Name: 1200-07-3|3-(4-Bromophenyl)acrylic acid|98%
Brand: Ambeed
SKU: A238540
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1
[ 1200-07-3 ]
[ 586-76-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dihydrogen peroxide; vanadium pentoxide; trifluoroacetic acid In water monomer; acetonitrile at 20℃; for 24h; Inert atmosphere; Green chemistry;
73%	With potassium peroxomonosulfate In water monomer; acetonitrile for 30h; Reflux;	1 5.2 General procedure for the oxidative cleavage of olefins General procedure: To a solution of the olefin (0.5-1.2 mmol) in 16 mL of acetonitrile-water (1:1) mixture at reflux was introduced oxone incrementally over the entire duration of the reaction. Progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction as judged by TLC analysis, the reaction mixture was cooled to rt, and the organic matter was extracted with ethyl acetate. The combined organic extract was dried over anhyd Na2SO4 and concentrated in vacuo. The residue was subjected to a short-pad silica gel column chromatography to isolate pure product/s. All the products were characterized by their 1H NMR spectral data.
	With potassium permanganate; anhydrous sodium carbonate

durch Oxydation;

Reference： [1]Horvat, Monika; Iskra, Jernej [Green Chemistry, 2022, vol. 24, # 5, p. 2073 - 2081]
[2]Parida, Keshaba Nanda; Moorthy, Jarugu Narasimha [Tetrahedron, 2014, vol. 70, # 13, p. 2280 - 2285]
[3]Krauss [Chemische Berichte, 1902, vol. 35, p. 2932]
[4]Krauss [Chemische Berichte, 1902, vol. 35, p. 2932]

2
[ 1200-07-3 ]
4-bromocinnamoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With phosgene In water at 20℃; for 4h;	Approach 1: Synthesis of N-cinnamoylanthranilate derivatives from cinnamic acid derivatives General procedure: Cinnamoyl chlorides - Derivatives of cinnamic acid were stirred with oxalyl chloride (5 ml g-1) for up to 4 h. The stirring time differed depending on the dissolution rate of the starting cinnamic acid derivative. For derivatives with 4-NO2 or 4-N(CH3)2 substituents, a drop of dry N,N-DMF was added to catalyze the reaction. The excess reagent was evaporated under reduced pressure. The hydroxy groups in the hydroxycinnamic acid derivatives were acetylated prior to reaction with oxalyl chloride by stirring the derivative (0.0244 mol) in acetic anhydride (5 ml g-1) and pyridine (0.5 ml) at room temperature (rt, ~20 °C) overnight. Cold water (~50 ml) was added to the mixture and stirred for further 5-10 min with cooling in an ice-water bath, and the resulting precipitate of acetoxycinnamic acid was obtained by vacuum filtration, washed with cold water and dried.Methyl N-cinnamoylanthranilates - The cinnamoyl chloride (0.014 mol) was added to a solution of excess methyl anthranilate (0.017 mol) in dry pyridine (10 ml g-1), and the mixture was stirred for an hour at rt. Cold water (250 ml) was added to the reaction mixture and the resulting precipitate was filtered and washed with cold water until free of pyridine, and was recrystallized from hot ethanol. In contrast, methyl N-hydrocinnamoylanthranilate derivatives, with a low melting point, were extracted in diethyl ether (2 × 70 ml), washed with cold water (2 × 50 ml) and the solvent evaporated under reduced pressure.N-Cinnamoylanthranilic acids - The methyl N-cinnamoylanthranilate (0.010 mol) was stirred in a mixture of THF (100 ml) and methanol (20 ml), and LiOH.H2O (0.050 mol) [LiOH dissolved in water 0.2 g per 10 ml] was added to the reaction mixture and stirred at rt overnight. The excess reagent and solvents were evaporated under reduced pressure. The crude product was dissolved in water (~350 ml) and acidified slowly to pH 4 using dilute HCl (1 M) with stirring. The precipitate was obtained by vacuumfiltration, washed with water and dried, and was recrystallized from hot aqueous ethanol (water-ethanol, 1:4). In the case of N-hydroxycinnamoylanthranilate derivatives, water was added to the resulting solution to aid crystallization.α-Methylcinnamic acid - To a mixture of benzaldehyde (5 ml, 0.0492 mol) and propionic anhydride61 (10 ml, 0.0780 mol), anhydrous sodium acetate (2.5 g) was added and heated under reflux for 4 h. Once the mixture has cooled down to rt, cold water (50 ml) was added and alkalized with saturated aqueous sodium carbonate (85 ml). The resulting solid suspension was heated up to dissolve completely, and the unreacted benzaldehyde was extracted in DCM (2 × 25 ml) and the aqueous layer was acidified with concentrated HCl (12 M) with cooling. The pale yellowish white crystals (yield 2.098 g, 26 %) of α-methylcinnamic acid was obtained by vacuum filtration, washed with little cold water (~10 ml) and dried.
72%	With thionyl chloride In dichloromethane at 0 - 20℃; for 3h;
64%	With thionyl chloride at 55℃; for 5h;

	With thionyl chloride In benzene for 3h; Heating;
	With thionyl chloride; N,N-dimethyl-formamide In chloroform for 3.5h; Heating;
	With thionyl chloride for 2h; Heating;
	With oxalyl dichloride In dichloromethane at 25℃;
	With thionyl chloride In benzene Reflux;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;	General procedure for the synthesis of thecinnamamides General procedure: Asolution of the cinnamic acid (5 mmol) and oxalyl chloride (5.5 mmol) in DCM(50 mL) and 2 drops of DMF was stirred at room temperature for 2h, untilevolution of CO2 had ceased.The DCM was removed by rotary evaporation, the residue dissolved in CHCl3(30 mL) and the CHCl3 removed by rotary evaporation to remove anyexcess oxalyl chloride. The residue wasdissolved in DCM (20 mL) and added to a stirred solution of the benzylamine(6.5 mmol) and triethylamine (7 mmol) in DCM (100 mL) at 0 °C. The reaction was stirred at room temperaturefor 1h, washed with 2M aq. HCl (30 mL), water (30 mL) and 2M aq. K2CO3(30 mL) and dried (MgSO4).Removal of the solvent gave a solid which was recrystallised fromEtOAc/petroleum ether.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Cooling with ice;	General Procedure for the Synthesis of Compounds 2a-m General procedure: To a solution of cinnamic acid (10 mmol) in dichloromethane(30 mL) in an ice bath was added a mixture of oxalyl chloride (1.5 mL, 17.5 mmol) and dimethylformamide (2drops). After the mixture was stirred for 2 h at room temperature, the solvent was removed under reduced pressure to givecinnamoyl chloride which was mixed with 3,4,5-trimethoxyphenol (1.8 g, 10 mmol) and then dissolved in boron trifluoride etherate (10 mL) and heated to reflux for 10 min. After cooling, the mixture was poured into ice water and then the precipitate was filtered and washed with water until free from acid. The resulting precipitate was washed with hexane and then with ether to obtain the corresponding chalcones 1a-m (89-97%) as orange-yellow powders. A mixture of chalcones 1a-m (10 mmol) and iodine (1.0 eq) in DMSO (25 mL) was heated toreflux for 3 h. After cooling, the mixture was poured into icewater. The precipitate was filtered and washed with saturated sodium thiosulfate solution. The residue was chromatographed on a silica gel column with hexane/EtOAc (2 : 1) as the eluent to give pure 2a-m as pale yellow solids. The preparation of 3a-j (Chart 2) were essentially according to our published procedure. 20) All the physicochemical and spectroscopic characteristics of products 2a-j and 3a-j are in agreement with those reported.20)
	With thionyl chloride at 60℃; for 3h;
	With thionyl chloride In dichloromethane at 20℃; for 24h;
	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃;
	With thionyl chloride at 60℃; for 3h;
	With oxalyl dichloride In tetrahydrofuran at 60 - 70℃; for 4h;	General procedure for the synthesis of intermediates 6e-6m General procedure: In a double necked round bottom flask (RB flask), 1.94 g(10 mmol) of the compounds 2e-2m obtained in step 1 was takenand dissolved in 30 mL of tetrahydrofuran (THF). 2 mL (20 mmol)of oxalyl chloride was subsequently added to the RB flask usingdropper. The refluxing was performed for 4 h at 60-70 C. The solutionwas dried carefully under reduced pressure using rota vapourand the product obtained was used directly in the next step
	With thionyl chloride at 60℃; for 3h;	General procedure: An 50 mL anhydrous flask was charged withmagnetic stir bar, cinnamic acid (5 mmol, 0.74 g) and SOCl2 (5 mL).After stirring at 60 C for 3 h, the redundant SOCl2 was evaporatedunder reduced pressure and then the liquid was dropwise addedinto another flask containing N-methylaniline (10 mmol, 1.07 g)dissolved in anhydrous CH2Cl2 (20 mL). The mixture was stirredfor 1 h at room temperature. The organic phase was then washedby aqueous HCl and aqueous K2CO3, then dried by anhydrousNa2SO4. After evaporating the CH2Cl2, the N-methyl-N-phenylcinnamamidewas obtained in 97% yield and used in the next stepdirectly.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃;	5.11 General procedure for the preparation of compounds 9a-n General procedure: Oxalyl chloride (2.0mmol) was added drop-wise to a stirred mixture of compounds 8a-n (1.0mmol) and DMF (0.02mmol) in dichloromethane (16mL) in room temperature for 10min, and the mixture was distilled and dissolved in dichloromethane (16mL) immediately. The solution was used for the next step without further purification.
	With thionyl chloride at 75℃; for 2h;	General procedure: Compounds A11-A15, A17, A18, A20-A22, B1-B12, C7-C10 and C13-C20 were preparedaccording to method B in Fig 1 by reaction of the corresponding acyl chloride and thecorresponding alcohol. The general procedure was as follows. The mixture of cinnamic acid orcinnamic acids with substituents on the phenyl ring (0.10 mol) and 30 mL thionyl chloridewas refluxed at 75°C for 2 h. The excess thionyl chloride was removed under reduced pressure.After the residue was dissolved in 10 mL DCM, the corresponding alcohol (10 mmol) wasadded at 0°C. The solution was stirred at 0°C for 1 h, and then washed with water (3 × 30 mL)followed by 5% Na2CO3 aqueous solution, and dried over anhydrous sodium sulfate. After filtration,the solvent was removed under reduced pressure. The residue was purified by silica gelcolumn chromatography ( 40 mm × L 40 cm) to afford the desired product.
	With thionyl chloride for 1h; Reflux; Inert atmosphere; Schlenk technique;
	With phosphorus pentachloride at 20℃; for 0.5h;	3.1 In the first step, 0.05 mol of 4-bromobenzene acrylate and 0.075 mol of phosphorus pentachloride are added to the reaction vessel.Stir the reaction at room temperature for 30 min;
	With oxalyl dichloride In tetrahydrofuran for 6h; Inert atmosphere; Cooling with ice;
	With thionyl chloride Reflux; Schlenk technique;
	With oxalyl dichloride; N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;
	With oxalyl dichloride In N,N-dimethyl-formamide at 0 - 5℃; for 1h;	8.2 In a fume hood, add 81.82g (0.008mol) of VI81.82g (0.008mol) to a pear-shaped bottle, dropwise add 0.25mL of N, N-dimethylformamide (DMF), and cool to 0-5 ° C in an ice bath. Slowly add 2.00 mL (0.021 mol) of oxalyl chloride, and the addition is completed within 10 minutes. After dripping, the ice bath was removed, and the reaction was continued for 1 h until the solution was clear, and no gas was generated in the system. Use a rotary evaporator to evaporate the excess solvent and oxalyl chloride to obtain VII8. Add 16 mL of dichloromethane to dissolve it and seal it for later use.
	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 5h;	5; 8 The synthesis process is as follows: at 0 ° C, SOCl2 (2.4 mmol) and DMF (2 drops) are added to p-bromocinnamic acid (2.0 mmol) in anhydrous DCM (5 mL), and the reaction mixture is stirred at room temperature 5h. After the reaction is completed, the substituted cinnamoyl chloride is obtained by concentration. At 0 ° C, 4-hydroxycoumarin (1.6 mmol) and DIEA (3.2 mmol) were added to dry DCM (5 mL), then p-bromocinnamoyl chloride dissolved in dry DCM (5 mL) was slowly added Into the reaction system. After 30 minutes, the reaction was moved to room temperature and proceeded. Follow the reaction by TLC until the reaction is complete. The reaction was quenched with saturated sodium bicarbonate, then extracted with ethyl acetate, washed with water and saturated sodium chloride, dried over anhydrous Na2SO4, and finally purified by column chromatography. The yield was 61.7%.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.2h;

