Name: 112-45-8|Undec-10-enal|97% (stabilized with α-tocopherol)
Brand: Ambeed
SKU: A246734
Price: 5.0 USD
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1
[ 112-43-6 ]
[ 112-45-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 10-Undecen-1-ol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78 - 23℃; for 1h; Inert atmosphere;
94%	With molecular sieve; tetrapropylammonium perruthenate (VII); N-Methylmorpholine N-oxide In dichloromethane at 20℃; for 1h;
93%	With pyridine; oxygen In toluene at 80℃; for 8h;

91%	With pyridine; 4 A molecular sieve; oxygen for 17h;
90%	With pyridinium chlorochromate In dichloromethane for 2h; Molecular sieve;	Undec-10-enal (3) In a 1 L flame-dried three-necked flask equipped with magnetic stirrer, were added dry dichloromethane (270 mL), pyridinium chlorochromate (85.44 g, 396.4 mmol), and finely crushed 3 Å molecular sieves (85 g). 10-undecen-1-ol (9spOH, available from commercialsource) was slowly added to the mixture (45 g, 264.2 mmol). After 2 hours, diethyl ether (270 mL)was added and the resulting heterogeneous mixture was poured in a 4 L beaker equipped with amagnetic stirrer containing diethyl ether (3 L). The remaining tar was triturated 3 times with diethyl ether (100 mL) and the resulting organic solutions were poured in the beaker. After the precipitated chromium byproduct and molecular sieves settled, the supernatant was purified by passing through a large silica plug. The solvents were removed in vacuo and the resulting dark oil was distilled over calcium hydride, affording a sweet-smelling clear liquid (40.1 g, 90%). The 1HNMR was consistent with the published spectrum.1
90%	With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate; isocyanuric acid In ethyl acetate at 0 - 10℃; for 4h;	General Procedure for theoxidation of alcohols employing nitroxyl radical / imide / NaOCl in thepresence of K₂CO₃. General procedure: To a mixture ofthe alcohol (3.839 mmol), K2CO3 (2.0 equiv, 7.678 mmol)and cyanuric acid (0.1 equiv, 0.384 mmol) in 20 mL of ethyl acetate were addedTEMPO or AZADO (3 mol%, 0.115 mmol) and 12% NaOCl (1.2 equiv, 4.607 mmol, Wako Pure Chemical Industries, Ltd.)at 0-10°C. The mixture was then stirred to complete. Thereaction mixture was extracted with ethyl acetate. The organic layer wasconcentrated under reduced pressure, and the residue was purified by silica gelcolumn chromatography to afford the corresponding product.
90%	With sodium chlorine monoxide; tetrabutylammonium bromide; Sodium hydrogenocarbonate; potassium bromide In dichloromethane; water monomer at 0℃; for 0.166667h; Schlenk technique;
89%	With pyridinium chlorochromate In dichloromethane at 20℃; for 5h;
88%	With pyridinium chlorochromate In dichloromethane at 23℃; for 16h; Inert atmosphere; Molecular sieve;
87%	With pyridine; air In toluene at 65℃; for 18h;
85%	With pyridinium chlorochromate In dichloromethane at -20℃; for 2h;
84%	With anhydrous Sodium acetate; pyridinium chlorochromate In dichloromethane
79%	Stage #1: 10-Undecen-1-ol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.25h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane for 0.5h; Inert atmosphere;
78%	With 2,2,6,6-tetramethyl-1-piperidinyloxy free radical; dimethylsulfane; oxygen In chlorobenzene at 90℃;
76%	With bis-trimethylsilanyl peroxide In dichloromethane at 25℃;
73%	With pyridinium chlorochromate In dichloromethane at 0℃; for 3h;
71%	With iodosylbenzene; ytterbium(III) nitrate In 1,2-dichloro-ethane at 80℃; for 4h;
70%	With N-Methylmorpholine N-oxide In dichloromethane for 3h; Ambient temperature;
70%	With NaBrO₃; NaHCO₃ buffer pH:10; anhydrous sodium carbonate In water monomer; 1,2-dichloro-ethane at 70℃; for 1.2h;
	With hydrogen; copper(II) oxide
92 % Chromat.	With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetra-n-butyl-ammonium chloride; Sodium hydrogenocarbonate; potassium carbonate In dichloromethane for 24h; Ambient temperature; pH 8.6;
22 % Chromat.	With pyridine; 4 A molecular sieve; oxygen In toluene at 100℃; for 1h;
100 % Chromat.	With N-chloro-succinimide; 4 A molecular sieve; potassium carbonate In dichloromethane at 20℃; for 0.5h;
77 % Chromat.	With N-tert-butylbenzenesulfinimidoyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; for 1h;
99 % Chromat.	With N-chloro-succinimide; N-tert-butylbenzenesulfenamide; potassium carbonate In dichloromethane at 20℃; for 0.5h;
	With poly[4-(diacetoxyiodo)styrene]; 2,2,6,6-tetramethyl-1-piperidinyloxy free radical In acetone at 20℃; for 4h;
	Multi-step reaction with 4 steps 1: 73 percent / triethylamine / CH₂Cl₂ / 0.25 h / 0 °C 2: 93 percent / NaI / acetone / 2 h 3: 72 percent / AgNO₂ / diethyl ether / a.) 0 deg C, 15 h, b.) room temperature, 8 h 4: 1.) NaH, tert-butyl alcohol, 2.)KMnO₄, H₃BO₃ / 1.) pentane, 20 min, 2.) benzene, water, 2 min
	Multi-step reaction with 2 steps 1: 1.) lead tetraacetate, Mn(OAc)2*4H₂O / 1.) benzene, reflux
	With pyridine-SO₃ complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h;
	With tetrapropylammonium perruthenate (VII); N-Methylmorpholine N-oxide In dichloromethane at 20℃; for 1h; Molecular sieve; Inert atmosphere;
	With Dess-Martin periodane In dichloromethane at 20℃; for 2h; Inert atmosphere;
50 mg	With hydrogenchloride; C₁₈H₃₈N₂O⁽¹⁺⁾*F₆P^(1-); 1-n-butyl-3-methylimidazolium bistrifluoromethylsulfonylamide; NaNO₂ In water monomer at 60℃; for 5h;
	With alcohol dehydrogenase from Escherichia coli; nicotinamide adenine dinucleotide In dimethyl sulfoxide at 25℃; Enzymatic reaction;
90 %Chromat.	With 3-(tert-butoxycarbonyl amino)-9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; NaNO₂ In acetic acid at 25℃; for 1.5h;	Typical procedure for the aerobic oxidation of p-methylbenzyl alcohol to p-methyl benzaldehyde (Table 2, entry 2): General procedure: A 25-mL tube equipped with a magnetic stirrer bar was added p-methylbenzyl alcohol (0.122 g, 1 mmol), sodium nitrite (5.5 mg, 8 mol%) and 3-(tert-butoxycarbonyl amino)-9-azabicyclo[3.3.1]nonane N-oxyl (3-BocNH-ABNO) (7.7 mg, 3 mol%). After the air in the tube was replaced with O2, 1 mL of acetic acid was added with syringe. Then the mixture was stirred under dioxygen atmosphere (balloon) at room temperature until the reaction was completed. After the reaction was finished, to the reaction mixture was added 8 mL of diethyl ether. Then the mixture was transferred into a separation funnel, and washed with saturated sodium bicarbonate solution (10 mL×3). The aqueous phase was extracted with 8 mL of ether. The combined organic phases was concentrated on a rotary evaporator and the residue was purified by column chromatography on silica gel using petroleumether/diethyl ether as eluent to afford p-methyl benzaldehyde as a colorless liquid; yield: 0.108 g (90%).
	With dmap; [2,2]bipyridinyl; copper (I) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 20℃; for 2h;

Reference： [1]Romano, Ciro; Mazet, Clément [Journal of the American Chemical Society, 2018, vol. 140, # 13, p. 4743 - 4750]
[2]Berube, Marie; Poirier, Donald [Organic Letters, 2004, vol. 6, # 18, p. 3127 - 3130]
[3]Uemura; Kakiuchi; Nishimura; Inoue [Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 1, p. 165 - 172]
[4]Nishimura, Takahiro; Kakiuchi, Nobuyuki; Onoue, Tomoaki; Ohe, Kouichi; Ucmura, Sakae [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 12, p. 1915 - 1918]
[5]Sauty, Nicolas F.; Li, Hong; Da Silva, Lucas Caire; Wagener, Kenneth B. [Synthetic Communications, 2014, vol. 44, # 16, p. 2409 - 2415]
[6]Fukuda, Naohiro; Izumi, Minoru; Ikemoto, Tomomi [Tetrahedron Letters, 2015, vol. 56, # 25, p. 3905 - 3908]
[7]Tian, Yangwu; Guo, Xiaqun; Li, Meichao; Li, Chunmei; Hu, Xinquan; Jin, Liqun; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu [Organic Letters, 2021, vol. 23, # 10, p. 3928 - 3932]
[8]Qin, Xiangdong; Tzvetkov, Tochko; Liu, Xin; Lee, Dong-Chan; Yu, Luping; Jacobs, Dennis C. [Journal of the American Chemical Society, 2004, vol. 126, # 41, p. 13232 - 13233]
[9]Ravu, Vengala Rao; Leung, Gulice Y. C.; Lim, Chek Shik; Ng, Sin Yee; Sum, Rong Ji; Chen, David Y.-K. [European Journal of Organic Chemistry, 2011, # 3, p. 463 - 468]
[10]Kakiuchi; Maeda; Nishimura; Uemura [Journal of Organic Chemistry, 2001, vol. 66, # 20, p. 6620 - 6625]
[11]Ishmuratov; Yakovleva; Kharisov; Muslukhov; Tolstikov [Russian Chemical Bulletin, 1997, vol. 46, # 5, p. 1035 - 1037]
[12]Cryle, Max J.; Matovic, Nick J.; de Voss, James J. [Organic Letters, 2003, vol. 5, # 18, p. 3341 - 3344]
[13]Tappin, Nicholas D. C.; Michalska, Weronika; Rohrbach, Simon; Renaud, Philippe [Angewandte Chemie - International Edition, 2019, vol. 58, # 40, p. 14240 - 14244][Angew. Chem., 2019, vol. 131, # 40, p. 14378 - 14382,5]
[14]Ragagnin, Gianna; Betzemeier, Bodo; Quici, Silvio; Knochel, Paul [Tetrahedron, 2002, vol. 58, # 20, p. 3985 - 3991]
[15]Kanemoto, Shigekazu; Oshima, Koichiro; Matsubara, Seijiro; Takai, Kazuhiko; Nozaki, Hitosi [Tetrahedron Letters, 1983, vol. 24, # 21, p. 2185 - 2188]
[16]Sharma; Sankaranarayanan; Chattopadhyay [Journal of Organic Chemistry, 1996, vol. 61, # 5, p. 1814 - 1816]
[17]Yokoo, Toshiaki; Matsumoto, Kozo; Oshima, Koichiro; Utimoto, Kiitiro [Chemistry Letters, 1993, # 3, p. 571 - 572]
[18]Griffith, William P.; Ley, Steven V.; Whitcombe, Gwynne P.; White, Andrew D. [Journal of the Chemical Society. Chemical communications, 1987, p. 1625 - 1627]
[19]Kanemoto, Shigekazu; Tomioka, Hiroki; Oshima, Koichiro; Nozaki, Hitosi [Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 105 - 108]
[20]Peterson,P.E.; Chevli,D.M. [Journal of Organic Chemistry, 1974, vol. 39, # 25, p. 3684 - 3691]
[21]Einhorn, Jacques; Einhorn, Cathy; Ratajczak, Fabien; Pierre, Jean-Louis [Journal of Organic Chemistry, 1996, vol. 61, # 21, p. 7452 - 7454]
[22]Coleman, Karl S.; Coppe, Maurice; Thomas, Christophe; Osborn, John A. [Tetrahedron Letters, 1999, vol. 40, # 19, p. 3723 - 3726]
[23]Mukaiyama, Teruaki; Matsuo, Jun-Ichi; Iida, Daisuke; Kitagawa, Hideo [Chemistry Letters, 2001, # 8, p. 846 - 847]
[24]Matsuo, Jun-Ichi; Iida, Daisuke; Tatani, Kazuya; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 2002, vol. 75, # 2, p. 223 - 234]
[25]Matsuo, Jun-Ichi; Iida, Daisuke; Yamanaka, Hiroyuki; Mukaiyama, Teruaki [Tetrahedron, 2003, vol. 59, # 35, p. 6739 - 6750]
[26]Tashino, Yousuke; Togo, Hideo [Synlett, 2004, # 11, p. 2010 - 2012]
[27]Kornblum, Nathan; Erickson, Allen S.; Kelly, William J.; Henggeler, Barbara [Journal of Organic Chemistry, 1982, vol. 47, # 23, p. 4534 - 4538]
[28]Mihailovic, M. Lj.; Konstantinovic, S.; Vukicevic, R. [Tetrahedron Letters, 1986, vol. 27, # 20, p. 2287 - 2290]
[29]Marshall, James A.; Sabatini, Jesse J.; Valeriote, Frederick [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2434 - 2437]
[30]Location in patent: scheme or table Berube, Marie; Poirier, Donald [Canadian Journal of Chemistry, 2009, vol. 87, # 8, p. 1180 - 1199]
[31]Halle, Mahesh B.; Fernandes, Rodney A. [RSC Advances, 2014, vol. 4, # 108, p. 63342 - 63348]
[32]Hirashita, Tsunehisa; Nakanishi, Makoto; Uchida, Tomoya; Yamamoto, Masakazu; Araki, Shuki; Arends, Isabel W. C. E.; Sheldon, Roger A. [ChemCatChem, 2016, vol. 8, # 16, p. 2704 - 2709]
[33]Bojarra, Samiro; Reichert, Dennis; Grote, Marius; Baraibar, Álvaro Gómez; Dennig, Alexander; Nidetzky, Bernd; Mügge, Carolin; Kourist, Robert [ChemCatChem, 2018, vol. 10, # 5, p. 1192 - 1201]
[34]Zhao, Yajing; Li, Yutong; Shen, Zhenlu; Hu, Xinquan; Hu, Baoxiang; Jin; Sun, Nan; Li, Meichao [Tetrahedron Letters, 2019, vol. 60, # 35]
[35]Bulska, Ewa; Enciso, Alan E.; Fantin, Marco; Grela, Karol; Lorandi, Francesca; Matyjaszewski, Krzysztof; Nogas, Wojciech; Piatkowski, Jakub; Ruszczynska, Anna; Szczepaniak, Grzegorz; Yerneni, Saigopalakrishna S. [Chemical Science, 2020, vol. 11, # 16, p. 4251 - 4262]
[36]Grosse, Michel; Günther, Kerstin; Jordan, Paul M.; Roman, Dávid; Werz, Oliver; Beemelmanns, Christine [ChemBioChem, 2022, vol. 23, # 9]

