xanthates 3 General procedure: A mixture of xanthate No.6 1 (562 mg, 2 mmol) and an olefin (3 mmol) in No.23 1,2-dichloroethane (1.5 mL) was degassed by vacuumized, then filled with nitrogen. The solution was then heated to reflux and No.24 dilauroyl peroxide (DLP) (1.25-10 mol %, 10-80 mg) was added per hour. The reaction was monitored by TLC until complete disappearance of the xanthate. After evaporation of the solvent, the residue was chromatographed on a silica gel column to yield the addition product No.25 3
	With dilauryl peroxide In 1,2-dichloro-ethane Reflux;

Reference： [1]Kakaei, Saeed; Chen, Ning; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 1, p. 302 - 309]
[2]Huang, Zhongyan; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 3, p. 1050 - 1056]
[3]Kakaei, Saeed; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 43, p. 9068 - 9075]

43
[ 5428-09-1 ]
[ 218966-77-9 ]
[ 1415355-18-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dilauryl peroxide In 1,2-dichloro-ethane for 7h; Reflux;	1 General procedure for synthesis of O-ethyl S-2-phthalimidoalkyl xanthates 5 General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.
	With dilauryl peroxide In 1,2-dichloro-ethane Reflux;

Reference： [1]Kakaei, Saeed; Chen, Ning; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 1, p. 302 - 309]
[2]Kakaei, Saeed; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 43, p. 9068 - 9075]

44
[ 5428-09-1 ]
[ 3278-34-0 ]
[ 1415355-19-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dilauryl peroxide; In 1,2-dichloro-ethane; for 7h;Reflux;	General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.

Reference： [1]Tetrahedron,2013,vol. 69,p. 302 - 309
[2]Tetrahedron,2013,vol. 69,p. 9068 - 9075

45
[ 66909-39-5 ]
[ 5428-09-1 ]
[ 1415355-20-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dilauryl peroxide In 1,2-dichloro-ethane for 7h; Reflux;	1 General procedure for synthesis of O-ethyl S-2-phthalimidoalkyl xanthates 5 General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.
	With dilauryl peroxide In 1,2-dichloro-ethane Reflux;

Reference： [1]Kakaei, Saeed; Chen, Ning; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 1, p. 302 - 309]
[2]Kakaei, Saeed; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 43, p. 9068 - 9075]

46
[ 5428-09-1 ]
[ 59463-54-6 ]
O-ethyl S-3-cyano-1-phthalimidomethylpropyl dithiocarbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With dilauryl peroxide In 1,2-dichloro-ethane for 7h; Reflux;	1 General procedure for synthesis of O-ethyl S-2-phthalimidoalkyl xanthates 5 General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol %) was added and additional DLP (5 mol %) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.
	With dilauryl peroxide In 1,2-dichloro-ethane Reflux;

Reference： [1]Kakaei, Saeed; Chen, Ning; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 1, p. 302 - 309]
[2]Kakaei, Saeed; Xu, Jiaxi [Tetrahedron, 2013, vol. 69, # 43, p. 9068 - 9075]

47
[ 554-14-3 ]
[ 5428-09-1 ]
[ 1436419-44-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper diacetate; palladium diacetate; silver carbonate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 120℃; for 14h; regioselective reaction;
80%	With acridine; iron(II) phthalocyanine; oxygen; palladium diacetate; acetic acid; p-benzoquinone In 1,4-dioxane at 70℃; for 24h; Schlenk technique; Green chemistry; regioselective reaction;

Reference： [1]Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Cai, Zhongzheng; Tang, Weijun; Li, Huanrong; Xu, Lijin; Xiao, Jianliang [Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3225 - 3230]
[2]Gigant, Nicolas; Bäckvall, Jan-E. [Organic Letters, 2014, vol. 16, # 17, p. 4432 - 4435]

48
[ 1003-31-2 ]
[ 5428-09-1 ]
[ 1436419-46-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3225 - 3230

49
[ 638-02-8 ]
[ 5428-09-1 ]
[ 1436419-47-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper diacetate; palladium diacetate; silver carbonate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 120℃; for 14h; regioselective reaction;
75%	With acridine; iron(II) phthalocyanine; oxygen; palladium diacetate; acetic acid; p-benzoquinone In 1,4-dioxane at 70℃; for 24h; Schlenk technique; Green chemistry; regioselective reaction;

Reference： [1]Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Cai, Zhongzheng; Tang, Weijun; Li, Huanrong; Xu, Lijin; Xiao, Jianliang [Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3225 - 3230]
[2]Gigant, Nicolas; Bäckvall, Jan-E. [Organic Letters, 2014, vol. 16, # 17, p. 4432 - 4435]