Reference： [1]Chandrabalan, Arundhasa; McPhillie, Martin J.; Morice, Alyn H.; Boa, Andrew N.; Sadofsky, Laura R. [European Journal of Medicinal Chemistry, 2019, vol. 170, p. 141 - 156]
[2]Chang, En-Ming; Lee, Cheng-Tien; Chen, Chun-Yen; Wong, Fung Fuh; Yeh, Mou-Yung [Australian Journal of Chemistry, 2008, vol. 61, # 5, p. 342 - 349]
[3]Location in patent: experimental part Davis, Matthew C.; Groshens, Thomas J. [Synthetic Communications, 2011, vol. 41, # 2, p. 206 - 218]
[4]Sekiya, Tetsuo; Hiranuma, Hidetoshi; Hata, Shunsuke; Mizogami, Susumu; Hanazuka, Mitsuo; Yamada, Shun-ichi [Journal of Medicinal Chemistry, 1983, vol. 26, # 3, p. 411 - 416]
[5]Fujimura, Ken-Ichi; Matsumoto, Junzo; Niwa, Masashi; Kobayashi, Tadayuki; Kawashima, Yoichi; In, Yasuko; Ishida, Toshimasa [Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 8, p. 1675 - 1683]
[6]Pau, Amedeo; Boatto, Gianpiero; Asproni, Battistina; Palomba, Michele; Auzzas, Luciana; Cerri, Riccardo; Palagiano, Francesco; Filippelli, Walter; Falcone, Giuseppe; Motola, Giulia [Il Farmaco, 2000, vol. 55, # 6-7, p. 439 - 447]
[7]Location in patent: experimental part Chang, Sheng; Yin, Shi-Liang; Wang, Jian; Jing, Yong-Kui; Dong, Jin-Hua [Molecules, 2009, vol. 14, # 10, p. 4166 - 4179]
[8]Location in patent: scheme or table Kim, Dong Han; Yun, Chang Hyeon; Kim, Min Hwan; Naveen Kumar, Ch.; Yun, Bo Hee; Shin, Ji-Sun; An, Hyo Jin; Lee, Young Hun; Yun, Yong Don; Rim, Hong-Kun; Yoo, Min-Sang; Lee, Kyung-Tae; Lee, Yong Sup [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 700 - 705]
[9]King, Frank D.; Caddick, Stephen [Tetrahedron, 2013, vol. 69, # 40, p. 8592 - 8601]
[10]Chung, Shu-Ting; Chien, Pei-Yu; Huang, Wen-Hsin; Yao, Chen-Wen; Lee, An-Rong [Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 5, p. 415 - 421]
[11]Wang, Hongyan; Sun, Bin; Yang, Jun; Wang, Jitao; Mao, Pu; Yang, Liangru; Mai, Wenpeng [Journal of Chemical Research, 2014, vol. 38, # 9, p. 542 - 545]
[12]Zheng, Lewei; Huang, Hongli; Yang, Chao; Xia, Wujiong [Organic Letters, 2015, vol. 17, # 4, p. 1034 - 1037]
[13]Yildirim, Muhammet; C¸elikel, Derya; Evis, Naciye; Knight, David W.; Kariuki, Benson M. [Tetrahedron, 2015, vol. 70, # 35, p. 5674 - 5681]
[14]Mai, Wen-Peng; Sun, Gang-Chun; Wang, Ji-Tao; Song, Ge; Mao, Pu; Yang, Liang-Ru; Yuan, Jin-Wei; Xiao, Yong-Mei; Qu, Ling-Bo [Journal of Organic Chemistry, 2014, vol. 79, # 17, p. 8094 - 8102]
[15]Manral, Apra; Saini, Vikas; Meena, Poonam; Tiwari, Manisha [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6389 - 6403]
[16]Mai, Wen-Peng; Wang, Ji-Tao; Xiao, Yong-Mei; Mao, Pu; Lu, Kui [Tetrahedron, 2015, vol. 71, # 42, p. 8041 - 8051]
[17]Tu, Yuanbiao; Ouyang, Yiqiang; Xu, Shan; Zhu, Yan; Li, Gen; Sun, Chao; Zheng, Pengwu; Zhu, Wufu [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 7, p. 1495 - 1503]
[18]Zhou, Kun; Chen, Dongdong; Li, Bin; Zhang, Bingyu; Miao, Fang; Zhou, Le [PLoS ONE, 2017, vol. 12, # 4]
[19]Chen, Xiangning; Gao, Bao; Su, Yijin; Huang, Hanmin [Advanced Synthesis and Catalysis, 2017, vol. 359, # 15, p. 2535 - 2541]
[20]Current Patent Assignee: SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN107382822, 2017, A Location in patent: Paragraph 0055
[21]Fokoue; Marques; Correia; Yamaguchi; Qu; Aires-De-Sousa; Scotti; Lopes; Kato [RSC Advances, 2018, vol. 8, # 38, p. 21407 - 21413]
[22]Shen, Yue; Chai, Jun; Yang, Gaosheng; Chen, Wenlong; Chai, Zhuo [Journal of Organic Chemistry, 2018, vol. 83, # 20, p. 12549 - 12558]
[23]Gao, Cheng-Zhi; Dong, Wei; Cui, Zhi-Wen; Yuan, Qiong; Hu, Xia-Min; Wu, Qing-Ming; Han, Xianlin; Xu, Yao; Min, Zhen-Li [Journal of Enzyme Inhibition and Medicinal Chemistry, 2019, vol. 34, # 1, p. 150 - 162]
[24]Current Patent Assignee: WUHAN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN110272412, 2019, A Location in patent: Paragraph 0098; 0103
[25]Current Patent Assignee: INT HEALTHCARE INNOVATION INSTITUTE JIANGMEN; WUYI UNIVERSITY - CN111057036, 2020, A Location in patent: Paragraph 0051-0053; 0063-0065
[26]Chen, Xia; Zhong, Cheng; Lu, Yuling; Yao, Meng; Guan, Zhenhua; Chen, Chunmei; Zhu, Hucheng; Luo, Zengwei; Zhang, Yonghui [Chemical Communications, 2021, vol. 57, # 42, p. 5155 - 5158]

3
[ 1200-07-3 ]
[ 25574-11-2 ]

Yield	Reaction Conditions	Operation in experiment
73.1%	With lithium aluminium tetrahydride In diethyl ether for 48h;
	With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating;
	With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Reflux;

With D-Glucose; Escherichia coli endogenous alcohol dehydrogenase; Segniliparus rugosus carboxylic acid reductase; dimethyl sulfoxide; magnesium chloride In aq. phosphate buffer at 30℃; for 18h; Enzymatic reaction;

Reference： [1]Oelschlaeger; Ewald [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 113 - 119]
[2]Glover, Stephen A.; Rowbottom, Colleen A.; Scott, Anthony P.; Schoonraad, Johan L. [Tetrahedron, 1990, vol. 46, # 20, p. 7247 - 7262]
[3]Pan, Xiang-Qiang; Wang, Lu; Zou, Jian-Ping; Zhang, Wei [Chemical Communications, 2011, vol. 47, # 27, p. 7875 - 7877]
[4]Aleku, Godwin A.; Leys, David; Roberts, George W. [Green Chemistry, 2020, vol. 22, # 12, p. 3927 - 3939]

4
[ 1200-07-3 ]
[ 75212-27-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 3-(4-bromophenyl)acrylic acid With pyridine; thionyl chloride In chlorobenzene for 72h; Reflux; Stage #2: In chlorobenzene for 2h; Reflux;
41%	With pyridine; thionyl chloride In chlorobenzene for 72h; Reflux; Inert atmosphere;
39%	With pyridine; thionyl chloride In chlorobenzene for 72h; Heating;

	With pyridine; thionyl chloride In chlorobenzene at 50 - 115℃;
	With pyridine; thionyl chloride; N,N-dimethyl-formamide at 140℃; for 2h;

Reference： [1]Sarker, Majher; Shahrin, Tasnuva; Steinmetz, Mark G. [Organic Letters, 2011, vol. 13, # 5, p. 872 - 875]
[2]Abdel-Megeed, Ashraf M.; Avery, Vicky M.; Baell, Jonathan B.; Brown, Ronald W.; Hyland, Christopher J. T.; Jones, Amy J.; Kaiser, Marcel; Keller, Paul A.; Sykes, Melissa L. [2020, vol. 11, # 12]
[3]Cross; Dickinson; Parry; Randall [Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1643 - 1650]
[4]Location in patent: scheme or table Kuduk, Scott D.; Chang, Ronald K.; Di Marco, Christina N.; Dipardo, Robert M.; Cook, Sean P.; Cato, Matthew J.; Jovanovska, Aneta; Urban, Mark O.; Leitl, Michael; Spencer, Robert H.; Kane, Stefanie A.; Hartman, George D.; Bilodeau, Mark T. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 14, p. 4255 - 4258]
[5]Irgashev, Roman A.; Karmatsky, Arseny A.; Rusinov, Gennady L.; Charushin, Valery N. [Organic Letters, 2016, vol. 18, # 4, p. 804 - 807]

5
[ 141-82-2 ]
[ 1122-91-4 ]
[ 1200-07-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100 - 110℃; for 1.33333h;	Preparation of cinnamic acids: General procedure: To aromatic aldehyde (500 mg, 1.0 equiv) and malonic acid (981 mg, 2.0 equiv) was added DABCO (105 mg, 2 equiv) in dimethyl formamide (5 mL) and the reaction mixture was stirred at 100-110 °C for 60-90 min. After completion of the reaction (TLC monitoring), reaction mixture was poured in water and then extracted with ethyl acetate. Crude product was recrystallized from chloroform/hexane system to provide cinnamic acids in good yield.
87%	With pyridine; aniline at 60℃; Reflux;
85%	Stage #1: malonic acid; 4-bromo-benzaldehyde With piperidine; pyridine for 2h; Reflux; Stage #2: With hydrogenchloride In water	1 4.1.1.1 General procedure for the synthesis of 3-substituted acrylic acid General procedure: A mixture of substituted carbaldehyde (200 mmol), propenedioic acid (20.8 g, 200 mmol) in a solution of pyridine (10 ml, 120 mmol) and piperidine (1 ml) was warmed at reflux for 2 h. The resultant solution was poured into 2 M HCl aq. and then cooled to room temperature. The present solid was collected by filtration, washed with water and recrystallized from ethanol/water.

85%	With piperidine; pyridine for 2h; Reflux;
68.69%	With pyridine; ammonium acetate at 85℃; for 5h; Darkness;	8.2 Step 2: Preparation of 4-methacryloylpiperazine (IX7) A 50 mL round bottom flask with a reflux condenser was charged with 4.39 g (0.024 mol) of 4-bromobenzaldehyde, 4.90 g (0.047 mol) of malonic acid, 0.18 g (0.023 mol) of ammonium acetate, and 16 mL of pyridine. The oil bath was heated to 85 ° C, and the reaction was refluxed for 5h in the dark. The reaction was stopped, left to cool to room temperature, and poured into 50 mL of ice water. The pH was adjusted to about 2 with dilute hydrochloric acid, and a large amount of solid was precipitated. The solid was filtered by suction, and the solid was washed with water until it had no pyridine smell. Dry to obtain a solid product. Recrystallization using anhydrous ethanol to obtain VI8 as a white solid with a yield of 68.69% and a melting point of 262.5-264.3 ° C.
	With piperidine; pyridine Heating;
	With piperidine; pyridine for 2h; Reflux;
	Stage #1: malonic acid; 4-bromo-benzaldehyde With piperidine; pyridine Reflux; Stage #2: With hydrogenchloride In water at 25℃;
	With pyridine Reflux;
	With piperidine; pyridine at 80 - 90℃; for 24h;	4.2. General procedure for synthesis of cinnamic acids General procedure: A mixture of aromatic aldehydes (3.2 mmol), malonic acid (3.87 mmol), piperidine (0.387 mmol) was dissolved in pyridine and stirred on 80-90 °C for 24 h. The pyridine was removed at the vacuum. The reaction mixture was poured in water and washed with HCl, the precipitate was filtered and washed with hexane about three times, and dried under vacuum to afford the cinnamic acids (Scheme 1).
	With piperidine; pyridine at 60 - 120℃;
	With pyridine at 100℃; for 2h;
	With piperidine; pyridine at 90 - 105℃;	General procedure for the synthesis of intermediates 2a-2m General procedure: 3 g (28.6 mmol) of malonic acid was added to a stirred solutionof (13 mmol) substituted aromatic aldehydes (1a-1m) in pyridine(30 mL) and piperidine (3 mL). The mixture was heated to temperatureof 90-105 C for 5-6 h under reflux. After cooling, the mixturewas poured into cold water and acidified with concd HCl.The precipitated white crystals were filtered, washed with 4200 mL water and dried at 45 C and were further identifiedthrough ESI-MS and NMR (overall yield 70-80%)
	With piperidine; pyridine for 20h; Reflux;	5.10 General procedure for the preparation of compounds 8a-n General procedure: To the mixture of substituted benzaldehydes 7a-n (2.5mmol), pyridine (20.0mL), piperidine (0.2mL), propanedioic acid (5.0mmol) was added at room temperature and the mixture was heated and refluxed for 20h and monitored by TLC. The reaction mixture was cooled to room temperature and the solution was acidified to pH=5 to yielding a precipitate. The mixture was filtered and washed with water to furnish the compounds 8a-n.
	With piperidine; pyridine for 1h; Reflux;
	With piperidine; pyridine at 20 - 90℃;	1.1. General methods for acrylic acids (A1-A11) General procedure: To a solution of benzaldehyde (3.00 g, 28.3 mmol) in pyridine (20 mL) at room temperature was added malonic acid (5.89 g, 58.6 mmol) and piperidine (2 drops). The resulting solution was allowed to stir at 90 °C. The reaction was monitored by TLC. After reaction completed, the solution was concentrated in vacuum to remove solvent. Then, 2 M sodium hydroxide (50 mL) was added and the resulting solution was allowed to stir at 60 °C until it completely clear. Afterwards, the solution was extracted with EtOAc (3 × 20 mL) and the aqueous layer was subsequently adjusted to pH = 1-2 by hydrochloric acid. The resulting precipitate was filtered, washed with water, dried to afford solid A1 (2.41 g, 58%). According to the above procedure, corresponding acrylic acids A2-A11 were prepared in yields ranging from 43% to 86%.
	With pyridine; ammonium acetate at 85℃; for 5h;
97 %Chromat.	With chitosan In N,N-dimethyl-formamide at 70℃; for 18h;	2.3 Reaction procedure for Knoevenagel-Doebner condensation between 1 and 2 General procedure: Chitosan (25mg), 1 (0.5mmol) and 2 (0.6mmol) were added to an oven-dried 10mL glass reactor. To this mixture, DMF (0.4mL) was added as a solvent and mixed homogeneously before placing this heterogeneous slurry in a preheated oil bath maintained at 70°C for required time mentioned as shown in Table 1. The reaction progress was monitored using Agilent 7820 A GC analysis by sampling aliquots from the reaction mixture at different time intervals. The yield of the final product was assessed by GC using internal standard method. The obtained products were confirmed by Agilent 5779 B model GC-MS instrument. Reusability test was performed by recovering the catalyst through filtration from the reaction mixture followed by washing the catalyst with HPLC grade of acetonitrile three times (5mL x 3) and dried at 80°C for 3h. This dried solid catalyst was reused in the next cycle with the fresh reactants of 1 and 2.
	With piperidine; pyridine at 130℃; for 5h;
	With piperidine; pyridine for 2h; Reflux; Schlenk technique; Inert atmosphere;
	With piperidine; pyridine Reflux; Inert atmosphere;