2
[ 67-56-1 ]
[ 112-45-8 ]
[ 65405-66-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With orthoformic acid triethyl ester for 12h; Heating / reflux;	1.1 Preparation of 11Silanyludecalal (1) First Stage: Synthesis of 11,11-dimethoxyundec-1-ene (7) 37.78 g of ethyl orthoformate (13.09 ml, 356 mmol, 2 eq.) and 1.691 g of para-toluenesulfonic acid (catalytic amount: 8.9 mmol, 0.051 eq.) are added to a solution of 30.05 g of 97% undecenal (37.10 ml, 173 mmol) dissolved in 500 ml of methanol. The reaction takes place over 12 hours and at reflux of the methanol. After addition of 500 ml of dichloromethane, the reaction mixture is washed successively with a 1% sodium carbonate solution (two times) and with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated to give 36.39 g of a brown liquid with a yield of 97%. The NMR analysis of the product obtained, in accordance with that of the product expected, was as follows: δH (200 MHz, CDCl3): 1.31 (12H, m, H4-9), 1.59 (2H, m, H10), 2.06 (2H, m, H)3.21 (6H, S, H12+13), 4.38 (1H, t, H11, 3JH-H 5.7 Hz), 4.98 (2H, m, H1), 5.81 (1H, m, H2), δc (200 MHz, CDCl3): 24.97, 29.30, 29.48, 29.76, 29.84, 29.87, 32.87, 34.18, 52.91 (C12+13), 104.94 (C11), 114.48 (C1), 139.54 (C2), m/z (NBA): 213 [M-H]+.
96%	With pyridinium p-toluenesulfonate for 17h; Ambient temperature;
92%	With ammonium chloride for 18h; Reflux; Inert atmosphere;

80%

With pyridinium p-toluenesulfonate at 20℃; for 20h; Inert atmosphere;

Reference： [1]Current Patent Assignee: UNIVERSITY OF MONTPELLIER; COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US2007/32672, 2007, A1 Location in patent: Page/Page column 5
[2]Trost, Barry M.; Kulawiec, Robert J. [Journal of the American Chemical Society, 1993, vol. 115, # 5, p. 2027 - 2036]
[3]Heberlig, Graham W.; Brown, Jesse T. C.; Simard, Ryan D.; Wirz, Monica; Zhang, Wei; Wang, Meng; Susser, Leah I.; Horsman, Mark E.; Boddy, Christopher N. [Organic and Biomolecular Chemistry, 2018, vol. 16, # 32, p. 5771 - 5779]
[4]Kemme, Susanne T.; Šmejkal, Tomáš; Breita, Bernhard [Advanced Synthesis and Catalysis, 2008, vol. 350, # 7-8, p. 989 - 994]

3
[ 38460-95-6 ]
[ 112-45-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tri-n-butyl-tin hydride; triphenylphosphine In tetrahydrofuran at -30℃; for 2h;
91%	With ammonium hydroxide; formic acid In diethyl ether; chloroform for 0.583333h; Ambient temperature;
86%	With tri-n-butyl-tin hydride In benzene for 1h; Ambient temperature;

40%	With iron(II) oxide; tris(2,4,6-trimethoxyphenyl)phosphine; phenylsilane In toluene at 60℃; for 2h; Inert atmosphere; Schlenk technique;	Catalytic reaction General procedure: A typical procedure for the iron oxide catalyzed reduction of 3-phenylpropionyl chloride (1a) with H3SiPh (Table1 , entry 1): iron oxide (3.6mg, 0.050mmol) and TMPP (6.7mg, 0.013mmol) were added to a 10mL Schlenk flask with a magnetic stir bar. The flask was evacuated and backfilled with argon three times. Then, H3SiPh (34μL, 0.28mmol) was added to the flask and the reaction mixture was stirred at 60°C for 20h under an argon atmosphere. Then, toluene (0.50mL) was added to the flask and the resultant solution was stirred at room temperature for 5min before 1a (37μL, 0.25mmol) was loaded. Further, the reaction mixture was stirred at 60°C for 20h under an argon atmosphere. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (5.0mL) and tetradecane (50μL, 0.19mmol) as an internal standard was added. The yield of 3-phenylpropanal (2a; 57%) was analyzed by gas chromatography. 2a was isolated by silica gel column chromatography (hexane: EtOAc=13: 1). Pale yellow oil (16.8mg) was obtained in 50% yield.
60 % Chromat.	With 4(P(C₆H₅)3)2Cu⁽¹⁺⁾2(BH₃)*2(CN)^(1-)={(P(C₆H₅)3)2CuBH₃(CN)}2 In acetone for 3h; Ambient temperature;
	Multi-step reaction with 3 steps 1: K₂CO₃ 2: acetone 3: 69 percent / diisobutylaluminum hydride / tetrahydrofuran / 0.5 h / -10 - 20 °C
	Multi-step reaction with 2 steps 1: Et₃N / CH₂Cl₂ 2: (i) LiAlH₄, tBuOH, (ii) aq. H₂SO₄, Na₂SO₄

Reference： [1]Inoue, Katsuyuki; Yasuda, Makoto; Shibata, Ikuya; Baba, Akio [Tetrahedron Letters, 2000, vol. 41, # 1, p. 113 - 116]
[2]Shamsuddin; Zobairi, Md. Omair; Musharraf, Mohd. Asif [Tetrahedron Letters, 1998, vol. 39, # 44, p. 8153 - 8154]
[3]Four, P.; Guibe, F. [Journal of Organic Chemistry, 1981, vol. 46, # 22, p. 4439 - 4445]
[4]Cong, Cong; Fujihara, Tetsuaki; Terao, Jun; Tsuji, Yasushi [Catalysis Communications, 2014, vol. 50, p. 25 - 28]
[5]Hutchins, Robert O.; Markowitz, Morris [Tetrahedron Letters, 1980, vol. 21, p. 813 - 816]
[6]De Las Heras, Maria A.; Vaquero, Juan J.; Garcia-Navio, Josel; Alvarez-Builla, Julio [Tetrahedron Letters, 1995, vol. 36, # 3, p. 455 - 458]
[7]Izawa,T.; Mukaiyama,T. [Bulletin of the Chemical Society of Japan, 1979, vol. 52, p. 555 - 558]

4
[ 112-45-8 ]
[ 75-16-1 ]
[ 21951-49-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	In diethyl ether at -40℃;
90%	In tetrahydrofuran at 0℃;
83%	In tetrahydrofuran; diethyl ether at -40 - 25℃; for 15h; Inert atmosphere;

62%	In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h;
59%	In diethyl ether for 14h;
50%	In diethyl ether at 0 - 35℃; for 3h; Inert atmosphere;
	In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;

Reference： [1]Cryle, Max J.; Matovic, Nick J.; de Voss, James J. [Organic Letters, 2003, vol. 5, # 18, p. 3341 - 3344]
[2]Pungente, Michael D.; Weiler, Larry [Organic Letters, 2001, vol. 3, # 5, p. 643 - 646]
[3]Tappin, Nicholas D. C.; Michalska, Weronika; Rohrbach, Simon; Renaud, Philippe [Angewandte Chemie - International Edition, 2019, vol. 58, # 40, p. 14240 - 14244][Angew. Chem., 2019, vol. 131, # 40, p. 14378 - 14382,5]
[4]Qin, Xiangdong; Tzvetkov, Tochko; Liu, Xin; Lee, Dong-Chan; Yu, Luping; Jacobs, Dennis C. [Journal of the American Chemical Society, 2004, vol. 126, # 41, p. 13232 - 13233]
[5]Powell, David A.; Maki, Toshihide; Fu, Gregory C. [Journal of the American Chemical Society, 2005, vol. 127, # 2, p. 510 - 511]
[6]Dong, Wenke; Yang, Hongxuan; Yang, Wen; Zhao, Wanxiang [Organic Letters, 2020]
[7]Sinha; Sinha-Bagchi; Keinan [Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7789 - 7796]
[8]Mahattanatawee, Kanjana; Luanphaisarnnont, Torsak; Rouseff, Russell [Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 10, p. 2480 - 2484]

6
[ 112-45-8 ]
[ 26116-56-3 ]
[ 112452-21-8 ]

Yield	Reaction Conditions	Operation in experiment
27%	With hydrogenchloride; sodium phosphate buffer; sodium cyanoborohydride In acetonitrile for 1.5h; Ambient temperature;

Reference： [1]Kirst, Herbert A.; Wind, Julie A.; Leeds, James P.; Willard, Kevin E.; Debono, Manuel; et al. [Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 3086 - 3094]

7
[ 112-45-8 ]
[ 112-38-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tris[2-(4,6-difluorophenyl)pyridinato-C²,N]-iridium(III); oxygen In acetonitrile at 20℃; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;	Synthesis of carboxylic acids General procedure: An oven-dried resealable test tube equipped with a magnetic stir bar was charged withaldehyde (1.0 mmol), Ir(dFppy)3 (0.005-0.01 mmol), and MeCN (4.0 mL, 0.25 M). Oxygen wasthen bubbled through the reaction mixture and sealed with a silicone septa screw-cap. A balloonfilled with oxygen was attached to the tube, and the test tube was placed under blue LEDs atroom temperature. The reaction was allowed to proceed for 3-12 h, and reaction progress waschecked by TLC. The solvent was removed under vacuum, and the corresponding carboxylic acidwas purified by flash silica gel chromatography.
87%	With tetrabutyl-ammonium chloride; dihydrogen peroxide; potassium carbonate In tetrahydrofuran Ambient temperature; without CeCl₃*7H₂O;
87%	With tetrabutyl-ammonium chloride; dihydrogen peroxide; potassium carbonate In tetrahydrofuran Ambient temperature;

84%	With dipyridinium dichromate
73%	With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In <i>tert</i>-butyl alcohol at 0℃; for 2h; Inert atmosphere;
70%	With 1-hydroxycyclohexyl phenyl ketone; sodium hydroxide In 1,2-dimethoxyethane at 80℃; Sealed tube;
	With sodium hydroxide 1.) 19 h reflux; 2.) 24 h reflux; Yield given. Multistep reaction;
85 % Spectr.	With dihydrogen peroxide In water at 90℃; for 2h;
	With poly[4-(diacetoxyiodo)styrene]; 2,2,6,6-tetramethyl-piperidine-N-oxyl In acetone at 20℃; for 24h;
	Multi-step reaction with 2 steps 1: 92 percent / trityl perchlorate / CH₂Cl₂ / 3 h / -45 °C 2: 76 percent / piperidine / H₂O / 3 h / 90 °C
90 %Chromat.	With dihydrogen peroxide In water at 90℃; for 2h;	10 Example 10 Example 10 Nafion NR50 (500 mg), 30% aqueous hydrogen peroxide solution (1.3 mL, 11 mmol), and 10-undecenaldehyde (2.1 mL, 10 mmol) were mixed and stirred at 90° C. for 2 hours. After the reaction solution was cooled to room temperature, the yield of 10-undecenoic acid by measurement of GLC was 90%.
	With alcohol dehydrogenase from Escherichia coli; nicotinamide adenine dinucleotide In dimethyl sulfoxide at 25℃; Enzymatic reaction;

Reference： [1]Iqbal, Naeem; Choi, Sungkyu; You, Youngmin; Cho, Eun Jin [Tetrahedron Letters, 2013, vol. 54, # 46, p. 6222 - 6225]
[2]Trost, Barry M.; Masuyama, Yoshiro [Tetrahedron Letters, 1984, vol. 25, # 2, p. 173 - 176]
[3]Trost, Barry M.; Masuyama, Yoshiro [Tetrahedron Letters, 1984, vol. 25, # 2, p. 173 - 176]
[4]Clarembeau, M.; Cravador, A.; Dumont, W.; Hevesi, L; Krief, A.; et al. [Tetrahedron, 1985, vol. 41, # 21, p. 4793 - 4812]
[5]Ravu, Vengala Rao; Leung, Gulice Y. C.; Lim, Chek Shik; Ng, Sin Yee; Sum, Rong Ji; Chen, David Y.-K. [European Journal of Organic Chemistry, 2011, # 3, p. 463 - 468]
[6]Tan, Wen-Yun; Lu, Yi; Zhao, Jing-Feng; Chen, Wen; Zhang, Hongbin [Organic Letters, 2021, vol. 23, # 17, p. 6648 - 6653]
[7]Ganem, Bruce; Heggs, Richard P.; Biloski, Alan J.; Schwartz, Daniel R. [Tetrahedron Letters, 1980, vol. 21, p. 685 - 688]
[8]Sato, Kazuhiko; Hyodo, Mamoru; Takagi, Junko; Aoki, Masao; Noyori, Ryoji [Tetrahedron Letters, 2000, vol. 41, # 9, p. 1439 - 1442]
[9]Tashino, Yousuke; Togo, Hideo [Synlett, 2004, # 11, p. 2010 - 2012]
[10]Mukaiyama, Teruaki; Miyoshi, Norikazu; Kato, Jun-ichi; Ohshima, Masahiro [Chemistry Letters, 1986, p. 1385 - 1388]
[11]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - US2006/167311, 2006, A1 Location in patent: Page/Page column 4
[12]Bojarra, Samiro; Reichert, Dennis; Grote, Marius; Baraibar, Álvaro Gómez; Dennig, Alexander; Nidetzky, Bernd; Mügge, Carolin; Kourist, Robert [ChemCatChem, 2018, vol. 10, # 5, p. 1192 - 1201]

8
[ 112-45-8 ]
[ 107-21-1 ]
[ 6316-55-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With toluene-4-sulfonic acid In benzene at 80℃; for 2h;
97%	In tetrachloromethane for 24h; Heating;
95%	With toluene-4-sulfonic acid In water; benzene

90%	With toluene-4-sulfonic acid In benzene Heating;
90%	With toluene-4-sulfonic acid In water; benzene for 8h; Inert atmosphere; Reflux;

