7-溴-3,4-二氢萘-1(2H)-酮合成路线 （共 31 条）
反应条件
1: 87 percent / NaBH4 / ethanol; tetrahydrofuran
2: 95 percent / p-toluenesulfonic acid * H2O / benzene / Heating
3: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating
4: 99 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr
View Scheme
参考文献
Adamczyk, Maciej; Watt, David S.; Netzel, Daniel A.
Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4226 - 4237
反应条件
1: 87 percent / NaBH4 / ethanol; tetrahydrofuran
2: 95 percent / p-toluenesulfonic acid * H2O / benzene / Heating
3: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating
4: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr
View Scheme
参考文献
Adamczyk, Maciej; Watt, David S.; Netzel, Daniel A.
Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4226 - 4237
反应条件
sodium tetrahydroborate in methanol; dichloromethane
T=20 - 23°C; 1 h;
参考文献
Saito, Masahiko; Kayama, Yasutaka; Watanabe, Tamaki; Fukushima, Hisashi; Hara, Takeshi; et al.
Journal of Medicinal Chemistry, 1980 , vol. 23, # 12 p. 1364 - 1372
反应条件
(i) Al(OiPr)3, (ii) KHSO4; Multistep reaction;
参考文献
Chini, Marco; Crotti, Paolo; Minutolo, Filippo; Martinelli, Adriano; Micali, Eugenio
Gazzetta Chimica Italiana, 1994 , vol. 124, # 1 p. 27 - 34
反应条件
1: NaBH4 / ethanol / 2 h / Ambient temperature
2: 1.3 g / p-toluenesulfonc acid / benzene / 0.67 h / Heating
3: N-bromoacetamide / tetrahydrofuran; H2O / 1 h / Ambient temperature
4: t-BuOK / benzene / 2 h / Ambient temperature
View Scheme
参考文献
Saito, Masahiko; Kayama, Yasutaka; Watanabe, Tamaki; Fukushima, Hisashi; Hara, Takeshi; et al.
Journal of Medicinal Chemistry, 1980 , vol. 23, # 12 p. 1364 - 1372
反应条件
1: With hydroxylamine hydrochloride; sodium methylate in methanol
T=60°C; 20 h;
2: With PPA
T=130°C; 0.2 h;
参考文献
XENON PHARMACEUTICALS INC.
Patent: WO2008/46046 A1, 2008 ;
Location in patent: Page/Page column 75 ;
WO 2008/046046 A1
反应条件
1: With tetra-n-butylammonium tribromide in methanol; dichloromethane
T=20°C; 16 h;
2: With lithium carbonate; lithium bromide in N,N-dimethyl-formamide
T=140°C; 1.5 h;
参考文献
Molino, Bruce F.; Liu, Shuang; Guzzo, Peter R.; Beck, James P.
Patent: US2006/52378 A1, 2006 ;
Location in patent: Page/Page column 113 ;
US 20060052378 A1
反应条件
1.1: p-toluenesulfonic acid monohydrate; trimethyl orthoformate / methanol; benzene / 40 h / Heating
1.2: 75 percent / p-toluenesulfonic acid monohydrate / benzene / 4 h / Heating
2.1: n-BuLi / tetrahydrofuran; pentane / 0.67 h / -78 °C
2.2: 78 percent / tetrahydrofuran; pentane / 1.25 h / cooling
3.1: 85 percent / boron tribromide / CH2Cl2 / -35 - 0 °C
View Scheme
参考文献
Heller, Douglas P.; Goldberg, Daniel R.; Wu, Hongqiao; Wulff, William D.
Canadian Journal of Chemistry, 2006 , vol. 84, # 10 p. 1487 - 1503
反应条件
1: 87 percent / NaBH4 / ethanol; tetrahydrofuran
2: 95 percent / p-toluenesulfonic acid * H2O / benzene / Heating
3: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating
4: 98 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr
View Scheme
参考文献
Adamczyk, Maciej; Watt, David S.; Netzel, Daniel A.
Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4226 - 4237
反应条件
1.1: trifluoroacetic acid; triethylsilane / 4 h / 20 - 50 °C
2.1: n-butyllithium / hexane; tetrahydrofuran / 1.5 h / Cooling with acetone-dry ice; Inert atmosphere
2.2: 3.83 h
2.3: pH 8 / Cooling
View Scheme
参考文献
Nissan Chemical Industries, Ltd.
Patent: US2012/209005 A1, 2012 ;