Reference： [1]Nagalakshmi; Diwakar; Govindh; Gopal Reddy; Venu; Bhargavi; Prasanna Devi; Murthy; Siddaiah [Asian Journal of Chemistry, 2017, vol. 29, # 7, p. 1561 - 1564]
[2]Nagarkar, Amit A.; Yasir, Mohammad; Crochet, Aurelien; Fromm, Katharina M.; Kilbinger, Andreas F. M. [Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12343 - 12346][Angew. Chem., 2016, vol. 128, p. 12531 - 12534]
[3]Zhang, Peng; Hu, Hai-Rong; Bian, Shi-Hui; Huang, Zhao-Hui; Chu, Yong; Ye, De-Yong [European Journal of Medicinal Chemistry, 2013, vol. 61, p. 95 - 103]
[4]Zhang, Peng; Min, Zhihui; Gao, Yang; Bian, Jiang; Lin, Xin; He, Jie; Ye, Deyong; Li, Yilin; Peng, Chao; Cheng, Yunfeng; Chu, Yong [Journal of Medicinal Chemistry, 2021, vol. 64, # 11, p. 7341 - 7358]
[5]Current Patent Assignee: WUHAN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN110272412, 2019, A Location in patent: Paragraph 0098-0102
[6]Pau, Amedeo; Boatto, Gianpiero; Asproni, Battistina; Palomba, Michele; Auzzas, Luciana; Cerri, Riccardo; Palagiano, Francesco; Filippelli, Walter; Falcone, Giuseppe; Motola, Giulia [Il Farmaco, 2000, vol. 55, # 6-7, p. 439 - 447]
[7]Location in patent: experimental part Li, Fu-Nan; Kim, Nam-Jung; Paek, Seung-Mann; Kwon, Do-Yeon; Min, Kyung Hoon; Jeong, Yeon-Su; Kim, Sun-Young; Park, Young-Ho; Kim, Hee-Doo; Park, Hyeung-Geun; Suh, Young-Ger [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 10, p. 3557 - 3567]
[8]Location in patent: experimental part Chang, Sheng; Yin, Shi-Liang; Wang, Jian; Jing, Yong-Kui; Dong, Jin-Hua [Molecules, 2009, vol. 14, # 10, p. 4166 - 4179]
[9]Pan, Xiang-Qiang; Wang, Lu; Zou, Jian-Ping; Zhang, Wei [Chemical Communications, 2011, vol. 47, # 27, p. 7875 - 7877]
[10]Location in patent: experimental part Zhang, Hong-Jia; Zhu, Di-Di; Li, Zi-Lin; Sun, Juan; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 15, p. 4513 - 4519]
[11]Location in patent: scheme or table Sharma, Mukul; Joshi, Mukesh C; Kumar, Vineet; Malhotra, Sanjay V.; Rawat, Diwan S. [Archiv der Pharmazie, 2011, vol. 344, # 9, p. 567 - 571]
[12]Yildirim, Muhammet; C¸elikel, Derya; Evis, Naciye; Knight, David W.; Kariuki, Benson M. [Tetrahedron, 2015, vol. 70, # 35, p. 5674 - 5681]
[13]Manral, Apra; Saini, Vikas; Meena, Poonam; Tiwari, Manisha [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6389 - 6403]
[14]Tu, Yuanbiao; Ouyang, Yiqiang; Xu, Shan; Zhu, Yan; Li, Gen; Sun, Chao; Zheng, Pengwu; Zhu, Wufu [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 7, p. 1495 - 1503]
[15]Wang, Guojin; Tang, Yu; Zhang, Yu; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming [Chemistry - A European Journal, 2017, vol. 23, # 3, p. 554 - 557]
[16]Jia, Li; Yan, Mi; Shen, Yan; Qin, Yinhui; Qiang, Shengsheng; Ma, Shutao [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3693 - 3697]
[17]Gao, Cheng-Zhi; Dong, Wei; Cui, Zhi-Wen; Yuan, Qiong; Hu, Xia-Min; Wu, Qing-Ming; Han, Xianlin; Xu, Yao; Min, Zhen-Li [Journal of Enzyme Inhibition and Medicinal Chemistry, 2019, vol. 34, # 1, p. 150 - 162]
[18]Anbu, Nagaraj; Hariharan, Surendran; Dhakshinamoorthy, Amarajothi [Molecular catalysis, 2020, vol. 484]
[19]Maeta, Naoya; Kamiya, Hidehiro; Okada, Yohei [Journal of Organic Chemistry, 2020, vol. 85, # 10, p. 6551 - 6566]
[20]Lu, Xiao-Yu; Xia, Ze-Jie; Gao, Ang; Liu, Qi-Le; Jiang, Run-Chuang; Liu, Chuang-Chuang [Journal of Organic Chemistry, 2021, vol. 86, # 13, p. 8829 - 8842]
[21]Pan, Chunxiang; Yang, Chunhui; Li, Kangkui; Zhang, Keyang; Zhu, Yuanbin; Wu, Shiyuan; Zhou, Yongyun; Fan, Baomin [Organic Letters, 2021, vol. 23, # 18, p. 7188 - 7193]

6
[ 141-82-2 ]
[ 1122-91-4 ]
[ 1200-07-3 ]
[ 39773-47-2 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 7449 - 7461

7
[ 67-56-1 ]
[ 1200-07-3 ]
methyl (E)-4-bromocinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride at 40℃; for 1.33333h; Reflux;	Esterification of 4-bromocinnamoic acid to give (methyl (E)-3-(4~bromophenyI)acryIate) 1 Thionyl chloride (176 mL, 2422 mmol) was added dropwise to a white suspension of 4-bromocinnamoic acid (500 g, 2202 mmol) in methanol (3000 mL) over 20 min during which the reaction temperature remained below 40 °C. The mixture was then heated to reflux for 1 h, during which it became homogeneous. The solution was sfowiy allowed to room temperature to give a white suspension. It was filtered and the filter cake washed two times with cold methanol to give 1 as white solid. The filtrate was concentrated to half of the original volume and was again filtered and the filter cake washed with cold methanol. The procedure was repeated two more times to give additional 1 (523 g combined, 98% yield). H NMR (400 MHz, CDCb) d 7.62 (d, J = 16.0 Hz, 1 H), 7.52 (d, J = 8.2 Hz, 2 H), 7.38 (d, J = 8.6 Hz, 2 H), 6.43 (d, J = 16.0 Hz, 1 H), 3.81 (s, 3 H); 13C NMR (75 MHz, CDCb) d 167.1, 143.4, 133 2, 132.1, 129.4, 124.5, 1 18.5, 51.8.
	With thionyl chloride at 0℃; for 3h; Heating / reflux;	7.A.a; 7.B.a; 7.C.a To a stirred solution of 4-bromocinnamic acid (16g) in methanol (150 mL) was added thionyl chloride (30 mL) at OX. The reaction mixture was warmed to room temperature and refluxed for 3 hours. After cooling to room temperature the solvents were evaporated to dryness. The crude compound obtained was used as such for the next step.

Reference： [1]Current Patent Assignee: EISAI CO LTD - WO2020/146568, 2020, A1 Location in patent: Page/Page column 31-32
[2]Current Patent Assignee: SUN PHARMACEUTICAL INDUSTRIES LIMITED - WO2008/23336, 2008, A2 Location in patent: Page/Page column 91-92; 94; 96

8
[ 1200-07-3 ]
[ 75476-86-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1333 - 1336

9
[ 1200-07-3 ]
[ 55394-81-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1333 - 1336

10
[ 1200-07-3 ]
[ 215453-51-3 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537

11
[ 1200-07-3 ]
[ 223671-15-6 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537
[3]Journal of the American Chemical Society,2015,vol. 137,p. 10464 - 10467

12
[ 1200-07-3 ]
[ 90562-10-0 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 7247 - 7262

13
C₁₃H₁₆BBrO₂ [ No CAS ]
[ 124-38-9 ]
[ 1200-07-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium <i>tert</i>-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; for 24h;

Reference： [1]Ohishi, Takeshi; Nishiura, Masayoshi; Hou, Zhaomin [Angewandte Chemie - International Edition, 2008, vol. 47, # 31, p. 5792 - 5795]

14
[ 67-56-1 ]
[ 1200-07-3 ]
methyl 4-bromocinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With thionyl chloride
83%	With sulfuric acid Reflux;
	With sulfuric acid at 20 - 75℃; for 12h;	1.1. General methods for propiolic acids (A1-A8) General procedure: To a solution of cinnamic acid (0.96 g, 6.48 mmol) in methanol (50 mL) at room temperature was added concentrated sulfuric acid (0.50 mL). The resulting solution was allowed to stir at 75 °C. The reaction was monitored by TLC. After reaction completed, the solution was diluted with water (200 mL) and the aqueous layer was extracted with dichloromethane (4×50 mL). The combined organic layer was washed with saturated NaHCO3 solution and then washed with water. The solvent was dried over anhydrous Na2SO4, filtered, and concentrated in vacuum to afford methyl cinnamate (1.03 g, 98%).

Reference： [1]Location in patent: body text Zeng, Wenbin; Miao, Weimin; Kabalka, George; Puil, Michael Le; Biggerstaff, John; Townsend, David [Tetrahedron Letters, 2008, vol. 49, # 45, p. 6429 - 6432]
[2]Nagarkar, Amit A.; Yasir, Mohammad; Crochet, Aurelien; Fromm, Katharina M.; Kilbinger, Andreas F. M. [Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12343 - 12346][Angew. Chem., 2016, vol. 128, p. 12531 - 12534]
[3]Jia, Li; Wang, Yinhu; Wang, Yanxia; Qin, Yinhui; Hu, Chaoyu; Sheng, Juzheng; Ma, Shutao [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2471 - 2476]

15
[ 1200-07-3 ]
[ 479074-63-0 ]
[ 24250-84-8 ]
[ 62561-74-4 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 9152 - 9157

16
[ 64-17-5 ]
[ 1200-07-3 ]
ethyl 4-bromocinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.2%	With sulfuric acid at 95℃;	5 Example 5 Reagents and conditions:A)EtOH, H2O, conc. H2SO4, 95 ° C overnightB)DIBAL-H, DCM, -70 ° C rt;C)NaNO2, AcOH-H2O, rt, 3h;D)Day - Martin oxidizer, DCM, rt, overnight;E)NH4OH-HCl, pyridine, EtOH, 95 ° C, 3 h;F)SOCl2, DMF, rt, overnight.Compound 23 (10 g, 44.1 mmol) was dissolved in ethanol (100 mL)Adding concentrated sulfuric acid as catalyst for stirring at 95 ° C overnight,TLC tracks the completion of the response,After completion of the reaction with sodium bicarbonate and,Ethyl acetate extraction,The solvent was removed by concentration to give compound 24 (10 g, 89.2%) as an oil;Compound 24 (10 g, 39.2 mmol, 1 eq) was dissolved in DCM,At -70 & lt; 0 & gt; C,Diba-H (1.5 M, 65 mL, 98.3 mmol, 2.5 eq) was slowly added dropwise,After dripping,Reaction at room temperature for 1h,TLC tracks the completion of the response,After completion of the reaction,At -20 ° C,Compound 25 (5 g, 60.0%) was obtained by quenching, filtering, extracting and concentrating the solvent with dilute hydrochloric acid.Compound 25 (5 g, 23.5 mmol, 1 eq) was dissolved in acetic acid (10 mL)An aqueous solution of NaNO2 (3.24 g, 46.9 mmol, 2 eq) was then slowly added,The color of the reaction solution slowly turned yellow, followed by stirring at room temperature overnight,TLC tracks the completion of the response,After the reaction, the neutral compound was extracted and concentrated to obtain the yellow compound 26 (FWH-271) (2 g, 31.4%).after that,Compound 26 (2 g, 7.4 mmol, 1 eq) was dissolved in DCM,The Days-Martin Oxidant (3.9 g, 8.8 mmol, 1.2 eq) was added,The reaction was stirred overnight at room temperature,TLC tracks the completion of the response,After the reaction, the solvent was removed by suction filtration, neutralization, extraction and concentration to give pale yellow compound 27 (1.5 g, 75%);Compound 27 (5 g, 18.6 mmol, 1 eq) was then dissolved in ethanol,Hydroxylamine hydrochloride (1.5 g, 22.3 mmol, 1.2 eq), pyridine (1.8 g, 22.3 mmol, 1.2 eq)After heating, the temperature was raised to 95 and the reaction was refluxed for 3 h,TLC tracks the completion of the response,After completion of the reaction,After concentration of ethanol,Pickling, extracting, and concentrating to remove the solvent to give yellow compound 28 (3.5 g,64.8%);after that,Compound 28 (2 g, 7.0 mmol, 1 eq) was dissolved in DMF (10 mL)Slowly dropwise SOCl2 (3.3 g, 28 mmol, 4 eq)The reaction was stirred overnight at room temperature,TLC tracks the completion of the response,After completion of the reaction, the solvent was removed by neutralization, extraction and concentration, and the product was isolated by column chromatography to give pale yellow compound 29 (FWH-266) (1.0 g, 53.5%).
	With chloro-trimethyl-silane at 25℃; for 12h; Inert atmosphere;

Reference： [1]Current Patent Assignee: JIANGSU INST PARASITIC DISEASES; JIANGNAN UNIVERSITY - CN104003954, 2017, B Location in patent: Paragraph 0091; 0092; 0093; 0094
[2]Rai, Ganesha; Sayed, Ahmed A.; Lea, Wendy A.; Luecke, Hans F.; Chakrapani, Harinath; Prast-Nielsen, Stefanie; Jadhav, Ajit; Leister, William; Shen, Min; Inglese, James; Austin, Christopher P.; Keefer, Larry; Arnér, Elias S. J.; Simeonov, Anton; Maloney, David J.; Williams, David L.; Thomas, Craig J. [Journal of Medicinal Chemistry, 2009, vol. 52, # 20, p. 6474 - 6483]

17
[ 1200-07-3 ]
3-(4-bromophenyl)prop-2-en-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41.5%	Stage #1: 3-(4-bromophenyl)acrylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate at 0℃; for 0.5h; Stage #3: With methanol at 20℃;	4 Take p-bromocinnamic acid (1.0 g, 4.4 mmol) in a two-necked flask, add 10 mL of anhydrous THF in a N2 atmosphere, and slowly drop triethylamine (0.45 g, 4.4 mmol) at 0° C. for more than 2 min. After reacting for 5 min, ClCOOCH2CH3 (0.48 g, 4.4 mmol) was slowly added dropwise for more than 5 min. A white precipitate appeared in the reaction solution, filtered, and NaBH4 (0.62g, 16.7mmol) was added to the filtrate in batches under stirring at 0°C, and reacted for more than 30 minutes. After the reaction was completed, 10 mL of methanol was slowly added to quench, and the reaction was carried out at room temperature overnight. Adjust the pH of the reaction solution to acidity with concentrated hydrochloric acid, add 10 mL of purified water, extract three times with CH2Cl2 (3×10 mL), enrich the organic layer, add anhydrous sodium sulfate and spin dry, proceed to silica gel (200 mesh-300 mesh) column layer After precipitation and separation, the eluent is petroleum ether: acetone = 7:1 or chloroform: methanol = 100:1, and the target product 1d is obtained after vacuum drying, with a yield of 41.5%.
	Multi-step reaction with 3 steps 1: thionyl chloride / 5 h / 55 °C 2: Reflux 3: diisobutylaluminium hydride / hexane; toluene / 20 °C
	Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 0.5 h / -7 °C 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 10 °C

	Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: diisobutylaluminium hydride / dichloromethane / 3 h / -78 - 0 °C
	Multi-step reaction with 2 steps 1: sulfuric acid / 95 °C 2: diisobutylaluminium hydride / dichloromethane / 1 h / -70 - 20 °C

Reference： [1]Current Patent Assignee: LISHUI VOCATIONAL TECHNICAL COLLEGE - CN111662303, 2020, A Location in patent: Paragraph 0028
[2]Davis, Matthew C.; Groshens, Thomas J. [Synthetic Communications, 2011, vol. 41, # 2, p. 206 - 218]
[3]Manral, Apra; Saini, Vikas; Meena, Poonam; Tiwari, Manisha [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6389 - 6403]
[4]Nagarkar, Amit A.; Yasir, Mohammad; Crochet, Aurelien; Fromm, Katharina M.; Kilbinger, Andreas F. M. [Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12343 - 12346][Angew. Chem., 2016, vol. 128, p. 12531 - 12534]
[5]Current Patent Assignee: JIANGSU INST PARASITIC DISEASES; JIANGNAN UNIVERSITY - CN104003954, 2017, B

18
[ 1200-07-3 ]
[ 316375-85-6 ]
[ 1268494-49-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium chromate; water; oxygen; palladium dichloride In N,N-dimethyl-formamide at 60℃; for 12h; regioselective reaction;

Reference： [1]Yang, Yuzhu; Chen, Li; Zhang, Zhaoguo; Zhang, Yuhong [Organic Letters, 2011, vol. 13, # 6, p. 1342 - 1345]

19
[ 1200-07-3 ]
[ 80793-25-5 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 7875 - 7877

20
[ 1200-07-3 ]
[ 3366-95-8 ]
[ 1326302-63-9 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

21
[ 1200-07-3 ]
[ 402-46-0 ]
[ 1332498-82-4 ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 × 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4730 - 4738

22
[ 1200-07-3 ]
[ 37073-15-7 ]
[ 1198081-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 70℃;	General procedure: A mixture of alpha,beta-unsaturated aromatic or aliphatic acid (10 mmol), CH3SO2Bt (10 mmol) and Et3N (15 mmol) were refluxed in dry THF (50 mL) overnight. The solvent was evaporated and the residue was dissolved in CH2Cl2 (100 mL). The organic phase was washed with brine (3 times) and dried over anhydrous Na2SO4. The organic phase was concentrated under vacuum to give a crude product, which could be further purified by recrystallization from a proper solvent.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4906 - 4910

23
[ 589-87-7 ]
[ 79-10-7 ]
[ 1200-07-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tributyl-amine at 110℃; for 3h;
93%	With sodium carbonate In water at 100℃; for 24h;
77%	With potassium carbonate at 80℃; Micellar solution;	A typical Heck reaction was performed in a double walledglass reactor with reflux condenser at ambient pressure. 153 μL (1.34 mmol) alkene (e.g. styrene) and 158 L (1.50 mmol) arylhalide (e.g. iodobenzene) were dissolved in 46 mL organic sol-vent or aqueous microemulsion in the presence of 0.276 g(2.00 mmol) K2CO3as base and stirred at desired reactiontemperature.1.2-1.4 g of the immobilized catalyst containing15 mg (0.067 mmol) Pd(OAc)2on silica was added to the reactionmixture and the reaction was started. For the Heck reaction withhomogeneous catalyst only 15 mg (0.067 mmol) of palladium (II)acetate was added. The reaction progress was monitored by mea-suring the reactant concentrations at different reaction times byhigh performance liquid chromatography (HPLC).

Reference： [1]Xiao, Jian; Zhang, Haonan; Ejike, Anyaegbu Chima; Wang, Lu; Tao, Minli; Zhang, Wenqin [Reactive and functional polymers, 2021, vol. 161]
[2]Location in patent: experimental part Shi, Xianying; Han, Xiaoyan; Ma, Wenjuan; Fan, Juan; Wei, Junfa [Applied Organometallic Chemistry, 2012, vol. 26, # 1, p. 16 - 20]
[3]Volovych; Kasaka; Schwarze; Nairoukh; Blum; Fanun; Avnir; Schomäcker [Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 210 - 221]

24
[ 1200-07-3 ]
caudatin [ No CAS ]
3-O-(4-bromo)cinnamoyl caudatin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.7%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	5.1.1. General procedure for the preparation of derivatives (6-10, 12-47) General procedure: A solution of 1 (0.2 mmol), DMAP (0.2 equiv), and the proper cinnamic acid (1.2 equiv) in anhydrous CH2Cl2 (8 mL) was added DCC (1.2 equiv) at 0 °C. The resulting mixture was stirred at room temperature until the starting material was not observed by TLC. The reaction mixture was filtered, and the residue was washed with CH2Cl2 (2 × 10 mL). The CH2Cl2 solution was washed with 5% HCl (3 × 30 mL), saturated NaHCO3 (3 × 30 mL) and saturated NaCl (3 × 30 mL), respectively. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. The residue was chromatographed using a silica gel column to yield the pure target compounds.

Reference： [1]Location in patent: experimental part Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Luo, Jie; Huang, Xiao-Yan; Chen, Hao; Zhou, Ning-Jia; Zhang, Xue-Mei; Chen, Ji-Jun [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 352 - 365]

25
[ 141-82-2 ]
[ 1122-91-4 ]
[ 1200-07-3 ]
[ 39773-47-2 ]

Reference： [1]Russian Journal of Organic Chemistry,2012,vol. 48,p. 860 - 863

26
[ 1200-07-3 ]
[ 67-63-0 ]
[ 1370259-82-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sulfuric acid for 48h; Reflux;	1 3-(4-Bromo-phenyl)-acrylic acid isopropyl ester (12) 3-(4-Bromo-phenyl)-acrylic acid isopropyl ester (12). To the solution of 4-bromocinnacid (1.135 g, 5 mmol) in isopropanol (50 mL) was added several drops of concentrated sulfuric acid. The mixture was heated to reflux for 48 hours. After cooled down, the residue was worked up with ethyl acetate. The ethyl acetate layer was washed with sat. NaHCC>3 aqueous solution, dried over Na2S04. After filtration and concentration, the resulting crude product was purified by silica column using hexane and ethyl acetate (from 100:1 to 75:1 then 50:1) as eluent to give 1.08 g white solid, in 80% yield. NMR (400 MHz, CDCI3): £7.59 (d, J = 16.0 Hz, 1H), 7.51 (d, J = 8.48 Hz, 2H), 7.38 (d, J= 8.44 Hz, 2H), 6.40 (d, J= 16.0 Hz, 1H), 5.14 (seq, J= 6.26 Hz, 1H), 1.31 (d, J= 6.24 Hz, 6H); 13C NMR (100 MHz, CDCI3): δ 166.38, 143.04, 133.63, 132.26, 129.53, 124.51, 119.70, 68.14, 22.07. mp 64-66 °C. IR v (Diamond, cm"1): 1703, 1637, 1304, 1172, 1104, 981, 817. MS (ESI) mlz found 268.9 (M + H)+, 271.1 (M + 2 + H)+ .

Reference： [1]Current Patent Assignee: VIRGINIA COMMONWEALTH UNIVERSITY - WO2013/106528, 2013, A1 Location in patent: Page/Page column 25; 26; 27; 35

27
[ 1200-07-3 ]
[ 68-35-9 ]
N-[4-(pyrimidin-2-yl-sulfamoyl)phenyl]4-bromocinnamamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;Reflux;	General procedure: A stirred solution of compound 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide (1 mmol) in CH2Cl2 (50 mL) wastreated with the appropriate substituted cinnamic acid,EDC·HCl (0.15 mmol), HOBt (0.05 mmol) and refluxedovernight. Then purification with recrystallization affordedthe corresponding compound as white powder.

Reference： [1]Letters in Organic Chemistry,2013,vol. 10,p. 374 - 379

28
[ 110-82-7 ]
[ 1200-07-3 ]
(E)-1-bromo-4-(2-cyclohexylvinyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With iron(III)-acetylacetonate; di-tert-butyl peroxide at 120℃; for 24h; Inert atmosphere; stereoselective reaction;	General procedure for the iron-catalyzed decarboxylativealkenylation of cycloalkanes General procedure: To a Schlenk tube equipped witha magnetic stir bar were added Fe(acac)3 (21.2 mg, 0.06 mmol)and cinnamic acid (0.3 mmol) under a nitrogen atmosphere.Cycloalkane (2.0 mL, 15-25 mmol) and DTBP (di-tert-butylperoxide, 0.6 mmol, 113 μL) were added under a nitrogenatmosphere and the resulting reaction mixture was stirred at 120°C for 24 h. After cooling to room temperature and removal ofvolatiles, the products were isolated by flash column chromatography(PE)
80%	With di-tert-butyl peroxide at 120℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Zhao, Jincan; Fang, Hong; Han, Jianlin; Pan, Yi [Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1718 - 1723]
[2]Ji, Jing; Liu, Ping; Sun, Peipei [Chemical Communications, 2015, vol. 51, # 35, p. 7546 - 7549]

29
[ 1200-07-3 ]
(E)-1-bromo-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With tert.-butylhydroperoxide; silver (II) carbonate; Langlois reagent; copper(l) chloride In water; 1,2-dichloro-ethane at 0 - 70℃; for 24h; stereoselective reaction;	Decarboxylative Trifluoromethylation of α,β-UnsaturatedAcids (Scheme 2); General Procedure General procedure: To a solution of substrate 1 (0.2 mmol, 1 equiv), CuCl (4 mg, 0.04mmol, 1 equiv), Ag2CO3 (33 mg, 0.12 mmol, 0.6 equiv), andNaSO2CF3 (93.6 mg, 0.6 mmol, 3.0 equiv) in DCE (2 mL) at 0 C,was slowly added TBHP (70% in water, 136 L, 1.0 mmol, 5.0equiv) with stirring. The reaction was allowed to warm to 70 C andthen stirred for 24 h. The resulting mixture was extracted withEtOAc (3 ~ 8 mL) and the combined organic layers were dried withNa2SO4 and then concentrated under vacuum. After evaporation,the residue was purified by column chromatography using silica gel(300.400 mesh; PE.EtOAc, 100:120:1).

Reference： [1]Yin, Jun; Li, Yaming; Zhang, Rong; Jin, Kun; Duan, Chunying [Synthesis, 2014, vol. 46, # 5, p. 607 - 612]

30
[ 127-19-5 ]
[ 1200-07-3 ]
[ 1632298-80-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tert.-butylhydroperoxide; nickel(II) acetate tetrahydrate In water at 100℃; for 16h;	Typical Procedure General procedure: To a mixture of cinnamic acid (0.148 g,1 mmol), Ni(OAc)2·4H2O (25 mg, 0.1 mmol), and N,Ndimethylacetamide(2 mL), tert-butyl hydroperoxide (0.39g, 3 mmol, 70% in water) was added at r.t. dropwise. Theresulting mixture was heated to 100 °C for 16 h, then themixture was added to dichloromethane (40 mL) and washedwith water and saturated brine. The organic solution wasdried with anhydrous magnesium sulfate and the desiredproduct was separated on a silica gel column (petroleumether-EtOAc).

Reference： [1]Zhang, Jia-Xiang; Wang, Yan-Jing; Wang, Nai-Xing; Zhang, Wei; Bai, Cui-Bing; Li, Yi-He; Wen, Jia-Long [Synlett, 2014, vol. 25, # 11, p. 1621 - 1625]

31
[ 1200-07-3 ]
[ 873-55-2 ]
[ 56361-12-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium iodide; copper(II) oxide In dimethyl sulfoxide at 100℃; for 24h; Sealed tube; Green chemistry; stereospecific reaction;
79%	With potassium carbonate In dimethyl sulfoxide at 100℃; for 10h; Green chemistry;
71%	With tetrabutylammonium perchlorate; acetic acid In water; acetonitrile at 20℃; for 2h; Electrolysis; regioselective reaction;

70%	With palladium diacetate; silver carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 75℃; for 6h; Inert atmosphere; Sealed tube;
65%	With manganese (II) acetate tetrahydrate In dimethyl sulfoxide at 110℃; for 12h;	1. General Procedure: General procedure: To a 25 ml round bottom flask were added cinnamic acid (0.5 mmol) , aromatic sulfinic acidsodium salt (1.5 mmol), Mn(OAc)2•4H2O(6.13 mg, 0.025 mmol) and DMSO (2ml). The round bottom flask was stirred under air at 110 °C for 12 h. The reaction mixture was cooled to roomtemperature and washed three times with saturated sodium chloride, extracted with EtOAc, andconcentrated in vacuo. The resulting residue was purified by flash column chromatography usinghexanes:EtOAc (8:1) as the eluent. All compounds are characterized by 1H NMR, 13C NMR,LRMS and their comparison to literature values

Reference： [1]Jiang, Qing; Xu, Bin; Jia, Jing; Zhao, An; Zhao, Yu-Rou; Li, Ying-Ying; He, Na-Na; Guo, Can-Cheng [Journal of Organic Chemistry, 2014, vol. 79, # 16, p. 7372 - 7379]
[2]Xu, Yanli; Tang, Xiaodong; Hu, Weigao; Wu, Wanqing; Jiang, Huanfeng [Green Chemistry, 2014, vol. 16, # 8, p. 3720 - 3723]
[3]Qian, Peng; Bi, Meixiang; Su, Jihu; Zha, Zhenggen; Wang, Zhiyong [Journal of Organic Chemistry, 2016, vol. 81, # 11, p. 4876 - 4882]
[4]Guo, Ruqing; Gui, Qingwen; Wang, Dadian; Tan, Ze [Catalysis Letters, 2014, vol. 144, # 8, p. 1377 - 1383]
[5]Xue, Na; Guo, Ruqing; Tu, Xinman; Luo, Weiping; Deng, Wei; Xiang, Jiannan [Synlett, 2016, vol. 27, # 19, p. 2695 - 2698]