Reference： [1]Magdziak, Derek; Lalic, Gojko; Lee, Hong Myung; Fortner, Kevin C.; Aloise, Allen D.; Shair, Matthew D. [Journal of the American Chemical Society, 2005, vol. 127, # 20, p. 7284 - 7285]
[2]Kamitori, Yasuhiro; Hojo, Masaru; Masuda, Ryoichi; Yoshida, Tatsushi [Tetrahedron Letters, 1985, vol. 26, # 39, p. 4767 - 4770]
[3]Clarembeau, M.; Cravador, A.; Dumont, W.; Hevesi, L; Krief, A.; et al. [Tetrahedron, 1985, vol. 41, # 21, p. 4793 - 4812]
[4]Sinha; Sinha-Bagchi; Keinan [Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7789 - 7796]
[5]Location in patent: experimental part Lipshutz, Bruce H.; Ghorai, Subir; Leong, Wendy Wen Yi; Taft, Benjamin R.; Krogstad, Daniel V. [Journal of Organic Chemistry, 2011, vol. 76, # 12, p. 5061 - 5073]

9
[ 112-45-8 ]
[ 107-18-6 ]
[ 114837-51-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: allyl alcohol With chloro-trimethyl-silane; sodium iodide In acetonitrile at 20℃; for 12h; Stage #2: With bismuth In acetonitrile at 20℃; for 1h; Stage #3: 10-Undecenal In acetonitrile for 22h;
65%	In various solvent(s) at 25℃; for 39h;
65%	With bis(benzonitrile)palladium(II) dichloride; tin(ll) chloride In various solvent(s) at 25℃; for 39h;

54%	With tin(II) iodide; tetra-(n-butyl)ammonium iodide; sodium iodide In water at 60℃; for 46h;
53%	With tin(ll) chloride In tetrahydrofuran; water at 20℃; for 47h;

Reference： [1]Wada; Miyoshi; Nishio; Murakami; Fukuma [Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 3, p. 689 - 692]
[2]Masuyama, Yoshiro; Takahara, Jun P.; Kurusu, Yasuhiko [Journal of the American Chemical Society, 1988, vol. 110, # 13, p. 4473 - 4474]
[3]Takahara, Jun P.; Masuyama, Yoshiro; Kurusu, Yasuhiko [Journal of the American Chemical Society, 1992, vol. 114, # 7, p. 2577 - 2586]
[4]Masuyama, Yoshiro; Ito, Takanori; Tachi, Kentaro; Ito, Akihiro; Kurusu, Yasuhiko [Chemical Communications, 1999, # 13, p. 1261 - 1262]
[5]Masuyama, Yoshiro; Chiyo, Toshiya; Kurusu, Yasuhiko [Synlett, 2005, # 14, p. 2251 - 2253]

10
[ 112-45-8 ]
[ 108-46-3 ]
[ 155401-88-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogenchloride In ethanol at 60℃; for 25h;
49%	With hydrogenchloride In ethanol; water at 0℃; for 13h; Reflux;	Synthesis of calixresorcinarenes General procedure: The synthesis was carried out based on the following recipe: 0.23 mol of resorcinol and 0.23 mol of aldehyde were dissolved into 240 mL absolute ethanol. The solution was cooled down to 0 C in an ice bath, and then 37 mL of concentrated hydrochloric acid was injected, and it was stirred for 1 h, then heated and refluxed for another 12 h. When the mixture was cooled down to room temperature, most of the product precipitated. Excess of water was added to completely precipitate the formed calix resorcinarene,which was filtered on a glass frit G3 type. The solid material was rinsed by distilled water and dried in vacuum over NaOH or P2O5. The recrystallization from methanol and then from an acetone/hexane 1:1 mixture gave a yield of 49%, 50% and 48.8%, respectively, for the compounds CAL 11U, CAL 9U and CAL 10.
42%	With hydrogenchloride In ethanol

36%	With hydrogenchloride In ethanol; water Inert atmosphere; Cooling with ice; Reflux;
20%	With hydrogenchloride at 60℃; for 16h;
	With hydrogenchloride In ethanol
	With hydrogenchloride In ethanol

Reference： [1]Yamakoshi; Schlittler; Gimzewski; Diederich [Journal of Materials Chemistry, 2001, vol. 11, # 12, p. 2895 - 2897]
[2]Eddaif, Larbi; Trif, László; Telegdi, Judit; Egyed, Orsolya; Shaban, Abdul [Journal of Thermal Analysis and Calorimetry, 2019, vol. 137, # 2, p. 529 - 541]
[3]Ruderisch, Alexander; Pfeiffer, Jens; Schurig, Volker [Tetrahedron Asymmetry, 2001, vol. 12, # 14, p. 2025 - 2030]
[4]Location in patent: experimental part Helttunen, Kaisa; Prus, Piotr; Luostarinen, Minna; Nissinen, Maija [New Journal of Chemistry, 2009, vol. 33, # 5, p. 1148 - 1154]
[5]Thoden Van Velzen, Eggo U.; Engbersen, Johan F. J.; Reinhoudt, David N. [Journal of the American Chemical Society, 1994, vol. 116, # 8, p. 3597 - 3598]
[6]Adams, Harry; Davis, Frank; Stirling, Charles J. M. [Journal of the Chemical Society. Chemical communications, 1994, # 21, p. 2527 - 2530]
[7]Schaefer, Christian; Eckel, Rainer; Ros, Robert; Mattay, Jochen; Anselmetti, Dario [Journal of the American Chemical Society, 2007, vol. 129, # 6, p. 1488 - 1489]

11
[ 112-45-8 ]
[ 112-43-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 10-Undecenal With [CpFe(IMes)(CO)2]I; phenylsilane In tetrahydrofuran at 70℃; for 1h; Inert atmosphere; Irradiation; Stage #2: With methanol; sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere;
96%	Stage #1: 10-Undecenal With (dppe)2Fe(H)2*(C₇H₈)2; Na-tetrakis(ethoxy)borate In toluene at 100℃; for 1h; visible light irradiation; Inert atmosphere; Stage #2: With water; sodium hydroxide In methanol; toluene at 20℃; for 16h;
94%	With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h;

93%	Stage #1: 10-Undecenal With polymethylhydrosiloxane; P(MeNCH₂CH₂)3N In tetrahydrofuran at 20℃; for 1h; Stage #2: In tetrahydrofuran at 20℃; for 1h;
85%	With (ethylenediamine)[1,2-bis(diphenylphosphino)ethane]ruthenium(II)[bis(adamantane-1-carboxylate)]; hydrogen; benzoic acid In n-heptane at 70℃; Autoclave; Inert atmosphere;	6 Undec-10-en-1-ol synthesis Undec-10-enal (84 g, 0.5 mol.), heptane (84 g, 100 wt. %, technical grade), and (ethylenediamine)[1,2-bis(diphenylphosphino)ethane]ruthenium[bis((adamantane-1-carboxylate)] (45.9 mg, 0.05 mmol, 0.01 mol.%) were loaded altogether in a 300 ml autoclave equipped with a mechanical stirring device. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to 10 bars hydrogen. It was then heated to 70° C. and hydrogen pressure was maintained to 10 bars during all the reaction to afford desired product with 90% selectivity. After complete reaction conversion (checked by both hydrogen consumption and GC), autoclave was cooled down to 25° C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and solvent was removed under vacuum. After initial flash distillation and further fractional distillation, undec-10-en-1-ol was obtained in 85% yield.
82%	With indium isopropoxide; isopropyl alcohol at 25℃; for 3h; Inert atmosphere;
80%	With trichlorosilane; N,N-dimethyl-formamide In dichloromethane at 0℃; for 6h;
77%	Stage #1: 10-Undecenal With nickel(II) acetate tetrahydrate; tricyclohexylphosphine In tetrahydrofuran at 70℃; for 16h; Stage #2: With sodium hydroxide In methanol
71%	Stage #1: 10-Undecenal With Cp(CO)2Mn(IMes); diphenylsilane In toluene at 25℃; for 8h; Schlenk technique; Inert atmosphere; UV-irradiation; Stage #2: With sodium hydroxide In methanol; toluene at 20℃; for 2h; Schlenk technique; Inert atmosphere;
68%	With [Ni(1,3-dimesitylimidazol-2-ylidene)Clcyclopentadienyl]; sodium triethylborohydride; diphenylsilane In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Schlenk technique; chemoselective reaction;
58%	With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; tris[3,5-bis(trifluoromethyl)phenyl]-borane In 1,4-dioxane at 100℃; for 12h; Glovebox;	General procedure for the hydrogenation reaction General procedure: In a glovebox, aldehydes (0.25 mmol) and the Hantzsch ester 1 (95 mg, 0.38 mmol) were added to asolution of tris[3,5-bis(trifluoromethy)phenyl]borane (9) (8.1 mg, 12.5 μmol) in 1 mL of anhydrous1,4-dioxane. The reaction mixture was stirred at 25 or 100 C for 12 h. An internal standard (biphenylor mesitylene) was added to the reaction mixture and filtrated through a cotton plug. The resultingsolution was analyzed with gas chromatography.
	Multi-step reaction with 2 steps 1: [CpFe(IMes)(CO₂)]I / 3 h / 30 °C / Inert atmosphere; Neat (no solvent); visible light irradiation 2: sodium hydroxide / methanol; water / 1 h / 20 °C
	With (ethylenediamine)[1,2-bis(diphenylphosphino)ethane]ruthenium(II)[bis(adamantane-1-carboxylate)]; hydrogen In n-heptane at 80℃; for 16h; Autoclave; chemoselective reaction;
95 %Chromat.	With C₁₈H₃₂BrFeNO₃P₂; sodium formate In methanol; dodecane at 40℃; for 6h; Inert atmosphere; chemoselective reaction;
	With hydrogen In isopropyl alcohol at 149.84℃; for 0.5h; Autoclave; chemoselective reaction;
	With dichloro(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II); sodium formate; trimethyldodecylammonium chloride In water at 85℃; Schlenk technique;
	With sodium tetrahydroborate In methanol at 0℃; for 1h;

Reference： [1]Jiang, Fan; Bezier, David; Sortais, Jean-Baptiste; Darcel, Christophe [Advanced Synthesis and Catalysis, 2011, vol. 353, # 2-3, p. 239 - 244]
[2]Castro, Luis C. Misal; Bezier, David; Sortais, Jean-Baptiste; Darcel, Christophe [Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1279 - 1284]
[3]Ravikumar; Chandrasekaran, Srinivasan [Journal of Organic Chemistry, 1996, vol. 61, # 3, p. 826 - 830]
[4]Wang, Zhigang; Wroblewski, Andrzej E.; Verkade, John G. [Journal of Organic Chemistry, 1999, vol. 64, # 21, p. 8021 - 8023]
[5]Current Patent Assignee: Firmenich International SA - US2014/243526, 2014, A1 Location in patent: Paragraph 0207
[6]Lee, Jaeyoung; Ryu, Taekyu; Park, Sangjune; Lee, Phil Ho [Journal of Organic Chemistry, 2012, vol. 77, # 10, p. 4821 - 4825]
[7]Kobayashi, Shu; Yasuda, Masaru; Hachiya, Iwao [Chemistry Letters, 1996, # 5, p. 407 - 408]
[8]Zheng, Jianxia; Darcel, Christophe; Sortais, Jean-Baptiste [Catalysis science and technology, 2013, vol. 3, # 1, p. 81 - 84]
[9]Zheng, Jianxia; Elangovan, Saravanakumar; Valyaev, Dmitry A.; Brousses, Remy; Cesar, Vincent; Sortais, Jean-Baptiste; Darcel, Christophe; Lugan, Noel; Lavigne, Guy [Advanced Synthesis and Catalysis, 2014, vol. 356, # 5, p. 1093 - 1097]
[10]Bheeter, Linus P.; Henrion, Mickael; Brelot, Lydia; Darcel, Christophe; Chetcuti, Michael J.; Sortais, Jean-Baptiste; Ritleng, Vincent [Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2619 - 2624]
[11]Hamasaka, Go; Tsuji, Hiroaki; Uozumi, Yasuhiro [Synlett, 2015, vol. 26, # 14, p. 2037 - 2041]
[12]Bezier, David; Jiang, Fan; Roisnel, Thierry; Sortais, Jean-Baptiste; Darcel, Christophe [European Journal of Inorganic Chemistry, 2012, # 9, p. 1333 - 1337]
[13]Dupau, Philippe; Bonomo, Lucia; Kermorvan, Laurent [Angewandte Chemie - International Edition, 2013, vol. 52, # 43, p. 11347 - 11350][Angew. Chem., 2013, p. 11557 - 11560]
[14]Mazza, Simona; Scopelliti, Rosario; Hu, Xile [Organometallics, 2015, vol. 34, # 8, p. 1538 - 1545]
[15]Putro, Wahyu S.; Kojima, Takashi; Hara, Takayoshi; Ichikuni, Nobuyuki; Shimazu, Shogo [Catalysis science and technology, 2017, vol. 7, # 16, p. 3637 - 3646]
[16]Öztürk, Bengi Özgün; Öztürk, Sinem [Molecular catalysis, 2020, vol. 480]
[17]Calamante, Massimo; Dei, Filippo; Maramai, Samuele; Migliorini, Francesca; Petricci, Elena [ChemCatChem, 2021, vol. 13, # 12, p. 2794 - 2806]

12
[ 112-45-8 ]
[ 60754-70-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 4-methoxypyridine N-oxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 30h;
58%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 80℃; for 12h;
58%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 80℃; for 12h;

Reference： [1]Nicolaou; Montagnon, Tamsyn; Baran, Phil S. [Angewandte Chemie - International Edition, 2002, vol. 41, # 6, p. 993 - 996]
[2]Nicolaou; Montagnon; Baran; Zhong [Journal of the American Chemical Society, 2002, vol. 124, # 10, p. 2245 - 2258]
[3]Nicolaou; Zhong; Baran [Journal of the American Chemical Society, 2000, vol. 122, # 31, p. 7596 - 7597]

13
[ 112-38-9 ]
[ 112-45-8 ]
(E)-9-undecenal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogen; 2,2-dimethylpropanoic anhydride In N,N-dimethyl-formamide at 80℃; for 5h;

Reference： [1]Nagayama; Shimizu; Yamamoto [Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 10, p. 1803 - 1815]

14
[ 112-45-8 ]
[ 553664-70-3 ]
(E)-(R)-Hexadeca-3,15-dien-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With toluene-4-sulfonic acid In dichloromethane at 20℃; for 20h;

Reference： [1]Nokami, Junzo; Nomiyama, Kenta; Matsuda, Seiji; Imai, Nobuyuki; Kataoka, Kazuhide [Angewandte Chemie - International Edition, 2003, vol. 42, # 11, p. 1273 - 1276]

15
[ 75-47-8 ]
[ 112-45-8 ]
[ 126347-88-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With chromium chloride; chloro-trimethyl-silane; zinc In 1,4-dioxane at 25℃; for 24h;