50
[ 5428-09-1 ]
[ 201230-82-2 ]
[ 141-97-9 ]
[ 57-13-6 ]
5-ethoxycarbonyl-6-methyl-4-(3'-phthalimido-propyl)-3,4-dihydropyrimidin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With hydrogenchloride; (acetylacetonato)dicarbonylrhodium (l); hydrogen; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In ethanol at 100℃; for 24h; Inert atmosphere; Autoclave; regioselective reaction;	General procedure: The optimized hydroformylation-Biginelli reactions were performedby charging an autoclave with [Rh(CO)2acac] (2.60 mg,10.0 μmol 0.25 mol%), Xantphos (57.9 mg 100 μmol, 2.5 mol%),and urea (2, 132 mg, 2.2 mmol, 1.1 equiv) as solids under an atmosphereof argon. Subsequently, a solution of the alkene (4 mmol, 2equiv), ethyl acetoacetate (3, 0.25 mL, 260 mg, 2 mmol, 1 equiv)and concd HCl (40 μL) in EtOH (4 mL) was prepared and thentransferred into the autoclave via syringe. The autoclave was purgedthree times with syngas (CO/H2, 1:1), pressurized at 20 bar, andplaced in a preheated aluminum block at 100 °C. The reactions werestopped after 24 h by cooling the autoclave in a water bath (18 °C),venting and purging with argon. To the crude reaction mixture1,3,5-trimethoxybenzene (33.6 mg, 0.20 mmol, 0.1 equiv) as internalstandard was added and the suspension dissolved in CH2Cl2 (5mL). After evaporation of the solvents the crude product was analyzedby NMR spectroscopy and purified via flash chromatographyto yield the pure 3,4-dihydropyrimidin-2(1H)-ones 6a-l as colorlesssolids or foams

Reference： [1]Fuchs, Daniela; Nasr-Esfahani, Mahboobeh; Diab, Lisa; Šmejkal, Tomáš; Breit, Bernhard [Synlett, 2013, vol. 24, # 13, p. 1657 - 1662]

51
[ 2439-85-2 ]
[ 591-87-7 ]
[ 5428-09-1 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 6999 - 7002
Angew. Chem.,2015,vol. 127

52
[ 3481-09-2 ]
[ 106-95-6 ]
[ 5428-09-1 ]

Reference： [1]RSC Advances,2015,vol. 5,p. 65600 - 65603

53
[ 5428-09-1 ]
O-ethyl-1-fluoro-2,2,2-trifluoroethyl xanthate [ No CAS ]
S-(1-(1,3-dioxoisoindolin-2-yl)-4,5,5,5-tetrafluoropentan-2-yl) O-ethyl carbonodithioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With dilauroyl peroxide In ethyl acetate Inert atmosphere; Reflux;	General Procedure for the Addition Reaction General procedure: The starting olefin (n mmol) and xanthate 7 (1.5-2 n mmol)were dissolved in n mL of EtOAc. The solution was refluxed for10 min in a preheated bath, under a nitrogen atmosphere.Dilauroyl peroxide (DLP; 10 mol% with respect to the olefin,where the amount of DLP was calculated with respect to thexanthate) was then added every hour until total conversion ofstarting material was observed (TLC). The mixture was cooledto r.t., and the solvent was removed under reduced pressure.Products 9a-k were purified by flash chromatography (all theadducts were isolated as a mixture of diastereoisomers).

Reference： [1]Clemente-Tejeda, David; Zard, Samir Z. [Synlett, 2016, vol. 27, # 1, p. 136 - 140]

54
[ 5428-09-1 ]
[ 79606-44-3 ]
C₂₄H₂₅FN₂O₃ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 573 - 583

55
[ 109306-86-7 ]
[ 5428-09-1 ]
C₂₂H₁₅BrN₂O₂ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 573 - 583

56
[ 5428-09-1 ]
[ 79606-46-5 ]
C₂₄H₂₅BrN₂O₃ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 573 - 583

57
[ 5428-09-1 ]
[ 2436-29-5 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 2700 - 2703
[2]Organic Letters,2019,vol. 21,p. 1393 - 1396

58
[ 5428-09-1 ]
C₁₁H₁₅BrO [ No CAS ]
C₂₂H₂₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile Inert atmosphere; Reflux;	118.1 Example 118 Preparation of 3-(3-(3-aminopropyl)phenyl)-2,2-dimethylpropan-1-ol Step 1: To a solution of aryl bromide 98 (0.63 g, 2.6 mmol) in acetonitrile (5 mL) was added allyl phthalimide (0.58 g, 3.1 mmol), tri-o-tolyl phosphine (0.079 g, 0.26 mmol), and palladium acetate (0.036 g, 0.16 mmol). The mixture was evacuated and purged with argon three times, then triethylamine (0.51 mL, 3.65 mmol), was added and the evacuation-purge procedure was repeated three times. The reaction was heated at reflux overnight, then diluted with aqueous NH4OAc and extracted with EtOAc. The combined organics were washed with water, aqueous NH4OAc, saturated aqueous NaHCO3 and brine, then dried over MgSO4, filtered and concentrated. Flash chromatography of the residue (5-60% EtOAc/Hexanes gradient) gave the alcohol 99 as a white solid. Yield (0.58 g, 64%). 1H NMR (400 MHz, CDCl3) δ 7.80-7.88 (m, 2H), 7.66-7.72 (m, 2H), 7.10-7.22 (m, 3H), 7.0-7.04 (m, 1H), 6.62 (d, J=16 Hz, 1H), 6.18-6.26 (m, 1H), 4.42 (dd, J=1.6, 6.8 Hz, 2H), 3.27 (s, 2H), 2.52 (s, 2H), 1.59 (brs, 1H), 0.85 (s, 6H).