32
[ 1200-07-3 ]
[ 824-79-3 ]
[ 56759-15-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With iodine; potassium carbonate In water at 60℃; for 10h; Green chemistry;
63%	With manganese (II) acetate tetrahydrate In dimethyl sulfoxide at 110℃; for 12h;	1. General Procedure: General procedure: To a 25 ml round bottom flask were added cinnamic acid (0.5 mmol) , aromatic sulfinic acidsodium salt (1.5 mmol), Mn(OAc)2•4H2O(6.13 mg, 0.025 mmol) and DMSO (2ml). The round bottom flask was stirred under air at 110 °C for 12 h. The reaction mixture was cooled to roomtemperature and washed three times with saturated sodium chloride, extracted with EtOAc, andconcentrated in vacuo. The resulting residue was purified by flash column chromatography usinghexanes:EtOAc (8:1) as the eluent. All compounds are characterized by 1H NMR, 13C NMR,LRMS and their comparison to literature values
50%	With palladium diacetate; silver carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 75℃; for 6h; Inert atmosphere; Sealed tube;

Reference： [1]Gao, Jian; Lai, Junyi; Yuan, Gaoqing [RSC Advances, 2015, vol. 5, # 82, p. 66723 - 66726]
[2]Xue, Na; Guo, Ruqing; Tu, Xinman; Luo, Weiping; Deng, Wei; Xiang, Jiannan [Synlett, 2016, vol. 27, # 19, p. 2695 - 2698]
[3]Guo, Ruqing; Gui, Qingwen; Wang, Dadian; Tan, Ze [Catalysis Letters, 2014, vol. 144, # 8, p. 1377 - 1383]

33
[ 1200-07-3 ]
[ 1572-10-7 ]
(E)-3-(4-bromophenyl)-N-(5-phenyl-1H-pyrazol-3-yl)acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 1h; Reflux;	14 4.4. General procedure for the synthesis of 5-phenyl-1H-pyrazolderivatives (5a-5x) General procedure: Compounds 5a-5x were synthesized by coupling substituted 3a-3c with cinnamic acids, using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCl) and N-hydroxybenzotriazole (HOBt) as condensing agent. The mixture was refluxed in anhydrous CH2Cl2 for 1-3 h. The products were extracted with ethyl acetate. The extract was washed successively with 5% HCl, then evaporated and purified by column chromatography over silica gel to give the compound.

Reference： [1]Wang, Shu-Fu; Yin, Yong; Zhang, Ya-Liang; Mi, Shan-Wei; Zhao, Meng-Yue; Lv, Peng-Cheng; Wang, Bao-Zhong; Zhu, Hai-Liang [European Journal of Medicinal Chemistry, 2015, vol. 93, p. 291 - 299]

34
[ 1200-07-3 ]
[ 78583-82-1 ]
(E)-3-(4-bromophenyl)-N-(5-(4-bromophenyl)-1H-pyrazol-3-yl)acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 1h; Reflux;	22 4.4. General procedure for the synthesis of 5-phenyl-1H-pyrazolderivatives (5a-5x) General procedure: Compounds 5a-5x were synthesized by coupling substituted 3a-3c with cinnamic acids, using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCl) and N-hydroxybenzotriazole (HOBt) as condensing agent. The mixture was refluxed in anhydrous CH2Cl2 for 1-3 h. The products were extracted with ethyl acetate. The extract was washed successively with 5% HCl, then evaporated and purified by column chromatography over silica gel to give the compound.

Reference： [1]Wang, Shu-Fu; Yin, Yong; Zhang, Ya-Liang; Mi, Shan-Wei; Zhao, Meng-Yue; Lv, Peng-Cheng; Wang, Bao-Zhong; Zhu, Hai-Liang [European Journal of Medicinal Chemistry, 2015, vol. 93, p. 291 - 299]

35
[ 1200-07-3 ]
[ 78597-54-3 ]
(E)-3-(4-bromophenyl)-N-(5-(p-tolyl)-1H-pyrazol-3-yl)acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 1h; Reflux;	12 4.4. General procedure for the synthesis of 5-phenyl-1H-pyrazolderivatives (5a-5x) General procedure: Compounds 5a-5x were synthesized by coupling substituted 3a-3c with cinnamic acids, using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCl) and N-hydroxybenzotriazole (HOBt) as condensing agent. The mixture was refluxed in anhydrous CH2Cl2 for 1-3 h. The products were extracted with ethyl acetate. The extract was washed successively with 5% HCl, then evaporated and purified by column chromatography over silica gel to give the compound.

Reference： [1]Wang, Shu-Fu; Yin, Yong; Zhang, Ya-Liang; Mi, Shan-Wei; Zhao, Meng-Yue; Lv, Peng-Cheng; Wang, Bao-Zhong; Zhu, Hai-Liang [European Journal of Medicinal Chemistry, 2015, vol. 93, p. 291 - 299]

36
[ 896464-16-7 ]
[ 1200-07-3 ]
(E)-tert-butyl 2-(3-(4-bromophenyl)acryloyl)-2,7-diazaspiro[3.5]nonane-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example Al: Preparation of tert-butyl (E)-2-(3-(4-bromophenyl)acryloyl)-2,7- diazaspiro[3.5]nonane-7-carboxylate (General Procedure A) [00230] 4-Bromocinnamic acid (1.1 g, 4.86 mmol) was dissolved in 10 mL of DMF and after the addition of EDC (1.1 g, 5.75 mmol) and HOBT (0.9 g, 5.75 mmol), the mixture was stirred at room temperature for 30 minutes. DIPEA (3.8 ml, 22.1 mmol) and tert-butyl 2,7- diazaspiro[3,5]nonane-7-carboxylate (1 g, 4.42 mmol) were added to the resulting mixture and the reaction mixture was stirred for 17 hours at room temperature. When the reaction was determined to be complete by HPLC, the reaction mixture was concentrated under reduced pressure and the resulting solid was dissolved in EtOAc. The solution was washed with saturated aqueous NaHC03, washed with citric acid and dried over Na2S04. The resulting organic layer was concentrated under reduced pressure afforded tert-butyl-(E)-2-(3-(4-bromophenyl)acryloyl)- 2,7-diazaspiro[3.5]nonane-7-carboxylate as a white solid which was used directly into the next step without purification. MS (EI) m/z 436 [(M+H)+].

Reference： [1]Patent: WO2015/48567,2015,A1 .Location in patent: Paragraph 00230

37
[ 1200-07-3 ]
[ 62129-39-9 ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 5410 - 5413

38
[ 1200-07-3 ]
[ 24250-84-8 ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 5410 - 5413
[2]Journal of the American Chemical Society,2015,vol. 137,p. 12977 - 12983

39
[ 24424-99-5 ]
[ 1200-07-3 ]
[ 4248-19-5 ]
[ 62129-39-9 ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 5410 - 5413

40
[ 1200-07-3 ]
[ 541-41-3 ]
C₁₂H₁₁BrO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at -7℃; for 0.5h;	General procedure for the synthesis of intermediates 3a-3l General procedure: To a 250 mL round-bottom flask containing 10 mmol of substitutedcinnamic acid (2a-2l), 30 mL of dry THF and 19.9 mmol triethylamineat 7 C, 10 mmol of ethyl chloroformate was addeddropwise. After being stirred for an additional 30 min at the sametemperature, the mixture was filtered with suction and cake waswashed with THF. The reaction mixture was allowed to warm to10 C and 2.7 g (30 mmol) of anhydrous sodium borohydride wasadded in one portion. To this suspension, 15 mL of absolute methanolwas added dropwise over 1 h at the same temperature. Afterbeing stirred at room temperature for additional 1 h, the reactionmixture was poured into water and extracted with dichloromethane.The combined organic layer were dried over anhydrousNa2SO4 and concentrated. The residue obtained was purified bycolumn chromatography using hexane/ethyl acetate (60/40) aseluent to afford the pure compounds 3a-3l (overall yield 60-75%) and were further identified through ESI-MS and NMR

Reference： [1]Manral, Apra; Saini, Vikas; Meena, Poonam; Tiwari, Manisha [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6389 - 6403]

41
[ 1200-07-3 ]
[ 3156-37-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With trichloroisocyanuric acid; N,N-dimethyl-formamide; sodium nitrite for 8.5h; Reflux;	Conventional Procedure for Synthesis of Nitro Compounds Using TCICA/DMF Reagent General procedure: To 0.01 mol phenol (as a typical example for aromatic compounds), about 0.01 mol of TCICA/DMF reagent and sodium nitrite (1g) were added with CH2Cl2 or acetonitrile (25mL) in a previously cleaned round-bottom flask and stirred under reflux condition about 8 to 10 h. The completion of there action was checked by TLC. After completion there action mixture was washed with NaHCO3 solution and then treated with ethylacetate. The organic layer was separated, dried over anhydrous MgSO4, evaporated under vacuum, and purified with column chromatography using ethylacetate-hexane as eluent to get pure product 4-nitrophenol as yellow powder

Reference： [1]Kumar, Mukka Satish; Rajanna, Kamatala Chinna; Venkateswarlu, Marri; Venkanna, Purugula; Saiprakash, Pondichery Kuppuswamy [Synthetic Communications, 2015, vol. 45, # 19, p. 2251 - 2258]

42
[ 3240-34-4 ]
[ 1200-07-3 ]
2-(4-bromophenyl)-2-oxoethane-1,1-diyl diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sulfuric acid In 1,2-dichloro-ethane at 20℃; Reflux;	α-Keto Diacetates 2; General Procedure General procedure: α-Keto Diacetates 2; General ProcedureTo a solution of a cinnamic acid 1 (0.4 mmol) and PIDA (1.2 mmol) inDCE (8 mL) was added concd H2SO4 (0.4 mmol) at r.t. under vigorousstirring. The resulting mixture was then heated to reflux and monitoredby TLC. Upon reaction completion, the mixture was cooled tor.t., poured into a sat. aq solution of NaHCO3 (50 mL) and extractedwith CH2Cl2 (3 × 40 mL). The combined organic layer was washedwith brine (100 mL) and dried over anhydrous Na2SO4. Evaporation ofthe solvent under reduced pressure and purification of the crude residueby flash column chromatography on silica gel (EtOAc-PE) gavethe desired product 2. For substrates 1b and 1c, the reactions werecarried out at -30 °C for 1 h, and then warmed to r.t. For substrates1h-j, BF3·OEt2 (1.0 equiv) was added after the addition of H2SO4.

Reference： [1]Liu, Le; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang [Synthesis, 2015, vol. 47, # 19, p. 2924 - 2930]

43
[ 2589-57-3 ]
[ 1200-07-3 ]
(E)-methyl 4-(4-bromophenyl)-2,2-dimethylbut-3-enoate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4968 - 4971

44
[ 1200-07-3 ]
[ 6638-79-5 ]
[ 652978-38-6 ]

Yield	Reaction Conditions	Operation in experiment
26.8 g	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 20℃; for 16h;	1.1 Step 1: 3-(4-bromo-phenyl)-N-methoxy-N-methyl-acrylamide 4-Bromocinnamic acid (28.3 g, 124.6 mmol), N,O-dimethylhydroxylamine hydrochloride (14.6 g, 149.6 mmol), HOBT (33.7 g, 249.3 mmol), EDAC (47.8 g, 249.3 mmol) and triethylamine (34.7 mL, 249.3 mmol) were added to dichloromethane (800.0 mL). The reaction mixture was stirred at room temperature for 16 hours, quenched with a saturated solution of ammonium chloride, and then extracted with dichloromethane three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to give 26.8 g of the titled compound as a white solid. (0124) 1H NMR (400 MHz, CDCl3) 7.66 (d, 1H), 7.51 (d, 2H), 7.43 (d, 2H), 7.02 (d, 1H), 3.77 (s, 3H), 3.31 (s, 3H)
	With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 20℃;

Reference： [1]Current Patent Assignee: YUHAN CORPORATION - US2015/291563, 2015, A1 Location in patent: Paragraph 0123; 0124
[2]Maeta, Naoya; Kamiya, Hidehiro; Okada, Yohei [Journal of Organic Chemistry, 2020, vol. 85, # 10, p. 6551 - 6566]

45
[ 109-99-9 ]
[ 1200-07-3 ]
[ 1201224-41-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With tris(bipyridine)ruthenium(II) dichloride hexahydrate; dibenzoyl peroxide In acetonitrile at 20℃; Irradiation; Inert atmosphere;	2-Arylvinyl Ethers 3; General Procedure General procedure: Ru(bpy)3Cl2·6H2O (2 mol%, 6 mg), cinnamic acid derivative 1 (1equiv, 0.5 mmol), benzoyl peroxide (2.8 equiv, 1.4 mmol), anhyd ether 2 (3 mL), and anhyd MeCN (3 mL) were added to a 10 mL reaction vessel equipped with a magnetic stirrer bar. The mixture was irradiated with a 46 W CFL at r.t. for 4-6 h. The yield was determined by isolation of the product using flash chromatography.