Reference： [1]Gallagher, William P.; Maleczka Jr., Robert E. [Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6775 - 6779]

16
[ 75-47-8 ]
[ 112-45-8 ]
(E)-1-Iodo-dodeca-1,11-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With chromium dichloride In tetrahydrofuran at 0℃; for 2h;
	With chromium dichloride In tetrahydrofuran at 0℃; for 2h;

Reference： [1]Takai, Kazuhiko; Toshikawa, Shota; Inoue, Atsushi; Kokumai, Ryo [Journal of the American Chemical Society, 2003, vol. 125, # 43, p. 12990 - 12991]
[2]Takai, Kazuhiko; Toshikawa, Shota; Inoue, Atsushi; Kokumai, Ryo; Hirano, Masato [Journal of Organometallic Chemistry, 2007, vol. 692, # 1-3, p. 520 - 529]

17
[ 864953-57-1 ]
[ 112-45-8 ]
[ 736140-88-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile at 20℃; for 15h;

Reference： [1]Yamagiwa, Noriyuki; Qin, Hongbo; Matsunaga, Shigeki; Shibasaki, Masakatsu [Journal of the American Chemical Society, 2005, vol. 127, # 38, p. 13419 - 13427]

18
[ 112-45-8 ]
[ 36219-78-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With water; oxygen; copper(l) chloride In tetrahydrofuran at 20℃; for 36h;
80%	With palladium diacetate; Dess-Martin periodane In water; acetonitrile at 50℃; Inert atmosphere;
75%	With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium perchlorate In water; acetonitrile at 20℃; Electrochemical reaction;

Reference： [1]Donck, Simon; Gravel, Edmond; Shah, Nimesh; Jawale, Dhanaji V.; Doris, Eric; Namboothiri, Irishi N. N. [ChemCatChem, 2015, vol. 7, # 15, p. 2318 - 2322]
[2]Chaudhari, Dipali A.; Fernandes, Rodney A. [Journal of Organic Chemistry, 2016, vol. 81, # 5, p. 2113 - 2121]
[3]Mitsudo, Koichi; Kaide, Takashi; Nakamoto, Eriko; Yoshida, Kenta; Tanaka, Hideo [Journal of the American Chemical Society, 2007, vol. 129, # 8, p. 2246 - 2247]

19
[ 4899-94-9 ]
[ 112-45-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.75h;
	Multi-step reaction with 2 steps 1: Ti(O-i-Pr)4, Ph₂SiH₂ / 5 h / 20 °C 2: 1 M aq. HCl / tetrahydrofuran / 20 °C

Reference： [1]Spletstoser, Jared T.; White, Jonathan M.; Tunoori, Ashok Rao; Georg, Gunda I. [Journal of the American Chemical Society, 2007, vol. 129, # 11, p. 3408 - 3419]
[2]Bower, Shelley; Kreutzer, Kristina A.; Buchwald, Stephen L. [Angewandte Chemie, 1996, vol. 108, # 13/14, p. 1662 - 1664]

20
[ 112-45-8 ]
[ 75-05-8 ]
12-cyano-11-hydroxydodec-1-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N,N,N,N,N-hexamethylphosphoric triamide at 50℃; for 24h;
63%	With N,N,N,N,N,N-hexamethylphosphoric triamide; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene at 50℃; for 24h;

Reference： [1]Kumagai, Naoya; Matsunaga, Shigeki; Shibasaki, Masakatsu [Chemical Communications, 2005, # 28, p. 3600 - 3602]
[2]Kumagai, Naoya; Matsunaga, Shigeki; Shibasaki, Masakatsu [Tetrahedron, 2007, vol. 63, # 35, p. 8598 - 8608]

21
[ 112-45-8 ]
[ 33189-72-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) Mg / 1.) THF, 2.) THF, -15 deg C, 1 h, 20 deg C, 12 h 2: 93 percent / DMAP / pyridine / 48 h 3: 85 percent / CuI / tetrahydrofuran / 2 h / -10 °C 4: 1.) BBN, 2.) H₂O₂, NaOAc / 1.) THF, 10 deg C, 2 h, 2.) THF, H₂O, 25 deg C, 2 h 5: 92 percent / pyridine

Reference： [1]Ishmuratov; Yakovleva; Kharisov; Muslukhov; Tolstikov [Russian Chemical Bulletin, 1997, vol. 46, # 5, p. 1035 - 1037]

22
[ 112-45-8 ]
[ 34010-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: diethyl ether / 4 h / 0 - 2 °C 2: 79 percent / pyridine / 1.) -5 deg C, 6 h; 2.) 0 deg C, 12 h 3: 53 percent / sodium iodide, zinc dust / tetrahydrofuran / 1.) 65-70 deg C, 3 h; 2.) 20 deg C, 3 h 4: 1.) 2percent O₃ in O₂; 2.) sodium tetrahydroborate / 1.) cyclohexane, methanol; 2.) room temp., 15 h 5: 1.) isobutylmagnesium bromide; 2.) C₅H₅TiCl₂ / 1.) diethyl ether, 0 deg C, 15 min; 2.) room temp., 1-1,5 h 6: 90 percent / pyridine
	Multi-step reaction with 3 steps 1: (i) Na3)2>, THF, (ii) /BRN= 1746480/ 2: 9-BBN / tetrahydrofuran 3: Py / 3 h / Heating

Reference： [1]Odinokov, V. N.; Ishmuratov, G. Yu.; Ladenkova, I. M.; Tolstikov, G. A. [Chemistry of Natural Compounds, 1987, vol. 23, # 3, p. 365 - 368][Khimiya Prirodnykh Soedinenii, 1987, # 3, p. 440 - 444]
[2]Bestmann; Kantardjiew; Roesel; et al. [Chemische Berichte, 1978, vol. 111, # 1, p. 248 - 253]

23
[ 626-55-1 ]
[ 112-45-8 ]
2-(3-pyridinyl)-10-undecanal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 6h;

Reference： [1]Martin, Ruben; Buchwald, Stephen L. [Angewandte Chemie - International Edition, 2007, vol. 46, # 38, p. 7236 - 7239]

24
[ 112-45-8 ]
[ 515-84-4 ]
[ 1059581-55-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With Rieke-manganese In tetrahydrofuran for 5h; Inert atmosphere; Reflux; optical yield given as %de; stereoselective reaction;
87%	With manganese In tetrahydrofuran for 5h; Reflux; Inert atmosphere; stereoselective reaction;

Reference： [1]Location in patent: experimental part Concellon, Jose M.; Rodriguez-Solla, Humberto; Diaz, Pamela [Organic and Biomolecular Chemistry, 2008, vol. 6, # 16, p. 2934 - 2940]
[2]Location in patent: experimental part Concellon, Jose M.; Rodriguez-Solla, Humberto; Del Amo, Vicente; Diaz, Pamela [Synthesis, 2009, # 15, p. 2634 - 2645]

25
[ 112-45-8 ]
[ 124931-12-0 ]
[ 1222465-49-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: 10-Undecenal In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.75h;

Reference： [1]Donohoe, Timothy J.; Bower, John F. [Proceedings of the National Academy of Sciences of the United States of America, 2010, vol. 107, # 8, p. 3373 - 3376]

26
[ 112-45-8 ]
[ 60556-38-9 ]
[ 1373211-70-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 10-Undecenal; tert-butyltrifluorosilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 3h; Stage #2: With hydrogenchloride In tetrahydrofuran; water	3.2. Preparation of the fluorinated alcohols 2 Typical procedure: a mixture of 10-undecenal (1.68 g, 10 mmol) and CF3SiMe3 (1.71 g, 1.9 mL, 12 mmol) in 15 mL of THF, which was cooled to 0 °C, was treated with 1 M THF solution of TBAF (15 mol%, 15 mL, 1.5 mmol). The reaction mixture was brought to room temperature and stirred for 3 h. The resulting silyloxy compound was then hydrolyzed with aqueous HCl. Then, the mixture was extracted with ether (15 mL × 3), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: hexane/EtOAc = 7/1) to give 1,1,1-trifluoro-11-dodecen-2-ol (2r) (1.77 g, 7.43 mmol, 74%).2r: 1H NMR (CDCl3) δ 1.30-1.38 (m, 12H), 1.53-1.71 (m, 2H), 2.04 (q, J = 7.10 Hz, 2H), 2.32 (br s, 1H), 3.84-3.94 (m, 1H), 4.93 (dm, J = 9.99 Hz, 1H), 4.99 (ddt, J = 16.78, 1.40, 1.40 Hz, 1H), 5.81 (ddt, J = 16.78, 9.99, 6.39 Hz, 1H); 13C NMR (CDCl3) δ 25.23, 29.22, 29.40, 29.52, 29.67, 29.68, 29.90, 70.86 (q, J = 30.86 Hz), 114.48, 125.56 (q, J = 281.02 Hz), 126.96, 139.53; 19F NMR (CDCl3, CFCl3) δ -80.55 (d, J = 7.10 Hz, 3F); IR (neat) 3376, 3078, 2928, 2857, 1641, 1466, 1392, 1279, 1172, 994, 910, 847, 723, 695 cm-1; HRMS (EI) Calcd for (M+) C12H21F3O 238.1544, Found 238.1544.

Reference： [1]Location in patent: experimental part Tanaka, Yusuke; Ishihara, Takashi; Konno, Tsutomu [Journal of Fluorine Chemistry, 2012, vol. 137, p. 99 - 104]

27
[ 112-45-8 ]
[ 112-38-9 ]
[ 51642-06-9 ]
[ 24835-08-3 ]
[ 1377903-66-6 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 5767 - 5776

28
[ 112-45-8 ]
[ 112-38-9 ]
[ 24835-08-3 ]
2-nitrobenzyl isocyanide [ No CAS ]
[ 1377903-67-7 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 5767 - 5776

29
[ 112-45-8 ]
[ 105-34-0 ]
methyl 2-amino-5-(non-8-en-1-yl)thiophene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sulfur; triethylamine In methanol for 15h; Reflux;	Methyl 2-amino-5-(non-8-enyl)thiophene-3-carboxylate (TJ110). Methyl 2-amino-5-(non-8-enyl)thiophene-3-carboxylate (TJ110). To a mixture of undec-10-enal (0.326 g, 1 .95 mmol), methyl cyanoacetate (0.192 g, 1.95 mmol) and sulfur (0.062g, 1.95 mmol) in methanol (10 mL), NEt3(0.196 g, 1.95 mmol) was added. After stirring the resulting mixture at reflux for 15 hrs, the reaction mixture was added to water (20 mL). Ethyl acetate (20 mL) was added and the organic solution was washed with distilled water (3 x20 mL), dried over MgS04, filtered, and then evaporated to dryness to afford the crude product mixture. Purification by column chromatography (silica, eluent heptane - ethyl acetate 50-50) afforded TJ110 (0.465 g, 85%) as an off-white solid. 1H NMR (300 MHz, CDCI3) δΗ 1.30 (m, 8H); 1.58 (m, 2H); 2.04 (q, 2H); 2.56 (t, 2H); 3.78 (s, 3H); 5.49 (m, 2H); 5.79 (m, 3H); 6.60(s, 1 H).
85%	With sulfur; triethylamine In methanol for 15h; Reflux;	6 Methyl 2-amino-5-(non-8-enyl)thiophene-3-carboxylate To a mixture of undec-10-enal (0.326 g, 1.95 mmol), methyl cyanoacetate (0.192 g, 1.95 mmol) and sulfur (0.062 g, 1.95 mmol) in methanol (10 mL), NEt3(0.196 g, 1.95 mmol) was added. After stirring the resulting mixture at reflux for 15 hrs, the reaction mixture was added to water (20 mL). Ethyl acetate (20 mL) was added and the organic solution was washed with distilled water (3×20 mL), dried over MgSO4, filtered, and then evaporated to dryness to afford the crude product mixture. Purification by column chromatography (silica, eluent heptane-ethyl acetate 50-50) afforded TJ110 (0.465 g, 85%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δH 1.30 (m, 8H); 1.58 (m, 2H); 2.04 (q, 2H); 2.56 (t, 2H); 3.78 (s, 3H); 5.49 (m, 2H); 5.79 (m, 3H); 6.60 (s, 1H).
85%	With sulfur; triethylamine for 12h; Reflux; Inert atmosphere;	5.1.2.1. General procedure for the synthesis of 2-amino-5-alkylthiophene-3-carboxylate derivatives 3 as shown in Table 1 General procedure: A solution of aliphatic carbonyl compound 1 (2 mmol), activatednitrile (2 mol), elemental sulfur (2 mmol) and triethylamine(2 mmol) in MeOH (15 ml) was heated at reflux temperature for12 h under argon atmosphere. The MeOH was evaporated underreduced pressure and the residue was extracted with dichloromethane(3 50ml). The combined organic phases were washedwith a saturated solution of NaHCO3, dried over magnesium sulfateand the solvent was evaporated under reduced pressure. Purificationby column chromatography (silica, eluent CH2Cl2) afforded 3 asan off-white solid or a semi-solid.

Reference： [1]Current Patent Assignee: KATHOLIEKE UNIVERSITEIT LEUVEN - WO2013/190137, 2013, A2 Location in patent: Page/Page column 72
[2]Current Patent Assignee: KATHOLIEKE UNIVERSITEIT LEUVEN - US2015/126559, 2015, A1 Location in patent: Paragraph 0376
[3]Thomas, Joice; Jecic, Alenka; Vanstreels, Els; van Berckelaer, Lizette; Romagnoli, Romeo; Dehaen, Wim; Liekens, Sandra; Balzarini, Jan [European Journal of Medicinal Chemistry, 2017, vol. 132, p. 219 - 235]

30
[ 112-45-8 ]
[ 150-13-0 ]
[ 73780-75-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium cyanoborohydride In ethanol at 25℃; for 18h; Inert atmosphere;	4-Undec-10-enylamino-benzoic acid (3). To a solution of 10-undecenal (13) (1.2 mmol) and 4-aminobenzoic acid (4) (1.4 mmol) in 3 mL of ethanol under argon was added NaCNBH3 (3.0 mmol) intwo portions, and the solution was stirred at 25 °C for 18 h. The reaction solution was diluted with diethyl ether, washed with water twice and brine, dried (MgSO4), filtered and concentrated to yield a crude solid that was purified by column chromatography on silica gel using a mixture of hexane and ethyl acetate (9:1) to give 0.24 g (66% yield) of compound 3 as a white solid: mp, 115 - 118 °C; IR ν 13417, 3097, 3065, 2920, 2850, 1652, 1599, 1528, 1469, 1407, 1372, 1308, 1165, 1129, 945, 769, 819, 722, 699; 1H NMR δ 7.93 (d, J = 9.0 Hz, 2H), 6.55 (d, J = 9.0 Hz, 2H), 5.82 (ddt, J = 17.0, 10.3, 6.6Hz, 1H), 4.91 - 5.04 (m, 2H), 3.16 (t, J = 7.2 Hz, 2H, CH2N), 2.01 - 2.09 (m, 2H), 1.63 (quin, J = 7.2 Hz, 2H), 1.36 - 1.41 (m, 2H), 1.27 - 1.34 (m, 10H); 13C NMR δ 172.6, 152.7, 139.1, 132.3, 116.9, 114.1, 111.2, 43.3, 33.8, 29.5, 29.4, 29.3, 29.2, 29.1, 28.9, 27.0; MS (negative mode), m/z calcd for C18H26NO2 (M-H)- 288.2, found 288.3.