Reference： [1]Current Patent Assignee: KUBOTA PHARMACEUTICAL HOLDINGS CO LTD - US2016/193181, 2016, A1 Location in patent: Paragraph 1797-1798

59
[ 5428-09-1 ]
[ 998-30-1 ]
2-(3-(triethoxysilyl)propyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.5%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In benzene at 50 - 70℃; for 10h; Inert atmosphere;	1.2 Under nitrogen atmosphere, in 250 ml adding three-necked bottle 9.35g (0.05mol) A1 and 150 ml benzene, after stirring to dissolve by adding 0.2 ml the mass fraction is 0.520% of the Karstedt catalyst is, 50 °C activated 30 min, then add 8.2g (0.05mol) triethoxy silane, the temperature is increased to 70 °C, reaction 10h evaporating the solvent to obtain gray oily liquid, using dichloromethane: methanol = 1:3(V/V) column to obtain the product (A2) 16.2g, yield of 92.5%.
93 %Spectr.	With (dicyclopentadiene)platinum(II) dichloride at 85℃; for 20h; Inert atmosphere; Schlenk technique;	General procedure of the hydrosilylation of aminated alkene General procedure: Equimolar amounts of triethoxysilane and a respective aminated alkene were stirred with 330 ppm Cp2PtCl2 (i.e., 330 µmol per mol of silane) without solvent at 85 °C in a sealed schlenk tube under argon. After cooled to room temperature, the crude was purified by vacuum distillation or silica gel column chromatography to afford the desired product. The yield and the selectivity (i.e., the ratio of γ-isomer/β-isomer) were calculated on the basis of 1H NMR spectrum.

Reference： [1]Current Patent Assignee: NANCHANG UNIVERSITY - CN105669738, 2016, A Location in patent: Paragraph 0025
[2]Wu, Huarui; Zheng, Chaoyue; Chen, Naiwu; Zhu, Jie; Gao, Deqing [Tetrahedron Letters, 2017, vol. 58, # 16, p. 1576 - 1578]

60
[ 5428-09-1 ]
[ 1466-76-8 ]
(E)-2-(3-(2,6-dimethoxyphenyl)allyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium(II) trifluoroacetate; silver carbonate; In tetrahydrofuran; dimethyl sulfoxide; at 100℃; for 8h;Inert atmosphere;	General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Tetrahedron,2017,vol. 73,p. 2242 - 2249

61
[ 5428-09-1 ]
[ 570-02-5 ]
(E)-2-(3-(2,4,6-trimethoxyphenyl)allyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium(II) trifluoroacetate; silver carbonate; In tetrahydrofuran; dimethyl sulfoxide; at 100℃; for 8h;Inert atmosphere;	General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Tetrahedron,2017,vol. 73,p. 2242 - 2249

62
[ 5428-09-1 ]
[ 490-64-2 ]
(E)-2-(3-(2,4,5-trimethoxyphenyl)allyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction;	4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Qin, Xubo; Chen, Changjun; Zhang, Lingjuan; Xu, Jianbin; Pan, Yixiao; Zhao, Haoqiang; Han, Jiahong; Li, Huanrong; Xu, Lijin [Tetrahedron, 2017, vol. 73, # 16, p. 2242 - 2249]

63
[ 23806-24-8 ]
[ 5428-09-1 ]
(E)-2-(3-(3-methylthiophen-2-yl)allyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With palladium(II) trifluoroacetate; silver carbonate; In tetrahydrofuran; dimethyl sulfoxide; at 100℃; for 8h;Inert atmosphere;	General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Tetrahedron,2017,vol. 73,p. 2242 - 2249

64
[ 5428-09-1 ]
[ 26020-48-4 ]
(E)-2-(3-(3,4,5-trichlorothiophen-2-yl)allyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction;	4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Qin, Xubo; Chen, Changjun; Zhang, Lingjuan; Xu, Jianbin; Pan, Yixiao; Zhao, Haoqiang; Han, Jiahong; Li, Huanrong; Xu, Lijin [Tetrahedron, 2017, vol. 73, # 16, p. 2242 - 2249]

65
[ 3133-78-6 ]
[ 5428-09-1 ]
(E)-2-(3-(3-methylbenzo[b]thiophen-2-yl)allyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction;	4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Qin, Xubo; Chen, Changjun; Zhang, Lingjuan; Xu, Jianbin; Pan, Yixiao; Zhao, Haoqiang; Han, Jiahong; Li, Huanrong; Xu, Lijin [Tetrahedron, 2017, vol. 73, # 16, p. 2242 - 2249]

66
[ 5428-09-1 ]
[ 602-94-8 ]
[ 1436419-61-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction;	4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.

Reference： [1]Qin, Xubo; Chen, Changjun; Zhang, Lingjuan; Xu, Jianbin; Pan, Yixiao; Zhao, Haoqiang; Han, Jiahong; Li, Huanrong; Xu, Lijin [Tetrahedron, 2017, vol. 73, # 16, p. 2242 - 2249]

67
[ 5428-09-1 ]
[ 1092445-02-7 ]
S-(4-(2-chloropyridin-3-yl)-1-(1,3-dioxoisoindolin-2-yl)butan-2-yl)-O-ethyl carbonodithioate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3895 - 3898

68
[ 5428-09-1 ]
[ 1092445-02-7 ]
2-((1-chloro-6,7-dihydro-5H-cyclopenta[c]pyridin-5-yl)methyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3895 - 3898

69
[ 5428-09-1 ]
[ 104713-12-4 ]
C₁₈H₁₅NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 14h; Reflux;	Allylic alcohol 30 A solution of 27 (491 mg, 3.66 mmol) and N-allylphthalimide (3.43 g, 18.3 mmol) in dichloromethane(28 mL) was transferred via cannula to a flask containing Grubbs’ 2nd generation catalyst (31 mg,0.037 mmol). The resulting mixture was heated to reflux for 14 h, then concentrated in vacuo.Purification by flash chromatography (24:1-17:3 dichloromethane/ethyl acetate) provided 30 as a white solid (554 mg, 52%);