Reference： [1]Liu, Zheng; Wang, Leifeng; Liu, Dong; Wang, Zhigang [Synlett, 2015, vol. 26, # 20, p. 2849 - 2852]

46
[ 2941-78-8 ]
[ 1200-07-3 ]
N-(4-bromocinnamoyl)-5-methylanthranilic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pDRf₁-(4-coumaroyl:CoA ligase 5 from Arabidopsis thaliana)-(hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/benzoyltransferase 1 from Dianthus caryophyllus) recombinant yeast In dimethyl sulfoxide at 30℃; for 24h;	Production of cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates General procedure: An overnight culture from a single colony of the pDRf1-4CL5-HCBT1 recombinant yeast grown on 2X YNB medium without amino acids, supplemented with 6% glucose and 2X CSM-Ura, was used to inoculated 4 mL of fresh minimal medium at an OD600 = 0.15 and shaken at 200 rpm at 30°C. All precursors were prepared in DMSO and added 5 hours post inoculation at the concentrations indicated in S1, S2 and S3 Tables. The anthranilate acceptors were added to the medium at a final concentration of 300 μM (for anthranilate, 3-hydroxyanthranilate, 3-methylanthranilate, and 5-nitroanthranilate) or 50 μM (for 3-chloroanthranilate, 5-methylanthranilate, 3-methoxyanthranilate, 5-fluoroanthranilate, 5-iodoanthranilate, and 5-chloroanthranilate). These concentrations were selected to limit toxicity and growth inhibition due to either the supplied precursors or the metabolites produced. The cultures were shaken at 200 rpm at 30°C for 24 h in the presence of the precursors for the production of cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates. Yeast colonies harboring the pDRf1-HCBT1 or pDRf1-4CL5 control vectors were grown under similar conditions. For the detection of metabolites, an aliquot of the culture medium was collected and cleared by centrifugation (21,000xg for 5 min at 4°C), mixed with an equal volume of cold methanol:water (1:1, v/v), and filtered using Amicon Ultra centrifugal filters (3,000 Da MW cutoff regenerated cellulose membrane; Millipore, Billerica, MA) prior to LC-TOF MS analysis. The separation and identification of the metabolites were performed using high-performance liquid chromatography (HPLC), electrospray ionization (ESI), and time-of-flight (TOF) mass spectrometry (MS) as previously described [35]. For each compound, the measured masses agreed with the expected theoretical masses within less than 5 ppm mass error. Standard solutions of DHavnD and dianthramide B were prepared in methanol:water (1:1, v/v). Values obtained for the production of DHavnD and dianthramide B are the average of four replicates (n = 4). ESI-MS spectra of other cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates were obtained from single feeding experiments for each combination of precursors.

Reference： [1]Eudes, Aymerick; Benites, Veronica Teixeira; Wang, George; Baidoo, Edward E.K.; Lee, Taek Soon; Keasling, Jay D.; Loqué, Dominique [PLoS ONE, 2015, vol. 10, # 10]

47
[ 1200-07-3 ]
[ 778641-02-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N,N-dimethyl-formamide; potassium bromide; trichlorophosphate In acetonitrile at 20℃; Sonication;	Ultrasonically Assisted Vilsmeier-Haack Synthesis ofb-Bromostyrenes (Sonication) General procedure: To a centimolar cinnamic acid, 0.015 mol of Vilsmeier-Haackreagent and KBr and solvent (Me CN) were added in a cleanin a round bottom flask and clamped in a sonicator at roomtemperature. After completion of the reaction, as ascertainedby TLC, the reaction mixture is treated with sodium thiosulfate solution, followed by the addition of ethyl acetate. Theseparation and purification procedure is by and large similarto the above procedure.
	With N-Bromosuccinimide; manganese (II) acetate tetrahydrate In water; acetonitrile at 20℃;

Reference： [1]Kumar, M. Satish; Rajanna; Venkanna; Venkateswarlu; Sudhakar Chary [Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2016, vol. 46, # 5, p. 642 - 646]
[2]Cai, Guilong; Zhou, Zhibing; Wu, Wenchao; Yao, Bo; Zhang, Shaowen; Li, Xiaofang [Organic and Biomolecular Chemistry, 2016, vol. 14, # 37, p. 8702 - 8706]

48
[ 1200-07-3 ]
[ 6142-65-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2498 - 2503

49
[ 1200-07-3 ]
[ 80793-25-5 ]

Reference： [1]Chinese Chemical Letters,2016,vol. 27,p. 555 - 558

50
[ 1200-07-3 ]
[ 304-20-1 ]
E-3-(4-bromostyryl)[1,2,4]triazolo[3,4-a]phthalazine [ No CAS ]

Reference： [1]ChemMedChem,2016,vol. 11,p. 1078 - 1089

51
[ 1200-07-3 ]
[ 108-67-8 ]
C₁₇H₁₇Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tert.-butylhydroperoxide In water at 110℃; for 4h; Sealed tube;	Activity test General procedure: The typical experimental procedure for the decarboxylative coupling reaction was as follows: Cu-X catalyst (5mg), CA 1 (0.5mmol), TBHP (1.0mmol, 70% aqueous solution), and ethanol 2 (2.0mL) were placed in a sealed tube (10mL). The reaction was heated at 110°C for 4h. After the reaction finished, the catalyst was separated by centrifugation and filtration to obtain the liquid phase. The liquid products were analyzed by an Agilent 1260 Infinity Liquid Chromatogram. The pure product was obtained by flash column chromatography on silica gel using petroleum ether (60-90°C) and ethyl acetate as eluents. Compounds described in the literature were characterized by comparing their 1H and 13C NMR spectra and MS data with the reported data. The 1H NMR (500 and 400MHz) and 13C NMR (125 and 100MHz) were recorded with spectrometers at 20°C using CDCl3 as the solvent. Chemical shifts are given in parts per million relative to TMS as the internal standard at room temperature

Reference： [1]Chen, Shengchun; Shao, Zhen; Fang, Zhongxue; Chen, Qun; Tang, Ting; Fu, Wenqian; Zhang, Lei; Tang, Tiandi [Journal of Catalysis, 2016, vol. 338, p. 38 - 46]

52
[ 64-17-5 ]
[ 1200-07-3 ]
[ 875852-27-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tert.-butylhydroperoxide In water at 110℃; for 4h; Sealed tube;	Activity test General procedure: The typical experimental procedure for the decarboxylative coupling reaction was as follows: Cu-X catalyst (5mg), CA 1 (0.5mmol), TBHP (1.0mmol, 70% aqueous solution), and ethanol 2 (2.0mL) were placed in a sealed tube (10mL). The reaction was heated at 110°C for 4h. After the reaction finished, the catalyst was separated by centrifugation and filtration to obtain the liquid phase. The liquid products were analyzed by an Agilent 1260 Infinity Liquid Chromatogram. The pure product was obtained by flash column chromatography on silica gel using petroleum ether (60-90°C) and ethyl acetate as eluents. Compounds described in the literature were characterized by comparing their 1H and 13C NMR spectra and MS data with the reported data. The 1H NMR (500 and 400MHz) and 13C NMR (125 and 100MHz) were recorded with spectrometers at 20°C using CDCl3 as the solvent. Chemical shifts are given in parts per million relative to TMS as the internal standard at room temperature

Reference： [1]Chen, Shengchun; Shao, Zhen; Fang, Zhongxue; Chen, Qun; Tang, Ting; Fu, Wenqian; Zhang, Lei; Tang, Tiandi [Journal of Catalysis, 2016, vol. 338, p. 38 - 46]

53
[ 1200-07-3 ]
[ 80-17-1 ]
[ 56361-12-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With Eosin Y; oxygen; caesium carbonate; potassium iodide In water; N,N-dimethyl-formamide at 20℃; Irradiation;

Reference： [1]Cai, Shunyou; Xu, Yaohui; Chen, Danling; Li, Lihuang; Chen, Qifa; Huang, Mingqiang; Weng, Wen [Organic Letters, 2016, vol. 18, # 12, p. 2990 - 2993]

54
[ 39773-47-2 ]
[ 479074-63-0 ]
[ 1200-07-3 ]
[ 24250-84-8 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 56412 - 56420
[2]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1570 - 1576

55
decursinol [ No CAS ]
[ 1200-07-3 ]
(7S)-(+)-3-(4-bromophenyl)acrylic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.2%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	General procedure for the synthesis of cinnamoyl-, haro-cinnamoyl-, NO2-cinnamoyl- and (OCH3)ncinnamoyl-decursin derivatives (5a-e, 6a-i) General procedure: The mixture of cinnamic acid (1.2 equiv), EDC (2 equiv) and 4-DMAP (0.4 equiv) was dissolved inanhydrous dichloromethane. After (+)-Decursinol (1 equiv) was added, the reaction mixture stirred to roomtemperature for 5-12 hours. The completion of reaction was juged by TLC. When a spot of (+)-decursinolwas disappeared on TLC, the reaction was finished. The mixture was concentrated in vacuo and the residuewas purified by flash silica gel column chromatography using EtOAc/Hexane system as eluent.

Reference： [1]Lee, Jee-Hyun; Kim, Min-Ah; Park, Seoyoung; Cho, Soo-Hyun; Yun, Eunju; O, Yu-Seok; Kim, Jiseon; Goo, Ja-Il; Yun, Mi-Young; Choi, Yongseok; Oh, Sangtaek; Song, Gyu-Yong [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3529 - 3532]

56
[ 2033-24-1 ]
[ 1122-91-4 ]
[ 1200-07-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With carrot juice In water at 20℃; for 0.25h; Sonication; Green chemistry;	Coumarin-3-carboxylic andcinnamic acids synthesis. General procedure General procedure: 2-Hydroxybenzaldehyde (acetophenone, or benzaldehydes) (1.0 mmol) and Meldrum’s acid (1.01 mmol) were suspended in the aqueous medium (juice or waste water) (2 mL). The resulting mixture was subjected to ultrasound irradiation at room temperature for 5 min (15 min). The precipitate so formed was filtrated under vacuum. Structural assignments (NMR) was made by comparison of the recorded analytical data with those of commercially available sample or those already reported for the same compounds.2-6 The aqueous medium (juice or waste water) was recovered by filtration and re-used as such to perform further processes.

Reference： [1]Fiorito, Serena; Taddeo, Vito Alessandro; Genovese, Salvatore; Epifano, Francesco [Tetrahedron Letters, 2016, vol. 57, # 43, p. 4795 - 4798]

57
[ 1200-07-3 ]
[ 586410-15-3 ]
(E)-3-(4-bromophenyl)-N-(4-(3,5-dimethoxystyryl)phenyl)acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 0.5h;	General procedure for the preparation of compounds 7a-7o General procedure: A solution of the appropriate caffic acid derivitives (1mmol), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo [4,5-b]pyridinium 3-oxid hexafl-uorophosphate (HATU) (1.2mmol) and N,N-diisopropylethylamine (2mmol) in dichloromethane was stirred at ambient temperature for 30min. Compound 4 (1mmol) was added to the solution, and stirred overnight. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with diluted hydrochloric acid, saturated sodium bicarbonate solution and brine. And dried with anhydrous magnesium sulfate, and the solvent was evaporated in vacuum to give the crude product, which was purified by chromatography on silica gel.

Reference： [1]Li, Shanshan; Zhang, Wenda; Yang, Yanwei; Ma, Ting; Guo, Jianpeng; Wang, Shanshan; Yu, Wenying; Kong, Lingyi [European Journal of Medicinal Chemistry, 2016, vol. 124, p. 1006 - 1018]

58
[ 24250-84-8 ]
[ 1200-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	With phenylalanine ammonia lyase from Rhodotorula graminis; In aq. buffer; for 1h;pH 8.8;Enzymatic reaction;	General procedure: Substrate solutions of 4-bromo, 3-bromo, 4-fluoro, 3-fluoro and 3-nitro phenylalanine were made, 20mM substrate in 100mM Tris buffer pH 8.8. The screening was set up in a UV-Star Microplates (96 well, F-bottom, Greiner Bio-one) and each well contained the following: 140muL Tris buffer 100mM, pH 8.8, 10muL of purified enzyme, 50muL phenylalanine solution. Absorbance was measured using a plate reader at 290nm for 1h with intervals of 43s and hits were identified by an increase in the absorbance.

Reference： [1]Tetrahedron,2016,vol. 72,p. 7343 - 7347

59
[ 1200-07-3 ]
[ 24250-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	With phenylalanine ammonia lyase from Rhodotorula graminis; ammonium carbamate; In aq. buffer; at 30℃;pH 9.0;Kinetics;	General procedure: Solutions of the substrates under investigation were made up in 0.5M ammonium carbamate/1M Tris, pH 9.0 and dilutions were made with the following concentrations: 3, 2, 1, 0.5, 0.2, 0.02, 0.002 and 0mM of cinnamic acid. Scopoletin solution - 288.25mg of scopoletin was dissolved in 50mL dH2O to make a stock solution. This stock solution was then diluted 1/5 to create a working solution that had a fluorescence of approximately 30,000 RFU. The screening was set up in a 96-well plate and each well contained the following: 100muL substrate solution, 10muL HRP (1mg/mL in dH2O), 10muL l-AAO (1 in 10 dilution of stock in dH2O), 40muL scopoletin solution, 40muL purified PAL. Kinetic data was measured on a plate reader at 30C. Excitation wavelength 360nm; emission wavelength 480nm; 15s interval.

Reference： [1]Tetrahedron,2016,vol. 72,p. 7343 - 7347
[2]Tetrahedron,2016,vol. 72,p. 7256 - 7262

60
[ 1200-07-3 ]
[ 35661-39-3 ]
[ 71989-26-9 ]
[ 76-05-1 ]
[ 292150-20-0 ]
C₂₃H₃₂BrN₅O₆*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1219 - 1224

61
[ 109-99-9 ]
[ 1200-07-3 ]
1-(4-bromophenyl)-2-(tetrahydrofuran-2-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With dipotassium peroxodisulfate In tetrahydrofuran at 100℃; for 12h; Schlenk technique; Sealed tube;
80%	With dipotassium peroxodisulfate at 100℃; for 12h;	4 Example 4 General procedure: To a 20 mL reaction tube was added α, β-unsaturated carboxylic acid (0.2 mmol), K2S2O8 (0.4 mmol) and tetrahydrofuran (1.5 mL).The reaction mixture was stirred at 100 ° C for 12 hours.After the reaction was completed, the resulting mixture was diluted with ethyl acetate and washed with an equal amount of saturated NaHCO 3 solution, then the organic phase was separated and washed with water and the aqueous phase was extracted three times with ethyl acetate.The combined organic extracts were dried over anhydrous sodium sulfate and filtered. The resulting product was concentrated in vacuo and purified by silica gel column chromatography (hexane / ethyl acetate = 15) to give the desired product.
80%	With dipotassium peroxodisulfate at 100℃; for 12h;	4 Example 4 General procedure: Cinnamic acid derivatives (0.2 mmol), K2S2O8 (0.4 mmol), and tetrahydrofuran (1.5 mL) were added to a 20 mL reaction tube.The reaction mixture was stirred at 100 ° C for 12 hours.After the reaction was completed, the resulting mixture was diluted with ethyl acetate and washed with an equal amount of saturated NaHCO 3 solution, then the organic phase was separated and washed with water and the aqueous phase was extracted three times with ethyl acetate.The combined organic extracts were dried over anhydrous sodium sulfate and filtered.The resulting product was concentrated in vacuo and purified by silica gel column chromatography (hexane / ethyl acetate = 15) to give the desired product.

