1,4-环己二酮单乙二醇缩酮合成路线 （共 270 条）
反应条件
1: acetylene With n-propyl-magnesium bromide in tetrahydrofuran
T=0°C; 1.5 h;
2: 1,4-cyclohexanedione monoacetal in tetrahydrofuran
T=20°C; 3.5 h; Further stages.;
参考文献
Pouwer, Rebecca H.; Schill, Heiko; Williams, Craig M.; Bernhardt, Paul V.
European Journal of Organic Chemistry, 2007 , # 28 p. 4699 - 4705
反应条件
in tetrahydrofuran
T=0 - 20°C; 2 h; Inert atmosphere;
参考文献
Hiller, Christine; Kling, Ralf C.; Heinemann, Frank W.; Meyer, Karsten; Huebner, Harald; Gmeiner, Peter
Journal of Medicinal Chemistry, 2013 , vol. 56, # 12 p. 5130 - 5141
反应条件
1: trimethylsilylacetylene With lithium hexamethyldisilazane in tetrahydrofuran
T=-10°C; Metallation; 0.5 h;
2: 1,4-cyclohexanedione monoacetal in tetrahydrofuran
T=-10°C; Addition; 3 h; Further stages.;
参考文献
Allan, Graham; Carnell, Andrew J.; Hernandez, Maria Luisa Escudero; Pettman, Alan
Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 20 p. 3382 - 3388
反应条件
1: 1.) LDA / 1.) THF
2: Heating
3: 95 percent / n-BuLi / tetrahydrofuran / 0.7 h / -45 up to -35 deg C
View Scheme
参考文献
Toray Industries, Inc.
Patent: EP2341047 A1, 2011 ;
反应条件
in tetrahydrofuran
T=0 - 20°C; Inert atmosphereSchlenk technique;
参考文献
Semba, Kazuhiko; Fujihara, Tetsuaki; Terao, Jun; Tsuji, Yasushi
Angewandte Chemie - International Edition, 2013 , vol. 52, # 47 p. 12400 - 12403
Angew. Chem., 2013 , vol. 125, # 47 p. 12626 - 12629,4
反应条件
1: 1,4-cyclohexanedione monoacetal With lithium hexamethyldisilazane in tetrahydrofuran
T=-78°C; 0.566667 h;
2: methyl iodide in tetrahydrofuran
T=-78 - 20°C; 2.33333 h;
参考文献
MEMORIAL SLOAN-KETTERING CANCER CENTER
Patent: WO2006/19673 A2, 2006 ;
Location in patent: Page/Page column 34; 60 ;
反应条件
1: 1,3-thiazole With n-butyllithium in tetrahydrofuran; hexanes
T=-78°C; 1 h;
2: 1,4-cyclohexanedione monoacetal in tetrahydrofuran; hexanes
T=-78°C; 3 h;
3: With water in tetrahydrofuran; hexanes
T=-78 - 20°C;
参考文献
PFIZER LIMITED; BURGESS, Gary
Patent: WO2012/114223 A1, 2012 ;
Location in patent: Page/Page column 46 ;
WO 2012/114223 A1
反应条件
1: 1,3-thiazole With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 1 h;
2: 1,4-cyclohexanedione monoacetal in tetrahydrofuran; hexane
T=-78°C; 3 h;
3: With water in tetrahydrofuran; hexane
T=-78 - 20°C;
参考文献
Xue, Chu-Biao; Metcalf, Brian W.; Han, Amy Qi; Robinson, Darius J.; Zheng, Changsheng; Wang, Anlai; Zhang, Yingxin
Patent: US2005/192302 A1, 2005 ;
Location in patent: Page/Page column 26 ;
US 20050192302 A1
反应条件
1: 2-bromo-1,3-thiazole With n-butyllithium in diethyl ether; hexane
T=-78 - -60°C; 0.25 - 0.916667 h;
2: 1,4-cyclohexanedione monoacetal in diethyl ether; hexane
T=-78 - 20°C; 3 h; Product distribution / selectivity;
参考文献
ABBOTT LABORATORIES
Patent: US2009/124671 A1, 2009 ;
Location in patent: Page/Page column 21; 23 ;
反应条件
1: 62 percent / NH3 (gas) / ethane-1,2-diol / 1 h / 150 - 160 °C
2: 87 percent / 30percent aq. H2O2 / acetic acid / 5 h / 80 °C
3: 78 percent / 1 h / 90 °C
4: 69 percent / Br2, MeOH / 0.33 h / Heating
5: 92 percent / 10percent aq. HCl / 1 h / 40 °C
6: 54 percent / 20percent aq. KOH / 1 h / Heating
View Scheme
参考文献
Del Giudice, Maria Rosaria; Borioni, Anna; Mustazza, Carlo; Gatta, Franco
Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 6 p. 1661 - 1667