Reference： [1]Cheerlavancha, Raju; Ahmed, Ahmed; Leung, Yun Cheuk; Lawer, Aggie; Liu, Qing-Quan; Cagnes, Marina; Jang, Hee-Chan; Hu, Xiang-Guo; Hunter, Luke [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2316 - 2325]

70
[ 5428-09-1 ]
(R)-1-(4-nitrophenyl)-2-propen-1-ol [ No CAS ]
C₁₈H₁₄N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 16h; Reflux;	Allylic alcohol 36 A solution of Grubbs 2nd generation catalyst (376 mg, 0.44 mmol) in anhydrous dichloromethane(320 mL) was added via cannula to a stirred mixture of 35 (5.3 g, 29.5 mmol) and N-allylphthalimide(27.6 g, 148 mmol) in anhydrous dichloromethane (200 mL). The resulting mixture was then heated toreflux for 16 h. Dichloromethane (200 mL) was added and the mixture was filtered and concentrated invacuo. The crude solid product was washed with ethyl acetate/hexane (1:3, 200 mL) and then furtherpurified by flash chromatography (9:1→7:3 dichloromethane/ethyl acetate) to give allylic alcohol 36[1]as an off white powder (6.5 g, 65%);

Reference： [1]Cheerlavancha, Raju; Ahmed, Ahmed; Leung, Yun Cheuk; Lawer, Aggie; Liu, Qing-Quan; Cagnes, Marina; Jang, Hee-Chan; Hu, Xiang-Guo; Hunter, Luke [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2316 - 2325]

71
[ 5428-09-1 ]
[ 873-75-6 ]
4-(3-phthalimido-1-propenyl)benzyl alcohol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 100 - 110℃; for 18h;	R.20 REFERENTIAL EXAMPLE 20 REFERENTIAL EXAMPLE 20 To a mixture comprising 30.9 g of N-allylphthalimide [Nancy J. Malek and A. E. Moormaun, J. Org. Chem., 47, 5395-5397 (1982)], 30.0 g of 4-bromobenzyl alcohol, 0.36 g of palladium acetate, and 0.98 g of tri-o-tolylphosphine, were added 44.7 ml of triethylamine and 21.0 ml of acetonitrile. After flushing the vessel with nitrogen, the mixture was heated with stirring at 100° to 110° C. for 18 hours. The crude reaction product was washed thoroughly with water, dissolved in hot dimethylformamide, and filtered from a finely divided black precipitate using Celite filter aid. Water was added to the filtrate and the precipitated solid substance was collected by filtration. The solid substance was washed successively with water and ethanol, and recrystallized from acetonitrile to yield 35.5 g of pale brown needle crystals of 4-(3-phthalimido-1-propenyl)benzyl alcohol; m.p. 148°-150° C.

Reference： [1]Current Patent Assignee: ASTENA HOLDINGS CO LTD; TORII TOKIO TOKYO JP - US4598077, 1986, A

72
[ 621-23-8 ]
[ 5428-09-1 ]
(E)-2-(3-(2,4,6-trimethoxyphenyl)allyl)isoindoline-1,3-dione [ No CAS ]
(E)-2-(3-(2,4,6-trimethoxyphenyl)propenyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With 3-methyl-2-(phenylthio)butanoic acid; silver(I) acetate; palladium diacetate In 1,2-dichloro-ethane at 100℃; for 24h; Sealed tube;	2.2.1 General procedure for the Pd-catalyzed C-H allylation of simple arenes General procedure: General procedure A. A stock solution of 3-methyl-2-(phenylthio)butanoic acid (L1) (0.0846 M in CH2Cl2) (300 μL, 25.0 μmol, 10 mol%) was added to a pressure tube and the solvent was allowed to evaporate at room temperature. Then, allylbenzene (33.0 μL, 0.25 mmol, 1.0 equiv) or N-allylphthalamide (46.8 mg, 0.25 mmol, 1.0 equiv), Pd(OAc)2 (5.6 mg, 25.0 μmol, 10 mol%), silver acetate (62.8 mg, 0.375 mmol, 1.5 equiv), the corresponding arene (66.0 equiv) and DCE (0.5 mL, 0.5 M) were added. The pressure tube was sealed with a screw cap and the reaction was placed in a 100 °C pre-heated oil bath and stirred for 24 h. The resulting reaction mixture was filtered through a pad of Celite, rinsed with CH2Cl2 and then concentrated under reduced pressure. The 1H NMR yield was determined by adding CH2Br2 (17.5 μL, 0.25 mmol, 1.0 equiv) as internal standard. The crude mixture was purified by column chromatography on silica gel.

Reference： [1]Naksomboon, Kananat; Álvarez-Casao, Yolanda; Uiterweerd, Michiel; Westerveld, Nick; Maciá, Beatriz; Fernández-Ibáñez, M. Ángeles [Tetrahedron Letters, 2018, vol. 59, # 4, p. 379 - 382]

73
[ 5428-09-1 ]
[ 88876-28-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,1,3,3-Tetramethyldisiloxane; tris(pentafluorophenyl)borate In 1,4-dioxane at 110℃; for 16h; Inert atmosphere; Schlenk technique;	17 General experimental procedures of tri(pentaflurophenyl)borane-catalyzed reduction of cyclicimides (1) General procedure: To the mixture of B(C6F5)3 (5.0mol%) and cyclic imides (1.0mmol) in dioxane, was added PhSiH3 (3.0mmol) slowly under an atmosphere of nitrogen. The reaction mixture was stirred and refluxed at 110°C under an atmosphere of nitrogen. After the imide was consumed completely (detected by TLC) the mixture was added with aqueous ammonia (15mL) and extracted with CH2Cl2 (10mL×3). The combined organic phase was dried over Na2SO4, after removing the solvent under vacuum, the residue was purified by column chromatography to give the product.