Reference： [1]Ji, Peng-Yi; Liu, Yu-Feng; Xu, Jing-Wen; Luo, Wei-Ping; Liu, Qiang; Guo, Can-Cheng [Journal of Organic Chemistry, 2017, vol. 82, # 6, p. 2965 - 2971]
[2]Current Patent Assignee: YUANJIANG HUALONG CATALYST TECH - CN106366054, 2017, A Location in patent: Paragraph 0070; 0089; 0090; 0091; 0092
[3]Current Patent Assignee: YUANJIANG HUALONG CATALYST TECH - CN106349194, 2017, A Location in patent: Paragraph 0069; 0088; 0089; 0090; 0091

62
[ 1200-07-3 ]
[ 762-04-9 ]
[ 18276-83-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With copper(ll) sulfate pentahydrate; oxygen In acetonitrile at 60℃; for 6h;	3.20 4.2 General procedure for the synthesis of β-ketophos-phonates General procedure: Starting from the alkenyl acids: alkenyl acids 1 (0.2mmol), H-phosphonates 2 (0.4mmol), and CuSO4·5H2O (10mol%) were dissolved in 4mL CH3CN at round-bottomed flask and stirred at 60°C for 6h in an air atmosphere. Starting from the alkenes: alkenes 4 (0.2mmol), H-phosphonates 2 (0.3mmol), and CuSO4·5H2O (10mol%) were dissolved in 4mL CH3CN at round-bottomed flask and stirred at 60°C for 3h in an air atmosphere. Then, CH3CN was evaporated, and the reaction mixture was quenched with water, followed by extraction with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. The crude product was purified by silica gel chromatography (petroleum ether: ethyl acetate=1:1) to give the desired product.

Reference： [1]Chen, Xi; Chen, Xiaolan; Li, Xu; Qu, Chen; Qu, Lingbo; Bi, Wenzhu; Sun, Kai; Zhao, Yufen [Tetrahedron, 2017, vol. 73, # 17, p. 2439 - 2446]

63
[ 1122-91-4 ]
[ 479074-63-0 ]
[ 1200-07-3 ]
[ 24250-84-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1570 - 1576

64
[ 1200-07-3 ]
(S)-4-(2-hydroxyethyl)-3-methylenedihydrofuran-2(3H)-one [ No CAS ]
C₁₆H₁₅BrO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.9%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	3 Compound 6s - 4: white solid; compound at room temperature 3s (35.5 mg, 0 . 5mmol) with to bromine cinnamic acid (1.2eq) is dissolved in methylene chloride, added EDCI (1.2eq) and DMAP (0.02eq), two hours reaction time, the reaction solution washing, dichloromethane extraction, the combined organic phase, drying and condensing column to obtain the product 62.0g, yield 70.9%.

Reference： [1]Current Patent Assignee: SECOND MILITARY MEDICAL UNIVERSITY - CN104926761, 2017, B Location in patent: Paragraph 0290; 0291; 0292; 0293; 0294

65
[ 1200-07-3 ]
2′-O-acetyl-11-O-(aminoethyl)carbamoyl-3-O-descladinosyl-3-oxo-clarithromycin [ No CAS ]
C₄₄H₆₆BrN₃O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-(4-bromophenyl)acrylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 6h; Stage #2: 2′-O-acetyl-11-O-(aminoethyl)carbamoyl-3-O-descladinosyl-3-oxo-clarithromycin In tetrahydrofuran at 20℃; for 4h;	1.7. General methods for 11-O-aralkylcarbamoyl-3-O-descladinosyl-3-oxo-clarithromycin derivatives (7-30) General procedure: To a solution of benzoic acid (61 mg, 0. 50 mmol) and HOBt (85 mg, 0.63 mmol) in THF (4.0 mL) at 0°C was added dropwise DCC (130 mg, 0.63 mmol) in THF (2.0 mL). The resulting solution was allowed to stir at 0 °C for 6 h and then added compound 6 (300 mg, 0.42 mmol). The reaction mixture was stirred for 4 h at room temperature and evaporated in vacuum to dryness. The residue was filtered and then dissolved in ethyl acetate (15 mL).The resulting solution was washed by saturated NaHCO3 solution and brine. The organic layers was combined and dried over anhydrous Na2SO4, filtered, and concentrated in vacuum to afford crude product. The above crude product was dissolved in methanol, and stirred for 24 h at 55 °C. The reaction solution was subsequent concentrated to provide the crude product. The above crude product was purified by flash column chromatography (dichloromethane/methanol, 30:1) to afford the desired product 7 (260 mg, 80%). According to the above procedure, corresponding compounds 8-30 were prepared in yields ranging from 47% to 90%.

Reference： [1]Jia, Li; Yan, Mi; Shen, Yan; Qin, Yinhui; Qiang, Shengsheng; Ma, Shutao [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3693 - 3697]

66
[ 1200-07-3 ]
[ 71-91-0 ]
[ 24393-53-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	With urea; at 140℃; for 2h;Green chemistry;	General procedure: A 10-mL test-tube was equipped with magnetic stirring bar and charged with 1 mmol cinnamic acid and 6 mL DES, heated at 140 C in a preheated oil bath for 2 hours, then the mixture was cooled to room temperature, extracted with ethyl acetate (3*15 mL), combined and evaporated under vacuum. Pure product was obtained by silica gel column chromatography with petroleum ether and ethyl acetate. All the compounds, after purification, were weighted and characterized by MS, 1H NMR, 13C NMR, and then compared them with the spectral data of authentic samples.

Reference： [1]Synthetic Communications,2018,vol. 48,p. 68 - 75

67
[ 1200-07-3 ]
benzyldimethyl-2-hydroxyethyl-ammonium chloride [ No CAS ]
benzyl 4-bromocinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With urea at 140℃; for 2h; Green chemistry;	Typical Procedure for the esterification of carboxylic acid in DES General procedure: A 10-mL test-tube was equipped with magnetic stirring bar and charged with 1 mmol cinnamic acid and 6 mL DES, heated at 140 °C in a preheated oil bath for 2 hours, then the mixture was cooled to room temperature, extracted with ethyl acetate (3*15 mL), combined and evaporated under vacuum. Pure product was obtained by silica gel column chromatography with petroleum ether and ethyl acetate. All the compounds, after purification, were weighted and characterized by MS, 1H NMR, 13C NMR, and then compared them with the spectral data of authentic samples.

Reference： [1]Yasmin, Sumera; Sheng, Wen-Bing; Peng, Cai-Yun; Rahman, Atta-ur; Liao, Duan-Fang; Choudhary, M. Iqbal; Wanga, Wei [Synthetic Communications, 2018, vol. 48, # 1, p. 68 - 75]

68
[ 1200-07-3 ]
[ 1112-67-0 ]
n-butyl 4-bromocinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With 1H-imidazole at 140℃; for 2h; Green chemistry;	Typical Procedure for the esterification of carboxylic acid in DES General procedure: A 10-mL test-tube was equipped with magnetic stirring bar and charged with 1 mmol cinnamic acid and 6 mL DES, heated at 140 °C in a preheated oil bath for 2 hours, then the mixture was cooled to room temperature, extracted with ethyl acetate (3*15 mL), combined and evaporated under vacuum. Pure product was obtained by silica gel column chromatography with petroleum ether and ethyl acetate. All the compounds, after purification, were weighted and characterized by MS, 1H NMR, 13C NMR, and then compared them with the spectral data of authentic samples.

Reference： [1]Yasmin, Sumera; Sheng, Wen-Bing; Peng, Cai-Yun; Rahman, Atta-ur; Liao, Duan-Fang; Choudhary, M. Iqbal; Wanga, Wei [Synthetic Communications, 2018, vol. 48, # 1, p. 68 - 75]

69
[ 1200-07-3 ]
[ 67-48-1 ]
methyl 4-bromocinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With urea at 140℃; for 2h; Green chemistry;	Typical Procedure for the esterification of carboxylic acid in DES General procedure: A 10-mL test-tube was equipped with magnetic stirring bar and charged with 1 mmol cinnamic acid and 6 mL DES, heated at 140 °C in a preheated oil bath for 2 hours, then the mixture was cooled to room temperature, extracted with ethyl acetate (3*15 mL), combined and evaporated under vacuum. Pure product was obtained by silica gel column chromatography with petroleum ether and ethyl acetate. All the compounds, after purification, were weighted and characterized by MS, 1H NMR, 13C NMR, and then compared them with the spectral data of authentic samples.

Reference： [1]Yasmin, Sumera; Sheng, Wen-Bing; Peng, Cai-Yun; Rahman, Atta-ur; Liao, Duan-Fang; Choudhary, M. Iqbal; Wanga, Wei [Synthetic Communications, 2018, vol. 48, # 1, p. 68 - 75]

70
[ 60-29-7 ]
[ 1200-07-3 ]
C₁₂H₁₅BrO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With tert.-butylhydroperoxide; copper; sodium carbonate at 80℃; for 17h; Sealed tube;	2.2 General procedure General procedure: Taking the synthesis of (E)-1-(3-ethoxybut-1-enyl)-4-methylbenzene (3a) as an example. Copper powder(0.03 mmol), Na2CO3 (0.03 mmol), tert-butyl hydroperoxide(0.9 mmol, 70% in water) was added successively into amixture of 4-methylcinnamic acid (0.3 mmol) and ethyl ether(3 mL) at room temperature in sealed tube. The mixturereacted at 80 °C for 17 h. After the reaction was completed,the resulting mixture was concentrated by a rotary evaporatorand then separated by column chromatography on silica gelby using petroleum ether and ethyl acetate as eluent.

Reference： [1]Zhang, Tong; Lan, Xing-Wang; Zhou, Yu-Qiang; Wang, Nai-Xing; Wu, Yue-Hua; Xing, Yalan; Wen, Jia-Long [Science China Chemistry, 2018, vol. 61, # 2, p. 180 - 183]

71
[ 1200-07-3 ]
[ 156-41-2 ]
3-(4-bromophenyl)-N-[2-(4-chlorophenyl)ethyl]propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 48h; Inert atmosphere;	3.2.1. General Synthetic Procedure for Compounds 1-5 and 8 General procedure: The addition of 0.2 mmol of cinnamic acid together with equimolar amounts of DCC and theiramines in dichloromethane is done at 0 °C and stirred for 48 h under argon atmosphere. The reactionwas monitored by thin layer chromatography and purified through a silica gel chromatographiccolumn, eluting hexane and ethyl acetate (1:1) [9,24].

Reference： [1]Silveira, Graziela Rangel; Campelo, Karoline Azerêdo; Lima, Gleice Rangel Silveira; Carvalho, Lais Pessanha; Samarão, Solange Silva; Vieira-Da-Motta, Olney; Mathias, Leda; Matos, Carlos Roberto Ribeiro; Vieira, Ivo José Curcino; de Melo, Edesio José Tenório; Maria, Edmilson José [Molecules, 2018, vol. 23, # 4]

72
[ 1200-07-3 ]
[ 15687-27-1 ]
[ 683-18-1 ]
dibutyl((2-(4-isobutylphenyl)propanoyl)oxy)stannyl 3-(4-bromophenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In toluene at 80 - 110℃; for 18h;	Dibutyl(3-phenylpropanoyl) oxystannyl cinnamate (1). General procedure: In a dryflask, the hydrocinnamic acid (246 mg, 1.638 mmol) and the transcinnamicacid (242 mg, 1.633 mmol) were dissolved in 100ml ofdry toluene, next 0.874ml of triethylamine (660 mg, 6.581 mmol)was added, the mixture was stirred until its complete dissolution.On the reaction mixture at 80 °C is added dropwise the dibutyltindichloride (500 mg, 1.645 mmol) previously dissolved in 50ml oftoluene. Then, the mixture was heated to 110 °C for 6 h, after that,the heating was removed and kept for 12 h under continue stirring.The precipitated triethylamine hydrochloride was eliminated byfiltration and the toluene was evaporated under reduced pressure.The final product was washed three times with CH2Cl2 and H2O toremove any remaining triethylamine. The organic phase wastreated with MgSO4 to remove any residual water. Finally, theproduct was recovered by evaporation after removal of the hydratedMgSO4 by filtration. Compound 1 was obtained as a yellowliquid. Yield: 0.863 g (99%).

Reference： [1]Romero-Chávez, Maria M.; Pineda-Urbina, Kayim; Pérez, David J.; Obledo-Benicio, Fernando; Flores-Parra, Angelina; Gómez-Sandoval, Zeferino; Ramos-Organillo, Ángel [Journal of Organometallic Chemistry, 2018, vol. 862, p. 58 - 70]

73
[ 603-76-9 ]
[ 1200-07-3 ]
[ 22315-11-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sulfur; N,N-dimethyl-formamide at 150℃; for 16h; regioselective reaction;	Typical experimental procedure for the synthesis of 8-Methyl-2-phenyl-8H-thieno[2,3-b]indole 3aa: General procedure: 1-Methylindole 1a (26.2mg, 0.2 mmol), cinnamic acid 2a (59.3mg, 0.4mmol), sulfur powder (38.4mg, 1.2mmol) and DMF (0.3mL) were added to an oven-dried reaction vessel (20mL). The reaction vessel was sealed. The reaction vessel was stirred at 150 °C for 16h under air atmosphere. After the reaction was completed (TLC), the mixture was cooled to room temperature and then worked-up with ethyl acetate and water. The combined organic phase was dried over anhydrous Na2SO4, filtered, dried under reduced pressure and the crude product was purified by flash chromatography on silica gel by gradient elution (petroleum ether) to obtain the corresponding product 3aa.

Reference： [1]Zhang, Hao-Lin; Wen, Fei; Sheng, Wen-Bing; Yin, Peng; Zhang, Chun-Tao; Peng, Cai-Yun; Peng, Dong-Ming; Liao, Duan-Fang; Fu, Rong-Geng [Tetrahedron Letters, 2019, vol. 60, # 1, p. 80 - 83]

74
[ 1200-07-3 ]
C₁₅H₂₆N₂O [ No CAS ]
(Z)-(6S,7aR,13S,14aR)-tetradecahydro-6,13-methanodipyrido[1,2-a:1’2’-e][1,5]diazocin-2-yl-3-(4-bromophenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.22%	With triethylamine; dicyclohexyl-carbodiimide In acetonitrile at 80℃; for 8h;	15 Preparation of (Z)-(6S,7aR,13S,14aR)-tetradecahydro-6,13-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-2-yl 3-(4 -bromophenyl)acrylate (Compound O) The 25.02mg (0.10mmol) 13- hydroxy sparteine and 29.38mg (0.13mmol) 4- bromo-cinnamic acid was placed in a reaction vesselreactor, after addition of 50mL of acetonitrile sufficiently dissolved, was added 2.02 mg (0.02mmol) of triethylamine , 2.06mg (0.01mmol) DCC,reaction at 80 8 hours and rotary evaporated to dryness under reduced pressure, ethyl acetate was added dissolved organic matter, the organic layer with water, respectively, hydrogenwas washed with brine and sodium sulfate, reduced pressure The solvent was recovered by rotary distillation, and the concentrate was cooled and crystallized, and filtered to give30.34 mg of thecompound of the present invention, yield: 66.22%.