Reference： [1]Prior, Allan M.; Zhang, Man; Blakeman, Nina; Datta, Palika; Pham, Hung; Chen, Qian; Young, Lindon H.; Weis, Margaret T.; Hua, Duy H. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1057 - 1061]

31
[ 112-45-8 ]
[ 65-49-6 ]
[ 1560910-92-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium cyanoborohydride In ethanol at 25℃; for 18h; Inert atmosphere;	2-Hydroxy-4-undec-10-enylamino-benzoic acid (4). To a solution of 10-undecenal (13) (1.2 mmol) and 4-amino-2-hydroxybenzoic acid (15) (1.4 mmol) in 3 mL of ethanol under argon, was added NaCNBH3 (3.0 mmol) in two portions, and the resulting solution was stirred at 25 °C for 18 h. The reaction solution was diluted with diethyl ether, washed twice with water and brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a mixture of hexane and ethyl acetate (9:1) as an eluent to yield 0.18 g (50% yield) of compound 4: 1H NMR δ 10.71 (br. s., 1H), 7.66 (d, J = 8.1 Hz, 1H), 6.10 (dd, J = 8.1, 2.3 Hz, 1H), 6.05 (d, J = 2.3 Hz, 1H), 5.74 - 5.87 (m, 1H), 4.90 - 5.03 (m, 2H), 3.14 (t, J = 7.0 Hz, 2H), 1.99 - 2.08 (m, 2H), 1.62 (quin, J = 7.2 Hz, 2H), 1.34 - 1.41 (m, 2H), 1.22 - 1.33 (m, 10H); 13C NMR δ 174.8, 164.7, 155.6, 139.4, 132.4, 114.4, 106.3, 100.5, 97.5, 43.4, 34.0, 29.7, 29.6, 29.5, 29.4, 29.3, 29.1, 27.2; MS (negative mode), m/z calcd for C18H26NO3 (M-H)- 304.2, found 304.6.

Reference： [1]Prior, Allan M.; Zhang, Man; Blakeman, Nina; Datta, Palika; Pham, Hung; Chen, Qian; Young, Lindon H.; Weis, Margaret T.; Hua, Duy H. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1057 - 1061]

32
[ 112-45-8 ]
[ 149051-24-1 ]
[ 1618680-46-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: ω-bromononanyl dimethyl-tert-butylsilyl ether With magnesium In diethyl ether; ethylene dibromide for 5h; Reflux; Stage #2: 10-Undecenal In diethyl ether; ethylene dibromide at 0 - 30℃;	1-((tert-Butyldimethylsilyl)oxy)icos-19-en-10-ol (4) In a flame-dried three necked flask equipped with a 100 mL addition funnel and a condenser, freshly ground magnesium turnings (31.8 g, 1.308 mol) and dry diethyl ether (240 mL) were added. A few drops of1,2-dibromoethane were added to increase the magnesium surface area and the suspension was allowed to stir for 50 minutes at room temperature. Compound 2 (88.2 g, 261.5 mmol) was subsequently added dropwise at a rate that maintained a slight reflux. After the addition, the solution was refluxed for 5 hours. The Grignard reagent was cooled to room temperature and added dropwise to an undec-10-enal (40.0 g, 237.7 mmol) solution in diethyl ether (400 mL) at0 °C. The resulting solution was allowed to warm slowly to room temperature and was subsequently heated at 30 °C for 4 hours. The reaction was quenched at 0 °C with a saturated solution of ammonium chloride. The biphasic mixture was extracted with Et2O. The organic fractions were washed with brine and dried over anhydrous MgSO4. The solvent was removed invacuo to afford a yellow oil. The crude product was purified by column chromatography using hexanes/ethyl acetate (95:5) as eluent affording 97.2 g of 4 as a white solid (96%). Melting point:36-37.5 °C; 1H NMR (300 MHz, Chloroform-d) δ (ppm) 5.82 (ddt, J = 17.1, 10.3, 6.7 Hz, 1H),5.05-4.90 (m, 2H), 3.60 (m, 3H), 2.09-1.99 (m, 2H), 1.72-1.20 (m, 30H), 0.90 (s, 9H), 0.05 (s,6H); 13C NMR (75 MHz, Chloroform-d) δ (ppm) 139.4, 114.3, 72.2, 63.6, 37.7, 34.0, 33.1, 29.92,29.86, 29.80, 29.72, 29.66, 29.34, 29.15, 26.29, 26.24, 26.22, 26.02, 25.88, 18.6, -5.0; IR υmax=3337, 3082, 2922, 2849, 1647, 1475 cm-1; DART/HRMS: [M+H]+ calculated for C26H54O2Si: 427.3966, found: 427.3976; Elemental analysis: calculated: C 73.17%, H 12.75%, found: C73.46%, H 13.00%.

Reference： [1]Sauty, Nicolas F.; Li, Hong; Da Silva, Lucas Caire; Wagener, Kenneth B. [Synthetic Communications, 2014, vol. 44, # 16, p. 2409 - 2415]

33
[ 887144-97-0 ]
[ 7677-24-9 ]
[ 112-45-8 ]
11-oxo-2-(2,2,2-trifluoroethyl)undecanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)CuBr In acetonitrile at 20℃; for 0.5h; Inert atmosphere;	1 4.3 Typical procedure for cyanotrifluoromethylation of alkenes General procedure: General procedure B: To a dried glass tube, Togni reagent 2 (99mg, 0.3mmol, 1.5equiv), (L3)CuBr (10mg, 0.02mmol, 0.1equiv) and CH3CN (1.0mL) were added under N2 atmosphere, followed by substrate 1 (0.2mmol, 1.0equiv) and TMSCN (54μL, 0.4mmol, 2.0equiv). After the reaction mixture was stirred at room temperature for 0.5h, the mixture was concentrated under vacuum. The residue was purified by column chromatography on silica gel with a gradient eluent of petroleum ether and ethyl acetate to afford the product. General procedure B: Pale yellow liquid; 42.7mg, 81%; 1H NMR (400MHz, CDCl3): δ 9.75 (s, 1H), 2.87-2.80 (m, 1H), 2.60-2.46 (m, 1H), 2.42 (t, J=7.2Hz, 2H), 2.36-2.26 (m, 1H), 1.74-1.52 (m, 5H), 1.40-1.26 (m, 9H); 13C NMR (100MHz, CDCl3): δ 202.9, 125.1 (q, J=275.8Hz), 119.7, 43.8, 36.3 (q, J=29.8Hz), 32.0, 29.1, 29.0, 28.9, 28.7, 26.6, 25.5 (q, J=3.0Hz), 21.9; 19F NMR (376MHz, CDCl3): δ -65.0 (t, J=9.4Hz); HRMS (ESI), m/z: calcd. for C13H18F3NO 261.1340 [M-2H]+, found 261.1337.

Reference： [1]Liang, Zhaoli; Wang, Fei; Chen, Pinhong; Liu, Guosheng [Journal of Fluorine Chemistry, 2014, vol. 167, p. 55 - 60]

34
[ 75-61-6 ]
[ 112-45-8 ]
12-bromo-12,12-difluorododecanal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: dibromodifluoromethane; 10-Undecenal With tetrahydrofuran; eosin at 20℃; for 5h; Irradiation; Inert atmosphere; Schlenk technique; Stage #2: With potassium hydrogencarbonate for 5h; Inert atmosphere; Irradiation; Cooling with ice; Schlenk technique;
78%	With eosin y In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;	5 In 25 ml reaction tube add catalyst (16.2 mg, 0 . 025mmol, 5 µM %), (84 mg, 0 . 5mmol, 1.0 equiv.) and THF (15 ml), sealed by a rubber plug, and the 3M adhesive tape seal, then adding CF2Br2(630 mg, 6.0 equiv. , 3.0mmol), liquid nitrogen freezing, oil pump pumping the oxygen, nitrogen, thawing, so cycle three times. The final blue LED lamp is placed at a distance of 2 cm at, room temperature reaction 10h. After the reaction, the solvent is removed under reduced pressure directly, the obtained crude product by column chromatography (hexane: ethyl acetate=20:1), to obtain the product (116 mg), yield: 78%.

Reference： [1]Lin, Qing-Yu; Xu, Xiu-Hua; Qing, Feng-Ling [Organic and Biomolecular Chemistry, 2015, vol. 13, # 32, p. 8740 - 8749]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104892350, 2017, B Location in patent: Paragraph 0060-0061

35
[ 5153-67-3 ]
[ 112-45-8 ]
[ 1262281-23-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 4-nitro-phenol In dichloromethane at 20℃; for 4h; stereoselective reaction;

Reference： [1]Sagamanova, Irina; Rodríguez-Escrich, Carles; Molnár, István Gábor; Sayalero, Sonia; Gilmour, Ryan; Pericàs, Miquel A. [ACS Catalysis, 2015, vol. 5, # 11, p. 6241 - 6248]

36
[ 112-45-8 ]
[ 1275597-05-1 ]
(±)-2-(dec-9-en-1-yl)-6-methoxy-4,4-bis(3-methoxyphenyl)-4H-benzo[d][1,3]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In toluene at 20℃; for 72h; Inert atmosphere;	2.h h) Synthesis of2-(dec-9-en-l-yl)-6-methoxy-4,4-bis(3-methoxyphenyl)-4H- benzo[ d][ l,3]dioxine h) Synthesis of2-(dec-9-en-l-yl)-6-methoxy-4,4-bis(3-methoxyphenyl)-4H- benzo[ d][ l,3]dioxine A mixture of 2-(hydroxybis(3-methoxyphenyl)methyl)-4-methoxyphenol (1.12 g, 3.1 mmol), 10-undecenal (0.37 g, 2.2 mmol) and 4-methylbenzenesulfonic acid hydrate (0.04 g, 0.2 mmol) in toluene (20 mL) was stirred at room temperature for 72 h. The reaction mixture was concentrated. Flash chromatography (Si02, heptane/ethyl acetate 3: 1) gave 1.18 g (quant.) of the target compound. 1H-NMR (500 MHz): 7.24 (t, J = 7.9, 1 H), 7.15 (t, J = 8.0, 1 H), 6.97-6.91 (m, 2 H), 6.91-6.84 (m, 2 H), 6.82 (d, J = 9.0, 1 H), 6.80-6.74 (m, 2 H), 6.73 (dd, J = 9.0, 3.2, 1 H), 6.40 (d, J = 2.9, 1 H), 5.85-5.75 (m, 1 H), 5.02-4.89 (m, 3 H), 3.74 (s, 3 H), 3.72 (s, 3 H), 3.63 (s, 3 H), 2.06-1.99 (m, 2 H), 1.91-1.75 (m, 2 H), 1.54-1.31 (m, 4 H), 1.31-1.10 (m, 8 H). 13C-NMR (125.8 MHz): 159.37, 159.19, 152.78, 147.48, 146.53, 145.83, 139.21, 128.87, 128.72, 125.76, 121.79, 120.76, 117.50, 114.91, 114.82, 114.26, 114.12, 114.10, 113.38, 112.51, 95.23, 83.99, 55.59, 55.20, 55.14, 34.51, 33.79, 29.47, 29.37, 29.35, 29.10, 28.91, 23.55.
100%	With toluene-4-sulfonic acid In toluene at 20℃; for 72h; Inert atmosphere;

Reference： [1]Current Patent Assignee: Firmenich International SA - WO2016/116420, 2016, A1 Location in patent: Page/Page column 23
[2]Trachsel, Alain; Buchs, Barbara; Herrmann, Andreas [Photochemical and Photobiological Sciences, 2016, vol. 15, # 9, p. 1183 - 1203]

37
[ 112-45-8 ]
2-(hydroxybis(3-(methylthio)phenyl)methyl)-4-methoxyphenol [ No CAS ]
(±)-2-(dec-9-en-1-yl)-6-methoxy-4,4-bis(3-(methylthio)phenyl)-4H-benzo[d][1,3]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With toluene-4-sulfonic acid In cyclohexane for 2h; Inert atmosphere; Reflux;	2.i i) Synthesis of2-( dec-9-en-l -yl)-6-methoxy-4,4-bis( 3-( methylthio )phenyl)-4H- benzo[ d][ l,3]dioxine i) Synthesis of2-( dec-9-en-l -yl)-6-methoxy-4,4-bis( 3-( methylthio )phenyl)-4H- benzo[ d][ l,3]dioxine A mixture of 2-(hydroxybis(3-(methylthio)phenyl)methyl)-4-methoxyphenol (1.0 g, 2.5 mmol), 10-undecenal (0.42 g, 2.5 mmol) and 4-methylbenzenesulfonic acid hydrate (0.05 g, 0.3 mmol) in cyclohexane (20 mL) was stirred under reflux with azeotropic removal of water for 2 h. The reaction mixture was left cooling to room temperature, washed with a saturated aqueous solution of NaHC03 (50 mL), dried (Na2S04) and concentrated. Flash chromatography (Si02, heptane/ethyl acetate 9: 1) gave 0.87 g (63%) of the target compound. 1H-NMR (500 MHz): 7.29-7.08 (m, 7 H), 6.95-6.90 (m, 1 H), 6.83 (d, J = 9.0, 1 H), 6.75 (dd, J = 9.0, 2.9, 1 H), 6.36 (d, J = 6.9, 1 H), 5.85-5.75 (m, 1 H), 5.02-4.88 (m, 3 H), 3.64 (s, 3 H), 2.41 (s, 3 H), 2.39 (s, 3 H), 2.06-1.99 (m, 2 H), 1.89-1.74 (m, 2 H), 1.52-1.31 (m, 4 H), 1.31-1.17 (m, 8 H). 13C-NMR (125.8 MHz): 152.86, 146.56, 146.49, 144.82, 139.21, 138.60, 138.16, 128.40, 128.26, 126.84, 126.14, 125.99, 125.88, 125.56, 125.28, 125.12, 117.67, 114.90, 114.23, 114.11, 95.21, 83.84, 55.63, 34.45, 33.80, 29.47, 29.37, 29.34, 29.10, 28.91, 23.52, 15.77, 15.63.
63%	With toluene-4-sulfonic acid In cyclohexane for 2h; Reflux; Dean-Stark; Inert atmosphere;