Reference： [1]Ding, Guangni; Wu, Xiaoyu; Lu, Bin; Lu, Wenkui; Zhang, Zhaoguo; Xie, Xiaomin [Tetrahedron, 2018, vol. 74, # 11, p. 1144 - 1150]

74
[ 5428-09-1 ]
[ 4559-70-0 ]
N-(4-diphenylphosphoryl-3-hydroxyiminobutyl)phthalimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tert.-butylnitrite; silver nitrate In ethanol at 40℃;	21 Example 21: synthesis of Ν-(4-diphenylphosphoryl-3)-hydroxyiminobutyl)phthalimide Using N-allylphthalimide and diphenylphosphine oxide as raw materials, the reaction steps are as follows:(1) Add N-allylphthalimide (0.080 g, 0.4 mmo 1) to the reaction flask.Phosphorus phenoxide (0.243 g, 1.2 mmol),Tert-butyl nitrite (0.123 g, 1.2 mmol),Silver nitrate (0.07g, 0.04 mmol),Ethanol (2.5mL), 40°C reaction;(2) TLC tracks the reaction until complete;(3) The crude product obtained after completion of the reaction was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to give the target product (yield 70%)

Reference： [1]Current Patent Assignee: CHINASUN SPECIALTY PRODUCTS - CN107573378, 2018, A Location in patent: Paragraph 0046

75
[ 5428-09-1 ]
O-ethyl S-(2-oxotetrahydrothiophen-3-yl)carbonodithioate [ No CAS ]
S-(1-(1,3-dioxoisoindolin-2-yl)-3-(2-oxotetrahydrothiophen-3-yl)propan-2-yl) O-ethyl carbonodithioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 3-phthalimido-1-propene; O-ethyl S-(2-oxotetrahydrothiophen-3-yl)carbonodithioate In ethyl acetate at 80℃; for 0.25h; Inert atmosphere; Stage #2: With dilauryl peroxide In ethyl acetate for 1h; Inert atmosphere;	S-(1-(1,3-dioxoisoindolin-2-yl)-3-(2-oxotetrahydrothiophen-3-yl)propan-2-yl) O-ethyl carbonodithioate(26) Following a slightly modified procedure,3 14 (222 mg, 1.0 mmol, 1.0 equiv) was dissolved in 1 mL of ethylacetate to obtain a 1 M solution. The solution was warmed up to 80 °C with 2-allylisoindoline-1,3-dione(374 mg, 2.0 mmol, 2.0 equiv). After 15 minutes of reflux under nitrogen, DLP (40 mg, 0.1 mmol, 0.1equiv) was added and the solution was stirred 1 hour and monitored by TLC. The crude was concentratedin vacuo and purified by flash column chromatography (PE:EtOAc 80:20 to 70:30) to afford pure 26 (370mg, 0.9 mmol, 90%) as a light yellow oil and as a mixture of diastereoisomers. Rf (PE:EtOAc 8:2) = 0.12.1H NMR (CDCl3, 400 MHz) δ 7.84-7.80 (m, 2 H, ArH), 7.73-7.69 (m, 2 H, ArH), 4.60-4.49 (m, 2 H,OCH2CH3), 4.27-4.15 (m, 1 H, CHS), 4.03-3.88 (m, 2 H, CH2N), 3.35-3.20 (m, 2 H, CH2S), 2.78-2.64 (m,1.5 H, CH2CH2S, CHCOS), 2.60-2.54 (m, 1 H, CH2CH2S), 2.28-2.18 (m, 1 H, CHCH2CH), 2.05-1.95 (m,0.5 H, CH2CHS), 1.92-1.81 (m, 0.5 H, CH2CH2S), 1.75-1.65 (m, 1 H, CHCH2CH), 1.38 (t, 1.5 H, J = 7.1Hz, OCH2CH3), 1.37 (t, 1.5 H, J = 7.1 Hz, OCH2CH3). 13C NMR (CDCl3, 101 MHz) δ 212.5 (CS2), 212.3(CS2), 209.3 (COS), 209.2 (COS), 168.1 (N(CO)2), 134.2 (ArH), 131.7 (Ar), 123.5 (ArH), 70.6 (OCH2CH3),70.4 (OCH2CH3), 49.5 (CHCOS), 48.3 (CHS), 41.8 (CH2N), 40.3 (CH2N), 32.7 (CH2CH2S), 32.4(CH2CH2S), 32.1 (CHCH2CH), 31.8 (CHCH2CH), 30.3 (CH2CH2S), 30.2 (CH2CH2S), 13.7 (OCH2CH3).COSY, HSQC and HMBC were consistent with this attribution. IR 1773 (NC=O), 1718 (SC=O, NC=O),1223 (SC-O), 1048 (C=S). HRMS (EI) calculated for C18H19NO4S3 [M+] 409.0476; found 409.0481, fragmentationcalculated for C15H14NO3S [M+] 288.0694; found 288.0689.

