1,4-二噁螺[4.5]癸烷-8-甲醛合成路线 （共 19 条）
反应条件
1.1: sodium cyanide / ethanol / 2 h 1.2: 75 percent / NH3 / ethanol / 16 h / 90 - 110 °C 2.1: 94 percent / HCl / 1 h / 20 °C View Scheme
参考文献
Kitbunnadaj, Ruengwit; Hoffmann, Marcel; Fratantoni, Silvina A.; Bongers, Gerold; Bakker, Remko A.; Wieland, Kerstin; El Jilali, Ahmed; De Esch, Iwan J. P.; Menge, Wiro M. P. B.; Timmerman, Henk; Leurs, Rob
Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 23 p. 6309 - 6323
反应条件
hydrogenchloride in tetrahydrofuran T=50°C; 3 h;
参考文献
Gangjee; Zaveri; Queener; Kisliuk
Journal of Heterocyclic Chemistry, 1995 , vol. 32, # 1 p. 243 - 247
反应条件
1: 1) NaOMe / 1) DMSO, r.t., 15 min, 2) r.t., 1 day 2: 68 percent / H2 / 5percent Pd-C / methanol / 2280 Torr 3: 84 percent / CF3COOH / tetrahydrofuran; H2O / 2 h / 60 - 65 °C View Scheme
参考文献
Rosowsky, Andre; Forsch, Ronald A.; Moran, Richard G.
Journal of Medicinal Chemistry, 1989 , vol. 32, # 3 p. 709 - 715
反应条件
diisobutylaluminium hydride in toluene
T=-70 - -65°C; 0.5 - 1 h;
参考文献
Gruenenthal GMBH
Patent: US2009/48323 A1, 2009 ;
Location in patent: Page/Page column 14; 16 ;
反应条件
oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane
T=-60 - 20°C; Swern oxidation; 2 h;
参考文献
Kitbunnadaj, Ruengwit; Hoffmann, Marcel; Fratantoni, Silvina A.; Bongers, Gerold; Bakker, Remko A.; Wieland, Kerstin; El Jilali, Ahmed; De Esch, Iwan J. P.; Menge, Wiro M. P. B.; Timmerman, Henk; Leurs, Rob
Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 23 p. 6309 - 6323
反应条件
hydrogen; palladium on activated charcoal in ethanol
P=1551.4 - 2068.6 Torr; 10 h; Title compound not separated from byproducts;
参考文献
Berkowitz, W. F.; Amarasekara, A. S.; Perumattam, J. J.
Journal of Organic Chemistry, 1987 , vol. 52, # 6 p. 1119 - 1124
反应条件
triethylamine in dichloromethane; water
参考文献
The Wellcome Foundation Ltd.; The Regents of the University of California
Patent: US4985411 A1, 1991 ;
反应条件
1: 83 percent / BF3*Et2O
2: H2 / 10percent Pd/C / ethanol / 10 h / 1551.4 - 2068.6 Torr
View Scheme
参考文献
Berkowitz, W. F.; Amarasekara, A. S.; Perumattam, J. J.
Journal of Organic Chemistry, 1987 , vol. 52, # 6 p. 1119 - 1124
反应条件
1: 95 percent / LiAlH4 / diethyl ether / 3 h / 20 °C
2: 97 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 2 h / -60 - 20 °C
View Scheme
参考文献
Kitbunnadaj, Ruengwit; Hoffmann, Marcel; Fratantoni, Silvina A.; Bongers, Gerold; Bakker, Remko A.; Wieland, Kerstin; El Jilali, Ahmed; De Esch, Iwan J. P.; Menge, Wiro M. P. B.; Timmerman, Henk; Leurs, Rob
Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 23 p. 6309 - 6323
反应条件
1: 90 percent / p-toluenesulfonic acid monohydrate / toluene / 18 h / Heating
2: 95 percent / LiAlH4 / diethyl ether / 3 h / 20 °C
3: 97 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 2 h / -60 - 20 °C
View Scheme
参考文献
Kitbunnadaj, Ruengwit; Hoffmann, Marcel; Fratantoni, Silvina A.; Bongers, Gerold; Bakker, Remko A.; Wieland, Kerstin; El Jilali, Ahmed; De Esch, Iwan J. P.; Menge, Wiro M. P. B.; Timmerman, Henk; Leurs, Rob
Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 23 p. 6309 - 6323