Reference： [1]Current Patent Assignee: Firmenich International SA - WO2016/116420, 2016, A1 Location in patent: Page/Page column 23-24
[2]Trachsel, Alain; Buchs, Barbara; Herrmann, Andreas [Photochemical and Photobiological Sciences, 2016, vol. 15, # 9, p. 1183 - 1203]

38
[ 112-45-8 ]
[ 6326-60-9 ]
(±)-2-(dec-9-en-1-yl)-4,4-diphenyl-4H-benzo[d][1,3]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With toluene-4-sulfonic acid In toluene at 20℃; for 18h; Inert atmosphere;	3.a Synthesis of( ±)-2-(dec-9-en-l-yl)-4,4-diphenyl-4H-benzo[d][l,3]dioxine Synthesis of( ±)-2-(dec-9-en-l-yl)-4,4-diphenyl-4H-benzo[d][l,3]dioxine A mixture of 2-(hydroxydiphenylmethyl)phenol (0.50 g, 1.8 mmol), 10-undecenal (0.20 g, 1.2 mmol) and 4-methylbenzenesulfonic acid hydrate (0.02 g, 0.1 mmol) in toluene (10 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated. Flash chromatography (Si02, heptane/ethyl acetate 7: 1) gave 0.52 g (quant.) of the target compound. 1H-NMR (500 MHz): 7.37-7.31 (m, 5 H), 7.27-7.19 (m, 5 H), 7.18-7.12 (m, 1 H), 6.92-6.88 (m, 1 H), 6.84-6.79 (m, 2 H), 5.86-5.75 (m, 1 H), 5.02-4.95 (m, 2 H), 4.95-4.89 (m, 1 H), 2.07-1.99 (m, 2 H), 1.91-1.77 (m, 2 H), 1.52-1.31 (m, 4 H), 1.31-1.15 (m, 8 H). 13C-NMR (125.8 MHz): 152.49 (s), 146.22 (s), 144.32 (s), 139.22 (d), 129.83 (d), 129.27 (d), 128.27 (d), 128.19 (d), 128.00 (d), 127.92 (d), 127.79 (d), 127.42 (d), 125.44 (s), 120.03 (d), 117.02 (d), 114.11 (t), 95.23 (d), 84.11 (s), 34.48 (t), 33.79 (t), 29.44 (t), 29.36 (t), 29.30 (t), 29.09 (t), 28.90 (t), 23.40 (t).
100%	With toluene-4-sulfonic acid In toluene at 20℃; for 18h; Inert atmosphere;

Reference： [1]Current Patent Assignee: Firmenich International SA - WO2016/116420, 2016, A1 Location in patent: Page/Page column 25
[2]Trachsel, Alain; Buchs, Barbara; Herrmann, Andreas [Photochemical and Photobiological Sciences, 2016, vol. 15, # 9, p. 1183 - 1203]

39
[ 112-45-8 ]
2-(hydroxydiphenylmethyl)-6-methoxyphenol [ No CAS ]
(±)-2-(9-decenyl)-8-methoxy-4,4-diphenyl-4Hbenzo[d][1,3]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With toluene-4-sulfonic acid In toluene at 20℃; for 72h; Inert atmosphere;	3.b Synthesis of 2-(9-decenyl)-8-methoxy-4,4-diphenyl-4H-benzo[d] [1 ,3] dioxine Synthesis of 2-(9-decenyl)-8-methoxy-4,4-diphenyl-4H-benzo[d] [1 ,3] dioxine A mixture of 2-(hydroxydiphenylmethyl)-6-methoxyphenol (1.00 g, 3.3 mmol), 10-undecenal (0.37 g, 2.2 mmol) and 4-methylbenzenesulfonic acid hydrate (0.04 g, 0.2 mmol) in toluene (11 mL) was stirred at room temperature for 72 h. The reaction mixture was concentrated. Flash chromatography (Si02, heptane/ethyl acetate 7: 1, then ethyl acetate) gave 0.97 g (97%) of the target compound. 1H-NMR: 7.39-7.30 (m, 5 H), 7.28-7.18 (m, 5 H), 6.79-6.72 (m, 2 H), 6.46-6.39 (m, 1 H), 5.86-5.74 (m, 1 H), 5.03-4.89 (m, 3 H), 3.89 (s, 3 H), 2.06-1.98 (m, 2 H), 1.98-1.85 (m, 2 H), 1.53-1.41 (m, 1 H), 1.41-1.30 (m, 3 H), 1.30-1.12 (m, 8 H). 13C-NMR: 148.22, 146.17, 144.28, 142.44, 139.24, 129.37, 128.24, 127.95, 127.78, 127.42, 126.13, 121.73, 119.35, 114.10, 109.79, 95.61, 84.06, 55.99, 34.43, 33.79, 29.42, 29.36, 29.21, 29.09, 28.90, 23.54
95%	With toluene-4-sulfonic acid In toluene at 20℃; for 72h; Inert atmosphere;

Reference： [1]Current Patent Assignee: Firmenich International SA - WO2016/116420, 2016, A1 Location in patent: Page/Page column 25-26
[2]Trachsel, Alain; Buchs, Barbara; Herrmann, Andreas [Photochemical and Photobiological Sciences, 2016, vol. 15, # 9, p. 1183 - 1203]

40
[ 936716-83-5 ]
[ 112-45-8 ]
(±)-2-(9-decenyl)-6-methoxy-4,4-diphenyl-4H-benzo[d][1,3]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With toluene-4-sulfonic acid In toluene at 20℃; for 72h; Inert atmosphere;	3.c Synthesis of( ±)-2-( 9-decenyl)-6-methoxy-4,4-diphenyl-4H-benzo[ d][ l,3]dioxine Synthesis of( ±)-2-( 9-decenyl)-6-methoxy-4,4-diphenyl-4H-benzo[ d][ l,3]dioxine A mixture of 2-(hydroxydiphenylmethyl)-4-methoxyphenol (1.00 g, 3.3 mmol), 10-undecenal (0.37 g, 2.2 mmol) and 4-methylbenzenesulfonic acid hydrate (0.04 g, 0.2 mmol) in toluene (11 mL) was stirred at room temperature for 72 h. The reaction mixture was concentrated. Flash chromatography (Si02, heptane/ethyl acetate 7: 1) gave 1.01 g (quant.) of the target compound. 1H-NMR: 7.39-7.30 (m, 5 H), 7.27-7.17 (m, 5 H), 6.84 (d, 1 H), 6.74 (dd, 1 H), 6.36 (d, 1 H), 5.85-5.75 (m, 1 H), 5.01-4.95 (m, 1 H), 4.95-4.90 (m, 2 H), 3.62 (s, 3 H), 2.06-1.99 (m, 2 H), 1.89-1.74 (m, 2 H), 1.52-1.31 (m, 4 H), 1.31-1.13 (m, 8 H). 13, C-NMR: 152.77, 146.65, 146.13, 144.30, 139.21, 129.23, 128.11, 127.98, 127.92, 127.84, 127.43, 125.92, 117.55, 115.03, 114.11, 114.02, 95.16, 84.12, 55.56, 34.46, 33.79, 29.43, 29.36, 29.29, 29.09, 28.90, 23.44.
100%	With toluene-4-sulfonic acid In toluene at 20℃; for 72h; Inert atmosphere;

Reference： [1]Current Patent Assignee: Firmenich International SA - WO2016/116420, 2016, A1 Location in patent: Page/Page column 26-27
[2]Trachsel, Alain; Buchs, Barbara; Herrmann, Andreas [Photochemical and Photobiological Sciences, 2016, vol. 15, # 9, p. 1183 - 1203]

41
[ 112-45-8 ]
[ 7188-38-7 ]
[ 941172-00-5 ]
C₃₂H₄₇N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99.7%	With toluene-4-sulfonic acid In dichloromethane; dimethyl sulfoxide at 20℃; for 80h;	Passerini product 23 derived from Biginelli acid 15, undec-10-enal and tert-butylisocyanide In a 5 mL round-bottomed flask, finely powdered Biginelli acid 15 (500 mg, 1.57 mmol, 1.20equiv) was dissolved in 1 mL dimethyl sulfoxide/dichloromethane (1:1). Subsequently, undec-10-enal (344 mg, 2.04 mmol, 409 µL, 1.30 equiv) and tert-butylisocyanide (170 mg, 2.04 mmol,196 µL) were added. The mixture was diluted with dichloromethane (0.5 mL) and stirred atroom temperature for 8 h. Subsequently, a second portion of aldehyde (79.3 mg, 0.30 equiv)and ioscyanide (39.2 mg, 0.30 equiv) were added to the mixture and stirred at roomtemperature for 3 d. The crude reaction mixture was added dropwise into a stirred emulsion of50 mL water and 50 mL dichloromethane. The organic phase was separated, dried oversodium sulfate and dried under reduced pressure. The oily residue was purified via column chromatography on silica gel eluting with a gradual solvent mixture of c-hexane and diethylether (0:1 1:0). The Passerini product 23 was obtained as a colorless oil (893 mg, 1.56mmol, 99.7%).IR (ATR): [cm-1] = 3323.2 (br, (N-H)), 2924.7 (m, (C-H)), 2853.1 (w, (C-H)), 1752.5(w (C=O)), 1681.5 (vs, (C=O)), 1529.2 (m), 1453.7 (m), 1385.8 (m), 1364.8 (m), 1309.4 (w),1278.1 (w), 1257.7 (w), 1176.3 (vs), 1103.6 (s), 1056.2 (m), 941.7 (w), 909.0 (w), 861.3 (w),828.5 (w), 759.6 (m), 697.5 (s), 651.6 (w).1H NMR (400 MHz, DMSO-d6): δ [ppm] = 8.16 (dd, J = 16.9, 3.6 Hz, 1 H, NH3), 7.43 (d, J =11.2 Hz, 1 H, NH28), 7.34 - 7.21 (m, 5 H, CHAr10-14), 5.84 - 5.73 (m, 1 H, CH34), 5.19 (t, J = 3.5Hz, 1 H, CH2), 5.02 - 4.91 (m, 2 H, CH233), 4.84 (t, J = 6.3 Hz, 1 H, CH23), 4.74 - 4.40 (m, 2 H,CH220), 4.06 - 3.96 (m, 2 H, CH217), 2.43 (d, J = 17.4 Hz, 3 H, CH39), 2.00 (q, J = 6.9 Hz, 2 H,CH235), 1.69 - 1.61 (m, 2 H, CH242), 1.27 - 1.21 (m, 21 H, CH329,31,32 + CH236-41), 1.14 - 1.07 (t,J = 7.1 Hz, 3 H, CH319).13C NMR (100 MHz, DMSO-d6): δ [ppm] = 168.95 (s, CO2R21),), 168.88 (s, CO2R21),), 168.14(s, CONR24), 165.43 (s, CO2R16), 165.41 (s, CO2R16), 152.49 (s, CO4), 152.27 (s, CO4), 148.84(s, C6), 148.76 (s, C6), 144.05 (s, CAr8), 143.87 (s, CAr8), 138.79 (s, CH34), 128.38 (s, CHAr10,14),128.34 (s, CHAr10,14), 127.41 (s, CHAr12), 126.49 (s, CHAr11,13), 126.38 (s, CHAr11,13), 114.60 (s,CH233), 103.21 (s, C1), 103.19 (s, C1), 74.31 (s, CH23), 74.16 (s, CH23), 59.65 (s, CH217), 53.15(s, CH2), 52.95 (s, CH2), 50.30 (s, C26), 50.26 (s, C26), 44.03 (s, CH220), 33.17 (s, CH235), 31.37(s, CH242), 31.28 (s, CH242), 28.79 (s, CH2), 28.75 (s, CH2), 28.65 (s, CH2), 28.54 (s, CH2),28.51 (s, CH2), 28.45 (s), 28.34 (s, CH329,31,32), 28.24 (s, CH241), 26.32 (s, CH241), 24.31(s,CH2), 24.27 (s, CH241), 15.53 (s, CH39), 15.48 (s, CH39), 13.93 (s, CH319).FAB - MS [m/z] (relative intensity): 570.4 (55%) [M + H]+, 524.3 (35%) [M - C2H5O]+, 492.3(10%) [M - C6H5]+, 317.1 (65%) [Fragment A]+, 273.1 (35%) [Fragment B]+.HRMS - FAB [m/z]: [M + H]+ calculated for 12C321H4816O614N3, 570.3538; found, 570.3538; Δ =0.04 mmu.