Reference： [1]Simonet-Davin, Raphaël; Zard, Samir Z. [Synlett, 2018, vol. 29, # 6, p. 815 - 819]

76
[ 39795-60-3 ]
[ 5428-09-1 ]
C₂₂H₁₆N₂O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 4797 - 4802

77
[ 5428-09-1 ]
[ 883-44-3 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4979 - 4983

78
[ 7223-50-9 ]
[ 5323-50-2 ]
[ 5428-09-1 ]

Yield	Reaction Conditions	Operation in experiment
10%Chromat.; 84%	With hydrogen; In toluene; at 110℃; under 760.051 Torr; for 4h;Schlenk technique;	General procedure: The starting alkyne 1 (0.5 mmol) and dodecane as internal standard(0.22 mmol, 50 muL) were added to a suspension of the Cu-Pd-NPs/MCM-48 catalyst (10 mg) in toluene (5 mL). All reactions werecarried out in a Schlenk-type flask, fitted with a reflux condenser andsealed with a rubber septum. The reaction flask was purged and filledwith H2 (1 atm) through a balloon connected to the flask by a needle,and then heated at 110 C. Then, the reaction mixture was centrifugedand the supernatant removed. The solvent was evaporated invacuo, and the crude product was purified by flash column chromatography(silica gel, hexane/EtOAc). The recovered solid catalyst waswashed with toluene (3 × 2 mL), dried in an oven, calcined at 150 C(4 h), and reduced in H2 atmosphere at 200 C before its reuse. The following known compounds included in Table 2 were characterizedby comparison of their chromatographic and spectroscopic data (FTIR,1H NMR, 13C NMR, and MS) with those described in the literature.Styrene (2a)18Yield: 46 mg (0.44 mmol, 89%); colorless liquid.IR (film): 3082, 3060, 3027, 1630, 1496, 1449, 992, 909, 777, 698 cm-1.1H NMR (300 MHz, CDCl3): delta = 7.35 (m, 2 H), 7.25 (m, 3 H), 6.7 (dd, J =10.8, 17.1 Hz, 1 H), 5.71 (d, J = 17.1 Hz, 1 H), 5.20 (d, J = 10.8 Hz, 1 H).13C NMR (75 MHz, CDCl3): delta = 137.5, 128.5, 127.7, 126.1, 136.9, 113.7.MS: m/z (%) = 104 (100, [M+]), 103 (40), 78 (35), 77 (17), 51 (17).

Reference： [1]Synthesis,2019,vol. 51,p. 1466 - 1472

79
[ 5428-09-1 ]
tert-butyl 3-(6-bromoimidazo[1,2-a]pyridin-3-yl)-2-(diethoxyphosphoryl)acrylate [ No CAS ]
tert-butyl 2-(diethoxyphosphoryl)-3-(6-((E)-3-(1,3-dioxoisoindolin-2-yl)prop-1-en-1-yl)imidazo[1,2-a]pyridin-3-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In acetonitrile at 110℃; for 0.5h; Inert atmosphere; Microbiological reaction;	General procedure for the synthesis of compounds 3, 6-22 General procedure: Pd(OAc)2 (2.45 mg, 0.0108 mmol, 0.05 equiv) and tri(o-tolyl)phosphine (2.98 mg, 0.0098 mmol, 0.045 equiv) were added to a solution of 1a (0.2177 mmol, 1.0 equiv), DIPEA (0.057 mL, 0.327 mmol, 1.5 equiv), benzyl acrylate (0.036 mL, 0.24 mmol, 1.1 equiv) in PCN (2 mL), and the mixture placed in pressure vial equipped with a magnetic stirring bar. The mixture was stirred for 1 min and purged with argon via a syringe. Then, MW irradiation (with initial 150 W power) was applied. The following conditions were used: 30 min, 110 °C. Afterwards, the reaction mixture was diluted with DCM (10 mL), and adsorbed on silica gel (≈ 3 g). The solvent was evaporated, and the residue was subjected to column chromatography using gradient DCM/acetone as eluent to give the product as orange oil. Depending on the products different gradients were used: for compounds 3, 6-8, 10-15 (100:0 => 70:30, for compounds 16-19, 21-22 gradient 100:0 => 40:60, for compounds 9 and 20 gradient 100:0 => 10:90).

Reference： [1]Błazewska, Katarzyna M.; Kusy, Damian; Małolepsza, Joanna; Wojciechowska, Agata [Beilstein Journal of Organic Chemistry, 2020, vol. 16, p. 15 - 21]

80
[ 5332-24-1 ]
[ 5428-09-1 ]
2-(3-(quinolin-3-yl)allyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.7%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 60 - 90℃; for 25h; Inert atmosphere;	4.3.7 General procedures for the preparation of intermediates 8a and 9a General procedure: To a mixture of compound 4 or 5 (1 eq) and 3-bromoquinoline (2 eq) in acetonitrile, Pd(OAc)2 (0.3 eq), tri-o-tolylphosphine (0.6 eq) and triethylamine (3 eq) were added. The vessel was recharged with Ar. The mixture was stirred at 60°C for 1h, and then at 90°C for another 24h. Water was added and the mixture was extracted with EtOAc. The organic layer was washed with water and brine, and evaporated to remove the solvent. The resulting mixture was dissolved with EtOAc, treated with petroleum ether, and filtered to collect the products 8a and 9a.