Reference： [1]Current Patent Assignee: SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108840871, 2018, A Location in patent: Paragraph 0045

75
[ 1200-07-3 ]
(1S,4S,5R)-3,3-dibenzyl-6,8-dioxabicyclo[3.2.1]-octan-4-ol [ No CAS ]
(1S,4S,5R)-3,3-dibenzyl-6,8-dioxabicyclo[3.2.1]octan-4-yl (E)-3-(4-bromophenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 22℃; for 12h; Inert atmosphere;	General procedure using DCC (GP2). General procedure: To a solution of alcohol 8 (1.0 equiv) in CH2Cl2 (2 mL/mmol 8) was added the appropriate acid (1.0 equiv) and DMAP (0.1 equiv). The solution was cooled to 0 °C and DCC (1.1 equiv) was added. The reaction was stirred at 0 °C for 5 min and then at 22 °C for 12 h. The precipitate was removed by filtration and the filtrate washed with H2O (20 mL/mmol 8) and CH2Cl2 (3 x 25 mL/mmol 8). The organic layers were combined, dried (MgSO4) and concentrated under reduced pressure. The residue was then purified by column chromatography on silica (EtOAc: hexanes 1:4) and then further purified as specified.

Reference： [1]Klepp, Julian; Podversnik, Harald; Puschnig, Johannes; Wallace, Andrew; Greatrex, Ben W. [Tetrahedron, 2019, vol. 75, # 29, p. 3894 - 3903]

76
[ 1200-07-3 ]
[ 873-55-2 ]
[ 41024-55-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dipotassium peroxodisulfate; oxygen In N,N-dimethyl-formamide at 100℃; for 12h;	General procedure for the synthesis of compounds 3: General procedure: A mixture of cinnamic acid 1 (1.0 mmol), K2S2O8 (1.5 mmol) and sodium sulfinate 2 (1.5 mmol) in DMF (5 mL) was stirred at 100 oC under ambient air for 12 h. Upon completion of the reaction (monitored by TLC), the mixture was extracted with EtOAc (3 x 15 mL). The combined organic phase was dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (EtOAc/n-hexane, 1:4) to afford an analytically pure sample of β-keto sulfones 3.

Reference： [1]Chawla; Kapoor, Ritu; Yadav, Lal Dhar S. [Tetrahedron Letters, 2019, vol. 60, # 34]

77
[ 1200-07-3 ]
[ 55394-81-5 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 16362 - 16373

78
[ 97-77-8 ]
[ 1200-07-3 ]
[ 42174-89-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	In 1,2-dichloro-ethane; at 90 - 100℃;Schlenk technique;	Take 4-bromocinnamic acid 0.5mmol and tetraethylthiuram disulfide 0.55mmolMake a mixture in 0.5 1ml of dichloroethane,Place the mixture in a 5ml Schlenk tube,Put it in an oil bath at 90 100 , after 36 48h reaction,Cool to room temperature to obtain the reaction solution;(2) The reaction solution obtained in step (1) is directly concentrated to obtain a concentrate,The concentrate was made with ethyl acetate / petroleum ether = 2/1 (v / v) as the developing agent,TLC separation was performed to obtain 82.0 mg of the target product.

Reference： [1]European Journal of Organic Chemistry,2020,vol. 2020,p. 198 - 208
[2]Patent: CN111018735,2020,A .Location in patent: Paragraph 0225-0231

79
[ 1200-07-3 ]
[ 14091-15-7 ]

Reference： [1]ChemCatChem,2020,vol. 12,p. 995 - 998

80
[ 1200-07-3 ]
[ 621-82-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With methanol; gold; hydrogen; caesium carbonate at 100℃; for 72h;

Reference： [1]Bao, Ming; Feng, Xiujuan; Yamamoto, Yoshinori; Zhang, Sheng; Zhao, Yuhui [ChemCatChem, 2020, vol. 12, # 19, p. 4951 - 4957]

81
[ 1200-07-3 ]
[ 333-20-0 ]
(E)-1-bromo-4-(2-thiocyanatovinyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With rose bengal; caesium carbonate In acetonitrile at 20℃; for 12h; Irradiation;	3 General Experimental Procedure In a flame-dried round bottom flask was equipped with a magnetic stirrer bar, cinnamic acid 1 (0.5mmol, 1 equiv), KSCN 2 (1.5mmol, 3 equiv), Rose Bengal (1mol%, 0.005equiv) and Cs2CO3 (1.5mmol, 3 equiv) were added in 5mL acetonitrile. The resulting mixture was stirred under irradiation with 23W CFL at room temperature. Upon completion of the reaction (monitored by TLC) after 12h, the reaction mixture was quenched with water and extracted with EtOAc (3 × 5mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo and the crude product was purified by silica gel chromatography (EtOAc/n-hexane,1:6) to afford an analytically pure sample of (E)-vinyl thiocyanates 3.

Reference： [1]Jaiswal, Deepali; Tiwari, Jyoti; Singh, Shailesh; Kartikey; Singh, Jaya; Singh, Jagdamba [Catalysis Letters, 2021, vol. 151, # 6, p. 1738 - 1744]

82
[ 1200-07-3 ]
C₁₈H₁₄O₄Se [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With selenium; potassium carbonate In water; dimethyl sulfoxide at 20℃; for 3h;

Reference： [1]Awasthi, Satish Kumar; Dixit, A. K.; Raghothama, S.; Yadav, Deepika [Dalton Transactions, 2020, vol. 49, # 35, p. 12266 - 12272]

83
[ 1200-07-3 ]
[ 480-40-0 ]
C₂₄H₁₅BrO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.5%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h; Inert atmosphere;	8 In a 50mL round-bottom flask, add chrysin (compound represented by structural formula (1)) (1mmol, 1eq), cinnamic acid (compound represented by structural formula (2h)) (1.5mmol, 1.5eq.), EDCI (1.5mmol). , 1.5eq) and DMAP (0.5mmol, 0.5eq), and then under the protection of N2, add dichloromethane (10.0mL), react at room temperature for about 6h (TLC detection), after the reaction is completed, filter with suction and remove the filter cake After washing with petroleum ether, ethyl acetate and acetone in sequence, it is dried to obtain compound 3h.Obtained compound 3h: yellow solid, yield 85.5%

Reference： [1]Current Patent Assignee: WUYI UNIVERSITY - CN111995605, 2020, A Location in patent: Paragraph 0004; 0019; 0044-0046

84
[ 851591-91-8 ]
[ 1200-07-3 ]
3β-(4-bromo)cinnamoyloxypregna-4,16-diene-6,20-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 3-(4-bromophenyl)acrylic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.25h; Stage #2: 3β-hydroxypregna-4,16-diene-6,20-dione In dichloromethane at 20℃;	General procedure for the synthesis of 3β-cinnamoyloxypregn-4,16-diene-6,20-diones 6a-g General procedure: The corresponding cinnamic acid derivative (3 mmol) wasstirred at room temperature with N,N0-dicyclohexylcarbodiimide(DCC, 2.3 mmol), and 4-dimethylaminopyridine (DMAP,2.7 mmol) in dichloromethane (20 mL) for 15 min. Then, steroid5 (1 mmol) was added, and the reaction mixture wasstirred between 60-90 min. Upon termination of the esterification,ethyl acetate (20 mL) was added, and the precipitatedicyclohexylurea was filtered. The solvent was removed atreduced pressure, and the solid obtained was stirred with a1:1 hexane: methanol solution using ethyl acetate as cosolventfor 30 min. The crude product was recrystallizedfrom methanol.

Reference： [1]Bratoeff, Eugene; Salazar, Juan Rodrigo; Sanabria-Chanaga, Elkin; Loza-Mejía, Marco A.; Mancha-Meléndez, Fernando Manuel; Meneses-Ruiz, Dulce María; Puertas-Santamaría, Erick Francisco [Journal of Biomolecular Structure and Dynamics, 2021]

85
[ 344-14-9 ]
[ 1200-07-3 ]
dimethyl (E)-2-(4-bromostyryl)-2-fluoromalonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With methanol; ferrocene; tetrabutylammonium tetrafluoroborate; sodium carbonate In tetrahydrofuran at 65℃; for 2.5h; Electrolysis; stereoselective reaction;

Reference： [1]Hou, Zhong-Wei; Jiang, Ting; Wang, Lei; Wu, Ting-Xia [Organic Letters, 2021, vol. 23, # 21, p. 8585 - 8589]

86
[ 1643-30-7 ]
[ 1200-07-3 ]

Yield	Reaction Conditions	Operation in experiment
61%	With tert.-butylhydroperoxide; 6-(quinolin-2-yl)pyridin-2(1H)-one; sodium acetate; palladium diacetate; lithium carbonate In 1,4-dioxane; tert-Amyl alcohol; water at 80℃; for 16h; Inert atmosphere;

Reference： [1]Wang, Zhen; Hu, Liang; Chekshin, Nikita; Zhuang, Zhe; Qian, Shaoqun; Qiao, Jennifer X.; Yu, Jin-Quan [Science, 2021, vol. 374, # 6572, p. 1281 - 1285]

87
[ 1200-07-3 ]
[ 155252-35-0 ]
C₃₁H₂₈BrNO₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-diethylpropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 25℃; for 5h;	General Method for Synthesizing 9a-y. General procedure: For use of carboxylic acids (condition c), 4β-aminopodophyllotoxin(7, 0.15 mmol, 1.0 eq), HATU (0.15 mmol, 1.0 eq), and diethylpropylamine (0.15 mmol, 1.0 eq) in CH2Cl2 (10 mL) wastreated with the appropriate carboxylic acid (0.225 mmol, 1.5 eq). The reaction mixture was stirred at room temperature for 5 hand diluted with H2O. The organic layer was washed with EtOAc (3 × 10 mL) and brine (10 mL), dried over Na2SO4, andevaporated. The crude product was purified by column chromatography (petroleum-ether-EtOAc, 1:1) to afford thetarget products. For acyl chlorides (condition d), a solution of 4β-aminopodophyllotoxin (7, 0.15 mmol, 1.0 eq) andEt3N (0.195 mmol, 1.3 eq) in CH2Cl2 (5 mL) was treated with the appropriate acyl chloride (0.195 mmol, 1.3 eq). Thereaction mixture was stirred at room temperature for 1 h and treated with H2O. The organic layer was washed with EtOAc(3 × 5 mL) and brine (5 mL), dried over Na2SO4, and evaporated. The product was purified by column chromatography(petroleum ether-EtOAc, 3:1-1:1) to afford the target products.

Reference： [1]Bozorov, K.; Cao, J.; Dai, X.; Guo, H.; Huang, G.; Lin, K.; Ma, L.; Zhang, X. [Chemistry of Natural Compounds, 2021, vol. 57, # 6, p. 1010 - 1018][Khim. Prir. Soedin., 2021, # 6, p. 866 - 873]

88
[ 1200-07-3 ]
[ 369-57-3 ]
(Z)-1-(4-bromophenyl)-2-phenylethylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium fluoride; tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate In dimethyl sulfoxide for 24h; Irradiation;	6 Example 6 Synthesis of 4-bromostilbene (Z configuration) Phenyldiazonium tetrafluoroborate (0.5mmol, 1equiv), 4-bromocinnamic acid (1.5mmol, 3equiv), KF (potassium fluoride) (1.5mmol, 3equiv), photocatalyst were added to a 10mL transparent glass bottle Photocatalyst [Ru(bpy)3]Cl2·6H2O (2.5% by mole), solvent DMSO (5mL, the solvent was degassed for 30min1h before use), and then placed under 40W blue light for 24h, After the reaction was complete, water (20 mL) was added to quench.The reaction solution was transferred to a separatory funnel, extracted three times with 15 mL of ethyl acetate each time, the organic phase was washed with saturated brine, then added with anhydrous magnesium sulfate and left to dry for 0.5 h. The filtrate was evaporated under reduced pressure, and then with petroleum ether/ethyl acetate (volume ratio of 20:1) as the eluent, the crude product was separated and purified by column chromatography, and the final product obtained was a yellow solid, and the yield was was 62%.

Reference： [1]Current Patent Assignee: MEDIUM MOUNTAIN UNIV - CN114163313, 2022, A Location in patent: Paragraph 0054-0056

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CAS No. :	1200-07-3	MDL No. :	MFCD00004394
Formula :	C₉H₇BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CPDDDTNAMBSPRN-ZZXKWVIFSA-N
M.W :	227.06	Pubchem ID :	737158
Synonyms :

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.81
TPSA :	37.3 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.9 cm/s

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	2.51
Log Po/w (WLOGP) :	2.44
Log Po/w (MLOGP) :	2.61
Log Po/w (SILICOS-IT) :	2.38
Consensus Log Po/w :	2.37

[ CAS No. 1200-07-3 ] {[proInfo.proName]}

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[ 1200-07-3 ] Synthesis Path-Upstream 1~12

[ 1200-07-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 1200-07-3 ]

Aryls

Alkenes

Bromides

Carboxylic Acids

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Log S (ESOL) :	-3.07
Solubility :	0.195 mg/ml ; 0.000857 mol/l
Class :	Soluble
Log S (Ali) :	-2.94
Solubility :	0.261 mg/ml ; 0.00115 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.72
Solubility :	0.433 mg/ml ; 0.00191 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.84

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 1200-07-3 ] {[proInfo.proName]}

Quality Control of [ 1200-07-3 ]

Related Doc. of [ 1200-07-3 ]

Product Details of [ 1200-07-3 ]

Calculated chemistry of [ 1200-07-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1200-07-3 ]

Application In Synthesis of [ 1200-07-3 ]

[ 1200-07-3 ] Synthesis Path-Upstream 1~12

[ 1200-07-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 1200-07-3 ]

Aryls

Alkenes

Bromides

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1200-07-3 ]