Reference： [1]Boukis, Andreas C.; Monney, Baptiste; Meier, Michael A. R. [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 54 - 62]

42
[ 112-45-8 ]
[ 120446-58-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With titanium tetrachloride; zinc In 1,4-dioxane for 2h; Sonication; Cooling;	1.A 8.0 g (122 mmol) of zinc powder and 150 mL of 1,4-dioxane were placed in a three-necked flask (300 mL), cooled with ice / salt with stirring, and 10.6 g (55.9 mmol ) titanium tetrachloride was slowly added dropwise. After completion of the dropwise addition, 6.23 g (37.0 mmol) of 10-undecenal was added by a syringe and stirred while irradiating with ultrasonic wave for 2 hours. Thereafter, 200 mL of 1N hydrochloric acid and 150 mL of diethyl ether were added and stirred, and then the mixture was filtered through celite to remove residual zinc powder. The organic layer of the filtrate was washed with an aqueous solution of ammonium chloride and saturated brine, concentrated under reduced pressure, and recrystallized in hexane to obtain 8.4 g (yield 77%) of compound (I-1).
1 g	With methanol; samarium diiodide In tetrahydrofuran at 20℃; for 2h;	6 Example 6 A mixture of 10-undecenal (1.1 g), tetrahydrofuran (THF) (100 mL), methanol (1 mL), and a 0.1 M solution of samarium iodide (90 mL) were stirred at room temperature for two hours. Then, 100 mL of a hydrochloric acid (1 M) solution was added thereto and the mixture was extracted with diethyl ether. Then, the solvent was distilled off and the residue was purified by column chromatography, whereby docosa-1,21-diene-11,12-diol (1.0 g) was obtained. The resulting docosa-1,21-diene-11,12-diol showed the following spectrum data. 1H-NMR (CDCl3) δ ppm: 1.08 (J=6.8, m, 10H), 1.32 (m, 2H), 1.45 (m, 2H), 1.98 (s, 3H), 2.33 (J=7.6, t, 2H), 3.83 (J=6.5, t, 2H)

Reference： [1]Current Patent Assignee: NEOS COMPANY LIMITED - JP6091963, 2017, B2 Location in patent: Paragraph 0051; 0052
[2]Current Patent Assignee: DAIKIN INDUSTRIES LIMITED - US2020/24222, 2020, A1 Location in patent: Paragraph 0392-0394

43
[ 112-45-8 ]
[ 17814-85-6 ]
(Z)-hexadeca-5,15-dienoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 10-Undecenal In tetrahydrofuran at 0 - 20℃; for 17h; Inert atmosphere;	General procedure B: Wittig Reaction General procedure: Under an atmosphere of argon, the carboxyalkyl triphenyl phosphonium bromide (2.0 equiv) is dissolved in anhydrous THF (0.6 M) The suspension is cooled to 0 °C and KOt-Bu (powder or 1 M in THF; 4.0 equiv) is added dropwise. After 30 min of stirring at room temperature, a solution of the aldehyde (1.0 equiv) in anhydrous THF (2 M) is added dropwise at 0 °C. The reaction is stirred at room temperature and after the aldehyde is consumed, the mixture is quenched with 1 M aq. HCl solution (20 mL), extracted with Et2O (3 30 mL) and washed with H2O (2 60 mL). The combined organic layers are washed with brine, dried over anhydrous Na2SO4, filtered and the solvent is removed under reduced pressure. The residue is purified on silica gel to yield the title compound.

Reference： [1]Rode, Katharina; Palomba, Martina; Ortgies, Stefan; Rieger, Rene; Breder, Alexander [Synthesis, 2018, vol. 50, # 19, p. 3875 - 3885]

44
[ 112-45-8 ]
[ 77485-00-8 ]
C₃₅H₃₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With indium(III) chloride In dichloromethane at 20℃; for 52h;	Synthesis of compound 11 To asolution of 91 (211 mg, 1.15 mmol) in CH2Cl2(12.0 mL, 0.05 M), were added 10-udecenal (97 mg, 0.577 mmol) and InCl3(13 mg, 0.058 mmol). After the mixture was stirred at room temperature for 52hours, powder of NaOH (70 mg, 2.50 mmol) was added. After the mixture was stirredfor 30 min, a pale yellow material was precipitated which was removed byfiltration through a cotton plug. The solvent was evaporated to give a residuethat was purified by flash column chromatography (SiO2,hexane/EtOAc). 11 was obtained as a darkblue oil (258 mg, 68%).1H NMR: δ 7.72 (d, J = 8.4 Hz,4H), 7.39 (t, J = 8.0 Hz, 4H), 7.24(m, 4H), 6.61 (s, 2H), 6.15 (s, 2H), 5.88 (m, 1H). 5.01 (dd, J = 17.6 Hz, 10.0 Hz, 2H), 4.02 (t, J = 7.6 Hz, 1H), 2.08 (m, 2H), 1.91 (m,2H), 1.22 (br, 12H); 13C NMR: δ 154.9, 148.4, 139.3, 136.6, 132.2, 128.8, 126.7, 125.5, 123.2, 114.3,94.4, 90.5, 40.1, 34.4, 33.9, 29.6, 29.2, 29.0, 27.7. HRMS (ESI): m/z calcd for C35H36O2N2Na1[M+Na]+ 539.26745, found 539.26718; IR (ATR): 3427, 2926, 2853, 1603, 1486, 1370 cm-1

Reference： [1]Wang, Yabin; Kasahara, Junya; Yamagata, Kazuyuki; Nakamura, Hiroyuki; Murayama, Toshihiko; Suzuki, Noriyuki; Nishida, Atsushi [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 19, p. 3222 - 3226]

45
[ 112-45-8 ]
[ 1283722-06-4 ]
(2S,3R)-N,N-diallyl-3-hydroxy-2-methyltridec-12-enethioamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In tetrahydrofuran at -70℃; for 120h; Inert atmosphere;	General Procedure for the syn-Selective Catalytic AsymmetricAldol Reaction of Thioamide 5 General procedure: A flame-dried test tube (20 mL) equipped with a magnetic stirringbar and a three-way glass stopcock was charged with (S,S)-Ph-BPE (6.1 mg, 0.012 mmol), 2,2,5,7,8-pentamethylchromanol(6, 2.6 mg, 0.012 mmol), and mesitylcopper (2.2 mg, 0.012mmol) in a dry box. To the mixture was added dry THF (240 μL,0.05 M) with a syringe at r.t. After 5 min of stirring at the sametemperature, a yellow-green solution of (S,S)-Ph-BPE/mesitylcopper/6 was obtained, which was used within 15 min. Aflame-dried test tube (20 mL) was charged with N,N-diallylthiopropionamide(4a, 1.2 equiv), dry THF (0.2 M), 1 (1.0 equiv). Thereaction mixture was cooled to -70 °C. To the resulting cooledsolution was added dropwise previously prepared (S,S)-Ph-BPE/mesitylcopper/6 solution (3 mol%) to run the reaction.After a certain time at the same temperature, the precooledsolution of acetic acid in THF (0.1 M in THF, 1 mL), then saturatedNH4Cl aq. were added to quench the reaction. Theaqueous layer was extracted with ethyl acetate. The combinedorganic layers were washed with brine and dried with Na2SO4.The filtrate was concentrated under reduced pressure. Theresidual product was purified by silica gel column chromatography(n-hexane/EtOAc) to give 5.

Reference： [1]Ota, Yuya; Li, Zhao; Kumagai, Naoya; Shibasaki, Masakatsu [Synlett, 2019, vol. 30, # 5, p. 620 - 624]

46
[ 112-45-8 ]
(S)-5-[(tert-butyldiphenylsilyl)oxy]-2-ethyl-1-pentanamine [ No CAS ]
(S)-5-[(tert-butyldiphenylsilyl)oxy]-2-ethyl-N-(10-undecenyl)-1-pentanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium cyanoborohydride; acetic acid In dichloromethane at 20℃; for 12h;	(S)-5-[(tert-Butyldiphenylsilyl)oxy]-2-ethyl-N-(10-undecenyl)-1-pentanamine (10). 10-Undecenal (0.05 mL,0.25 mmol) and AcOH (0.02 mL) were added to a suspension of amine 8 (74 mg, 0.20 mmol) and NaBH3CN (25 mg, 0.40 mmol) in anhydrous CH2Cl2 (2.3 mL), and the mixture was stirred at room temperature for 12 h. Then, water was added, and the mixture was extracted with CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4 and filtered, and the solvent was removed under reduced pressure. Flash chromatography (from 98:2 hexane-EtOAc to EtOAc) of the residue gave secondary amine 10 (30 mg, 29% yield) as a colorless oil: [α]22D -12.3 (c 0.225, MeOH);1H-NMR (400 MHz, CDCl3, COSY, g-HSQC): δ = 0.90 (t, J = 7.4 Hz, 3H, CH3CH2), 1.05 [s, 9H, (CH3)3],1.24-1.58 (m, 18H, 9CH2), 1.65-1.77 (m, 3H, H-2, H-4), 2.01-2.06 (m, 2H, CH2=CHCH2), 2.81-2.84 (m,2H, H-5), 2.88-2.96 (m, 2H, CH2N), 3.66-3.70 (m, 2H, H-1), 4.91-5.01 (m, 2H, CH2=CH), 5.80 (m, 1H,CH2=CH), 7.32-7.55 (m, 6H, ArH), 7.63-7.67 (m, 4H, ArH); 13C-NMR (100.6 MHz, CDCl3): δ = 10.2(CH3CH2), 19.3 [C(CH3)3], 23.1 (CH2), 23.7 (CH2), 25.8 (CH2), 26.7 (CH2), 26.8 (CH2), 27.0 [C(CH3)3], 29.0(CH2), 29.1 (CH2), 29.2 (CH2), 29.4 (CH2), 29.8 (CH2), 33.9 (CH2=CHCH2), 36.3 (C-4), 49.0 (CH2N), 51.6(C-5), 63.8 (C-1), 114.3 (CH2=CH), 127.8 (CH-Ar), 129.8 (CH-Ar), 133.9 (C-Ar), 135.6 (CH-Ar), 139.3(CH2=CH).

Reference： [1]Guignard, Guillaume; Llor, Núria; Pubill, David; Bosch, Joan; Amat, Mercedes [Molecules, 2019, vol. 24, # 6]

47
[ 112-45-8 ]
[ 41128-14-7 ]
3-hydroxy-1-trityl-3-(undec-10-enoyl)indolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With 2-(perfluorophenyl)-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate; sodium hydrogencarbonate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;	Cross-Benzoin Reaction; General Procedure General procedure: To a dry 10 mL Schlenk tube equipped with a magnetic stir bar, were added NHC pre-catalyst D (0.01 mmol), isatin 2 (0.1 mmol), and NaHCO3 (0.1 mmol). The tube was sealed with a septum, evacuated and refilled with N2 (3 cycles). DCE (1 mL) and aldehyde 1 (0.15 mmol)were then added and the reaction mixture was stirred for 24 h at rt. After complete consumption of isatin 2, DCE was removed under reduced pressure and the residue was subjected to column chromatography using PE/EtOAc (9:1 → 5:1) as eluent to afford the desired product 3.

Reference： [1]Ji, Haojie; Xu, Jianfeng; Ren, Hongjun [Synthesis, 2019, vol. 51, # 10, p. 2191 - 2197]

48
[ 64-18-6 ]
[ 112-45-8 ]
[ 3956-80-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium diacetate; acetic anhydride; P(p-C₆H₄F)3 In toluene at 80℃; for 48h; Sealed tube; Inert atmosphere; regioselective reaction;
92%	With palladium diacetate; acetic anhydride; P(p-C₆H₄F)3 In toluene at 80℃; for 48h; Inert atmosphere; Sealed tube;	9 Example 9 Synthesis of 12-aldehyde-dodecanoic acid (Structural Formula 4-i) TFPP stands for monophosphine ligand.Under the protection of argon gas, palladium acetate (0.025 mmol, 0.0056 g), monophosphine ligand TFPP (0.15 mmol, 0.0474 g), 0.5 mL of toluene, and 10-undecene having the structural formula 3-i were sequentially added to the reactor. Aldehyde (0.5 mmol, 0.0841 g), formic acid (0.75 mmol, 0.0345 g) and acetic anhydride (0.1 mmol, 0.0102 g). Screw on the bottle cap to seal and adjust the temperature of the heating plate to 80 ° C. After 48 hours, the heating was stopped, the mixture was cooled to room temperature, and separated by column chromatography (the volume ratio of petroleum ether: ethyl acetate was 10: 1) to obtain 0.098 g of a white solid.12-aldehyde-dodecanoic acid (see structural formula 4-i described in the above reaction formula), yield 92%, linear to branched chain ratio is greater than 100: 1

Reference： [1]Ren, Wenlong; Chu, Jianxiao; Sun, Fei; Shi, Yian [Organic Letters, 2019, vol. 21, # 15, p. 5967 - 5970]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN110423191, 2019, A Location in patent: Paragraph 0071-0074

49
[ 112-45-8 ]
[ 109-73-9 ]
[ 50279-04-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	In methanol at 23℃; for 2h;
66%	Stage #1: 10-Undecenal; N-butylamine In methanol at 23℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 0℃; for 0.5h;	V-Butylundec-10-en-1 -amine (1ad) To a stirred solution of 10-undecenal (505 mg, 3.00 mmol, 1.00 equiv.) in MeOH (3 mL) was added n-butylamine (594 pL, 6.00 mmol, 2.00 equiv.), and the mixture was stirred at ambient temperature (23 °C) for 2 h. After this time, the reaction mixture was cooled to 0 °C and sodium borohydride (57.0 mg, 1.50 mmol, 0.75 equiv.) was added. The resulting mixture was stirred at 0 °C for 30 min, after which excess reductant was quenched by the addition of water (3 mL). The crude mixture was extracted with DCM (3 c 5 mL), the combined organic phases were dried over anhydrous magnesium sulfate and the dried solution was filtered. The filtrate was concentrated under reduced pressure and the resulting crude material was purified by flash column chromatography on silica gel (dichloromethane/MeOH/NH4OH) to afford the title compound. 66% yield; 1H NMR (600 MHz, CDCI3) d 5.81 (ddt, J = 16.9, 10.2, 6.7 Hz, 1 H), 4.99 (dd, J = 17.1 , 1.4 Hz, 1 H), 4.93-4.90 (m, 1 H), 2.67 (ddd, J = 12.7, 8.0, 3.0 Hz, 3H), 2.03 (q, J = 7.0 Hz, 2H), 1.67-1.51 (m, 3H), 1.43-1.20 (m, 15H), 0.92 (t, J = 7.3 Hz, (0360) 3H).