Reference： [1]Aldrich, Courtney; Brody, Scott; Cushman, Mark; Fan, Bing-Zhi; Hiasa, Hiroshi; Liang, Jian-Hua; Lv, Wei; Yang, Zhao-Yong [European Journal of Medicinal Chemistry, 2020, vol. 193]

81
[ 5428-09-1 ]
[ 1268524-70-4 ]
C₃₄H₃₃N₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99.2%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Methyldicyclohexylamine; tri tert-butylphosphoniumtetrafluoroborate In 1-methyl-pyrrolidin-2-one at 160℃; for 0.333333h; Microwave irradiation;	6.1 Step 1: Compound 6.2 [0324] To a solution of Pd2(dba)3 (12.0 mg, 0.01 mmol) in NMP (3.0 mL) was added Compound A (30.0 mg, 0.07 mmol), [t-Bu3PH]+BF4_ (38.5 mg, 0.20 mmol), Compound 6.1 (36.9 mg, 0.20 mmol) and Cy2NMe (15.2 mg, 0.05 mmol). The mixture was stirred at (0636) 160 °C for 20 minutes under microwave irradiation. Then the mixture was filtered, concentrated, and diluted with water (10.0 mL). The resulting solution was extracted with EtOAc (10 mL x 3) and the combined organic layer was dried over anhydrous Na2S04 and concentrated. The residue was purified by column chromatography (0-50% EtOAc in PE, Rf = 0.5) to afford the desired product (Compound 6.2) (43.0 mg, 99.2%) as a red solid. LCMS (Method A): RT =0.804 min, m/z 608.3 [M+l]+.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2020/55976, 2020, A1 Location in patent: Paragraph 0324

82
[ 6479-18-1 ]
[ 5428-09-1 ]
[ 2926-29-6 ]
2-(4,4,4-trifluoro-2-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)butyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; Sealed tube;
60%	With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h;	7 Example 6 At room temperature, p-quinoxalinone 1a (0.2 mmol), allyl benzoate (0.4 mmol), sodium trifluoromethylsulfinate (0.4 mmol), potassium peroxodisulfate (0.6 mmol), acetonitrile: water (4:1) 2.5mL, mixed evenly, then stirred at 80°C in the air for 36h. After detection by TLC until the reaction was completed, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent to obtain a crude product, which was then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 10:1, silica gel Column flash column chromatography to obtain 4f of this example as a yellow solid 43.0mg, yield 55%.
57%	With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 16h; Irradiation;	31 In a 15mL reaction tube, the photocatalyst 2,4,5,6-tetra(9-carbazolyl)-isophthalonitrile (0.002 mmol), quinoxalinone 1a (0.2 mmol), 2-allyl bis Indole-1,3-dione 2m (0.4 mmol), sodium trifluoromethanesulfinate 3a (0.4 mmol), 1,4-dioxane/water (volume ratio 6:1) 4 mL, Mix well, and then react for 16 hours in the air at room temperature under the irradiation of a 3W blue LED lamp. After the reaction was detected by TLC until the reaction was completed, ethyl acetate was added and extracted 3 times. The extract was concentrated under vacuum (0.08Mpa) to solvent-free to obtain the crude product, and then used petroleum ether and ethyl acetate in a volume ratio of 3:1 The mixed eluent was washed with silica gel column and flash column chromatography to obtain 4m of this example, which was 47.3 mg of yellow solid, and the yield was 57%.

57%

With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation;

3. General procedure for visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na General procedure: To a solution of quinoxalin-2(H)-one 1 (0.1 mmol), CF3SO2Na 3 (0.2 mmol), 4CziPN (0.001 mmol, 1 mol %), 1,4-dioxane/H 2 O (6/1, 2.5 mL) was added alkene 2 (0.2 mmol). The reaction mixture was open to the air and stirred under the irradiation of 3 W blue LEDs at room temperature for 12 h. After completion of the reaction, the solution was concentrated in vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 4.

Reference： [1]Meng, Na; Wang, Leilei; Liu, Qishun; Li, Qinyu; Lv, Yufen; Yue, Huilan; Wang, Xiaojuan; Wei, Wei [Journal of Organic Chemistry, 2020, vol. 85, # 11, p. 6888 - 6896]
[2]Current Patent Assignee: QUFU NORMAL UNIVERSITY - CN111087352, 2020, A Location in patent: Paragraph 0046-0048
[3]Current Patent Assignee: QUFU NORMAL UNIVERSITY - CN112142680, 2020, A Location in patent: Paragraph 0053
[4]Meng, Na; Lv, Yufen; Liu, Qishun; Liu, Ruisheng; Zhao, Xiaohui; Wei, Wei [Chinese Chemical Letters, 2021, vol. 32, # 1, p. 258 - 262]

83
[ 5428-09-1 ]
[ 421-83-0 ]
1-methyl-4-[(trifluoromethyl)selanyl]sulfonyl}benzene [ No CAS ]
2-(4,4,4-trifluoro-2-((trifluoromethyl)selanyl)butyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With eosin; water; triethylamine In dimethyl sulfoxide at 20℃; for 4h; Inert atmosphere; Irradiation; regioselective reaction;

Reference： [1]Jiang, Xianxing; Lei, Yingjie; Wang, Hongying; Wang, Yawen; Xu, Zhaoqing; Yang, Ju; Zhan, Yue [Green Chemistry, 2020, vol. 22, # 15, p. 4878 - 4883]

84
[ 5428-09-1 ]
[ 201230-82-2 ]
[ 3598-60-5 ]

Yield	Reaction Conditions	Operation in experiment
26%	With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen; sodium hydrogensulfite; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water at 70℃; for 1h; Inert atmosphere; Microwave irradiation; regioselective reaction;