Reference： [1]Kaiser, Daniel; Tona, Veronica; Gonçalves, Carlos R.; Shaaban, Saad; Oppedisano, Alberto; Maulide, Nuno [Angewandte Chemie - International Edition, 2019, vol. 58, # 41, p. 14639 - 14643][Angew. Chem., 2019, vol. 131, # 41, p. 14781 - 14785,5]
[2]Current Patent Assignee: UNIVERSITY OF VIENNA - WO2019/219942, 2019, A1 Location in patent: Page/Page column 63

50
[ 112-45-8 ]
[ 109-89-7 ]
[ 6308-95-8 ]

Yield	Reaction Conditions	Operation in experiment
30%	In methanol at 23℃; for 2h;
30%	Stage #1: 10-Undecenal; diethylamine In methanol at 23℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 0℃; for 0.5h;	A/,/V-Diethylundec-10-en-1 -amine (1ae) To a stirred solution of 10-undecenal (505 mg, 3.00 mmol, 1.00 equiv.) in MeOH (3 mL) was added A/,A/-diethylamine (621 pL, 6.00 mmol, 2.00 equiv.), and the mixture was stirred at ambient temperature (23 °C) for 2 h. After this time, the reaction mixture was cooled to 0 °C and sodium borohydride (57.0 mg, 1.50 mmol, 0.75 equiv.) was added. The resulting mixture was stirred at 0 °C for 30 min, after which excess reductant was quenched by the addition of water (3 mL). The crude mixture was extracted with DCM (3 * 5 mL), the combined organic phases were dried over anhydrous magnesium sulfate and the dried solution was filtered. The filtrate was concentrated under reduced pressure and the resulting crude material was purified by flash column chromatography on silica gel (dichloromethane/MeOH/NH4OH) to afford the title compound. 30% yield. 1H NMR (600 MHz, CDCI3) d 5.81 (ddt, J = 16.9, 10.2, 6.7 Hz, 1 H), 4.99 (ddd, J = 17.1 , 3.6, 1.6 Hz, 1 H), 4.93-4.91 (m, 1 H), 2.51 (q, J = 7.2 Hz, 4H), 2.40-2.38 (m, 2H), 2.05-2.01 (m, 2H), 1.44-1.42 (m, 2H), 1.38-1.36 (m, 2H), 1.27-1.24 (m, 10H), 1.01 (t, J = 7.2 Hz, 6H); 13C NMR (150 MHz, CDCI3) d 139.4, 1 14.2, 53.2, 47.0 (2C), 34.0, 29.8, 29.7, 29.6, 29.3, 29.1 , 27.9, 27.2, 11.8 (2C); IR (neat) vmax: 2968, 2923, 2853, 2797, 1464, 1380, 1202, 1070, 991 , 908; HRMS (ESI+): exact mass calculated for [M+H]+ (C15H32N) requires m/z 226.2529, found m/z 226.2527.

Reference： [1]Kaiser, Daniel; Tona, Veronica; Gonçalves, Carlos R.; Shaaban, Saad; Oppedisano, Alberto; Maulide, Nuno [Angewandte Chemie - International Edition, 2019, vol. 58, # 41, p. 14639 - 14643][Angew. Chem., 2019, vol. 131, # 41, p. 14781 - 14785,5]
[2]Current Patent Assignee: UNIVERSITY OF VIENNA - WO2019/219942, 2019, A1 Location in patent: Page/Page column 63-64

51
[ 112-45-8 ]
[ 4433-30-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diethyl ether / 3 h / 0 - 35 °C / Inert atmosphere 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; cesium acetate / tetrahydrofuran / 15 h / 70 °C / Glovebox; Sealed tube; Inert atmosphere

Reference： [1]Dong, Wenke; Yang, Hongxuan; Yang, Wen; Zhao, Wanxiang [Organic Letters, 2020]

52
[ 112-45-8 ]
[ 1166823-79-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With oxalyl dichloride; 1,1'-sulfinylbisbenzene In dichloromethane at -78 - 20℃; Inert atmosphere; chemoselective reaction;	General procedure for dichlorination of olefins or olefins with hydroxy orcarbonyl group using Ph 2 SO and (COCl) 2 General procedure: To a solution of oxalyl chloride (0.51 mL, 6.0 mmol, 1.2 equiv.) in CH 2 Cl 2 (10 mL)cooled at 78C was added dropwise a solution of diphenyl sulfoxide (1.21 g, 6.0 mmol,1.2 equiv.) in CH 2 Cl 2 (10 mL) under the atmosphere of nitrogen. After 10 min, a solu-tion of substrate (5 mmol, 1.0 equiv.) in CH 2 Cl 2 (10 mL) was added. The mixture wasthen allowed to warm up to the temperature and stirred until TLC showed the reactioncompleted. Distilled water (30 mL) was added dropwise at 0C. After stirring for10 min, the organic layer was separated and successively washed with brine. The com-bined organic extracts were dried (Na 2 SO 4 ), filtered, and concentrated in vacuum. For16, 34, 35, and 37, the residue was purified by flash chromatography (silica gel, petrol-eum ether/ethyl acetate 30:1 for 16, and 10:1 for 34, 35 and 37). For 17, 19, 21, 24,26, 28 and 32, the corresponding dichloroalkanes and the byproduct diphenyl sulfidecannot be separated by chromatography due to the similar polarity. The problem can besolved by oxidizing diphenyl sulfide to diphenyl sulfoxide to differentiate the polarity.The residue was dissolved in CH 3 CN (20 mL), then aqueous 30% H 2 O 2 (1.5 mL,15 mmol, 3.0 equiv.) and TMSCl (0.96 mL, 7.5 mmol, 1.5 equiv.) were added. The mix-ture was stirred at room temperature for 30 min. After the disappearance of diphenylsulfide, the reaction mixture was quenched by adding water (20 mL), extracted withCH 2 Cl 2 (3 20 mL), and the extract washed with brine, dried (Na 2 SO 4 ), filtered, andconcentrated in vacuum. Purification by flash chromatography (silica gel, petroleumether/ethyl acetate 20:1) afforded the corresponding dichloroalkanes.

Reference： [1]Ding, Rui; Huang, Shuai; Wang, Qiyi; Liu, Yongguo; Sun, Baoguo; Tian, Hongyu [Synthetic Communications, 2020, vol. 50, # 15, p. 2319 - 2330]

53
[ 112-45-8 ]
[ 4648-54-8 ]
dec-9-en-1-ylcarbamoyl azide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With tert-Butyl peroxybenzoate; copper(II) bis(oxalato)cuprate(II) monohydrate In acetonitrile at 70℃; for 16h; Inert atmosphere; Schlenk technique;	Copper-Catalyzed Azidation of Aldehydes; Phenylcarbamoyl Azide(3a); Typical Procedure (Table 1 and Scheme 2) Benzaldehyde (1a; 53 mg, 0.5 mmol, 1 equiv), TMSN3 (2; 173 mg, 1.5mmol, 3 equiv), MeCN (2 mL), TBPB (145 mg, 0.75 mmol, 1.5 equiv), and (CuC2O4)2·H2O (4 mg, 2.5 mol%) were placed in a Schlenk tube with a stirring bar under a N2 atmosphere. The reaction mixture was heated at 70 °C for 16 h, and then cooled to r.t. The reaction was quenched with EtOAc, and then washed with H2O (3 × 15 mL). The combined organic phases were dried (MgSO4). The solvent was removed by evaporation under vacuum and the residue was chromatographed on silica gel (PE/EtOAc 20:1 → 5:1) to yield 3a as a white solid; yield: 69.8 mg (86%); mp 106-107 °C (Lit.15 mp 106-107 °C).1H NMR (600 MHz, CDCl3): = 7.46 (d, J = 7.9 Hz, 2 H), 7.38 (br, 1 H),7.32 (t, J = 7.9 Hz, 2 H), 7.13 (t, J = 7.3 Hz, 1 H).13C NMR (150 MHz, CDCl3): = 154.37, 137.06, 129.18, 124.76,119.58.

Reference： [1]Bao, Hongli; Ge, Liang; Li, Yajun; Liao, Saihu; Wei, Rongbiao [Synthesis, 2019, vol. 51, # 24, p. 4645 - 4649]

54
[ 112-45-8 ]
[ 5978-75-6 ]
(9H-fluoren-9-yl)undec-10-enylidene-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; cyclohexane at 0 - 20℃; for 2h; Schlenk technique; Inert atmosphere; Molecular sieve;

Reference： [1]Wan, Li-Qiang; Cao, Jin-Ge; Niu, Dawen; Zhang, Xia [Organic Letters, 2021, vol. 23, # 10, p. 3818 - 3822]

55
[ 112-45-8 ]
[ 5978-75-6 ]
N-(1-(1,3-dioxolan-2-yl)dodec-11-en-2-yl)-9H-fluoren-9-imine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: cyclohexane; dichloromethane / 2 h / 0 - 20 °C / Schlenk technique; Inert atmosphere; Molecular sieve 2.1: cobalt(II) bromide / diethyl ether / 0.17 h / 25 °C / Sealed tube 2.2: 2.17 h / -20 - 25 °C / Sealed tube

Reference： [1]Wan, Li-Qiang; Cao, Jin-Ge; Niu, Dawen; Zhang, Xia [Organic Letters, 2021, vol. 23, # 10, p. 3818 - 3822]

56
[ 112-45-8 ]
[ 53179-04-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With ferric(III) bromide; trimethylsilylazide In acetonitrile at 80℃; for 4h;

Reference： [1]Chatterjee, Basujit; Jena, Soumyashree; Chugh, Vishal; Weyhermüller, Thomas; Werlé, Christophe [ACS Catalysis, 2021, vol. 11, # 12, p. 7176 - 7185]

57
[ 112-45-8 ]
[ 5332-51-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With trimethylsilylazide; tetrabutylammomium bromide; iron(II) bromide In neat (no solvent) at 60℃; for 4h; Irradiation;

Reference： [1]Chatterjee, Basujit; Jena, Soumyashree; Chugh, Vishal; Weyhermüller, Thomas; Werlé, Christophe [ACS Catalysis, 2021, vol. 11, # 12, p. 7176 - 7185]

58
[ 67-56-1 ]
[ 112-45-8 ]
[ 149-73-5 ]
[ 65405-66-5 ]

Yield	Reaction Conditions	Operation in experiment
97.6%	With povidone-iodine at 30℃; for 3h; Green chemistry;	5. General procedures General procedure: To a 25 mL round-bottomed flask was charged with starting material (1.0 mmol), PVP-I (76 mg, 0.03 mmol of effective iodine), Trimethyl orthoformate (1.0 mmol, 0.24 mL) and MeOH (2.0 mL). The mixture was stirred for 3 h at 30 °C. After that, the solvent was evaporated. The resulting mixture was suspended in water (20 mL)and extracted with EA (10 mL x 3). The combined organic layer was washed with brine (20 mL) and dried over anhydrous Na2SO4. After filtration and concentrated under reduced pressure, most of the products were pure enough. The residue could be further purified by flash column chromatography to give the fine products.

Reference： [1]Cao, Fu-Rong; Lu, Guangying; Ren, Jiangmeng; Wang, Di; Zeng, Bu-Bing [Tetrahedron, 2021, vol. 92]

59
[ 64-17-5 ]
[ 112-45-8 ]
[ 122-51-0 ]
[ 54986-31-1 ]

Yield	Reaction Conditions	Operation in experiment
96.1%	With povidone-iodine at 30℃; for 3h; Green chemistry;	5. General procedures General procedure: To a 25 mL round-bottomed flask was charged with starting material (1.0 mmol), PVP-I (76 mg, 0.03 mmol of effective iodine), Trimethyl orthoformate (1.0 mmol, 0.24 mL) and MeOH (2.0 mL). The mixture was stirred for 3 h at 30 °C. After that, the solvent was evaporated. The resulting mixture was suspended in water (20 mL)and extracted with EA (10 mL x 3). The combined organic layer was washed with brine (20 mL) and dried over anhydrous Na2SO4. After filtration and concentrated under reduced pressure, most of the products were pure enough. The residue could be further purified by flash column chromatography to give the fine products.

Reference： [1]Cao, Fu-Rong; Lu, Guangying; Ren, Jiangmeng; Wang, Di; Zeng, Bu-Bing [Tetrahedron, 2021, vol. 92]

60
[ 112-45-8 ]
[ 3066-71-5 ]
C₁₈H₃₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With C₄₂H₅₃N₃O₄Ru In tetrahydrofuran at 25℃; for 48h; Inert atmosphere; Glovebox; Sealed tube; stereoselective reaction;

Reference： [1]Gan, Quan; Grubbs, Robert H.; Ko, Jeong Hoon; Samkian, Adrian E.; Xu, Yan [Angewandte Chemie - International Edition, 2022, vol. 61, # 4][Angew. Chem., 2022, vol. 134, # 4]

61
[ 64-18-6 ]
[ 112-45-8 ]
C₁₂H₂₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With acetic anhydride; C₂₇H₂₅O₃P; lithium chloride; palladium (II) chloride In 1,4-dioxane at 70℃; for 24h; Inert atmosphere;	17 Example 17. Carboxylic acid (see structural formula II-q): PdCl2 (0.0044g, 0.025mmol), LiCl (0.0212g, 0.50mmol) and ligand L (0.0214g, 0.050mmol) were added to a 2mL pressure-resistant tube, and 1.0mL of the first organic solvent 1,4-dioxygen was added Hexacyclic and 10-undecene aldehyde I-q (0.0841 g, 0.50 mmol) and acetic anhydride (0.0511 g, 0.50 mmol) and formic acid (0.046 g, 1.0 mmol) were charged with Ar, and the reaction was placed at 70 °C for 24 h. It was cooled to room temperature and purified by column separation. The specific conditions are: packing the column with petroleum ether, and the eluent is petroleum ether/ethyl acetate to obtain a colorless liquid II-q (0.0606 g, 57% yield), and the ratio of branched chain to straight chain is 6.5:1.

Reference： [1]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN114315563, 2022, A Location in patent: Paragraph 0102-0106

62
[ 112-45-8 ]
[ 423-39-2 ]
C₁₅H₂₀F₉IO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With Au single-atom sites decorated hexagonal cadmiumsulfide nanocatalyst In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation; Inert atmosphere;	2.4. Blue-LED-induced ATRA reactions The LED-induced ATRA reaction model is shown as Scheme 2.Briefly, the alkene 1 (0.3 mmol) and CatCdS-Au (4.2 mg) were addedto a glass tube equipped with a magnetic stir bar. The tube wasevacuated and refilled with argon for three times through a sealedseptum, and 1.5 mL anhydrous DMF was added and followed by afurther evacuated and refilled with argon for three times. Then, RfI(0.45 mmol) was added dropwise to the solution, and the tube wassealed and illuminated at room temperature for 12 h under a 32Wblue-LED annular lamp tape. The reaction mixture was quenchedby H2O and extracted for three times with ethyl acetate. Theorganic phase was collected and washed with water and brine,then it was dried over anhydrous Na2SO4 followed by a filtrationand concentrated by a rotary evaporator. The crude product waspurified by flash column chromatography on silica gel to obtainthe resultant product 2.

Reference： [1]Hao, Xiao-Li; Chu, Xiao-Shan; Luo, Ke-Ling; Li, Wei [Journal of Catalysis, 2022, vol. 411, p. 226 - 234]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	112-45-8	MDL No. :	MFCD00007032
Formula :	C₁₁H₂₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OFHHDSQXFXLTKC-UHFFFAOYSA-N
M.W :	168.28	Pubchem ID :	8187
Synonyms :	Undecylenic Aldehyde

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P272-P273-P280-P302+P352	UN#:	N/A
Hazard Statements:	H315-H412	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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 112-45-8 ] {[proInfo.proName]}

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[ 112-45-8 ] Synthesis Path-Downstream 1~62

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[ 112-45-8 ]

Alkenes

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