Reference： [1]Calamante, Massimo; Dei, Filippo; Maramai, Samuele; Migliorini, Francesca; Petricci, Elena [ChemCatChem, 2021, vol. 13, # 12, p. 2794 - 2806]

85
[ 5428-09-1 ]
N-(quinolin-8-yl)but‐3‐enamide [ No CAS ]
(E)-5-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)pent-3-enamide [ No CAS ]
(Z)-5-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)pent-3-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34 % de	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 16h; Glovebox; Overall yield = 38 percent; Overall yield = 14.1 mg;	4.2. Experimental procedure General procedure: To an 8-mL scintillation vial equipped with a Teflon-coated magnetic stir bar were added the AQ-containing alkenyl amide substrate 1 (0.1 mmol) and the appropriate alkene coupling partner 2 (5.0 equiv). The vial was transferred to a glovebox, and the Grubbs II catalyst (5 mol%) and DCM (0.05 mL) were added. The vial was sealed with a screw-top septum cap, removed from the glovebox, and placed in a heating block submerged in an oil bath that was pre-heated to 40 °C. The reaction was allowed to run for 16 h and then was cooled to room temperature. The reaction mixture was loaded directly onto a PTLC plate, which was developed with a mixture of hexanes and EtOAc as the eluent.

Reference： [1]Engle, Keary M.; Li, Zi-Qi; Ni, Hui-Qi; Tran, Van T. [Tetrahedron, 2021, vol. 93]

86
[ 64-18-6 ]
[ 5428-09-1 ]
[ 3130-75-4 ]
[ 24431-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; C₂₇H₂₅O₃P; lithium chloride; palladium dichloride In 1,4-dioxane at 70℃; for 24h; Sealed tube; Overall yield = 57 percent; Overall yield = 0.0667 g; regioselective reaction;

Reference： [1]Chu, Jianxiao; Guo, Jianqiong; Ren, Wenlong; Shi, Yian; Shi, Yuan; Wang, Mingzhou; Zhou, Jintao [Organic Letters, 2022, vol. 24, # 3, p. 886 - 891]

87
[ 5428-09-1 ]
[ 109-92-2 ]
C₁₅H₁₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With Quinuclidine; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; acetic acid In acetonitrile at 20℃; for 36h; Irradiation;

Reference： [1]Li, Long-Hai; Shi, Min; Wei, Hao-Zhao; Wei, Yin [Chemical Science, 2022, vol. 13, # 5, p. 1478 - 1483]

88
[ 64-18-6 ]
[ 5428-09-1 ]
[ 24431-49-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	With acetic anhydride; C₂₇H₂₅O₃P; lithium chloride; palladium (II) chloride In 1,4-dioxane at 70℃; for 24h; Inert atmosphere;	21 Example 21. Carboxylic acid (see structural formula II-u): PdCl2 (0.0044g, 0.025mmol), LiCl (0.0212g, 0.50mmol) and ligand L (0.0214g, 0.050mmol) were added to a 2mL pressure-resistant tube, and 1.0mL of the first organic solvent 1,4-dioxygen was added Hexacyclic and 4-phthalimido-1-propene I-u (0.0936g, 0.50mmol) and acetic anhydride (0.0511g, 0.50mmol) and formic acid (0.046g, 1.0mmol), charged with Ar, reacted The reaction was placed at 70°C for 24h. It was cooled to room temperature and purified by column separation. The specific conditions are: use petroleum ether to pack the column, and the eluent is petroleum ether/ethyl acetate to obtain a white solid II-u (0.0667g, 57% yield), the melting point is 146-149 ° C, and the ratio of branched chain to straight chain is 4:1.

Reference： [1]Current Patent Assignee: UNIV CHANGZHOU - CN114315563, 2022, A Location in patent: Paragraph 0122-0126

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	5428-09-1	MDL No. :	MFCD00158662
Formula :	C₁₁H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MHHGQWMCVNQHLG-UHFFFAOYSA-N
M.W :	187.20	Pubchem ID :	224401
Synonyms :

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.09
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.86
TPSA :	37.38 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.06 cm/s

Log Po/w (iLOGP) :	1.98
Log Po/w (XLOGP3) :	1.95
Log Po/w (WLOGP) :	1.09
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	2.06
Consensus Log Po/w :	1.83

[ CAS No. 5428-09-1 ] {[proInfo.proName]}

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[ 5428-09-1 ]

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[ 5428-09-1 ]

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.41
Solubility :	0.721 mg/ml ; 0.00385 mol/l
Class :	Soluble
Log S (Ali) :	-2.36
Solubility :	0.818 mg/ml ; 0.00437 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.91
Solubility :	0.228 mg/ml ; 0.00122 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.49

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H319	Packing Group:	N/A
GHS Pictogram:

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P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
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P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
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P401
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[ CAS No. 5428-09-1 ] {[proInfo.proName]}

Quality Control of [ 5428-09-1 ]

Related Doc. of [ 5428-09-1 ]

Product Details of [ 5428-09-1 ]

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Safety of [ 5428-09-1 ]

Application In Synthesis of [ 5428-09-1 ]

[ 5428-09-1 ] Synthesis Path-Upstream 1~4

[ 5428-09-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 5428-09-1 ]

Alkenes

Amides

Related Parent Nucleus of [ 5428-09-1 ]

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Related Functional Groups of
[ 5428-09-1 ]

Related Parent Nucleus of
[ 5428-09-1 ]