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乙二醇
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63148-62-9
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碳酸氢钠
471-34-1
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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
192133-57-6
合成路线
（共 5 条）
192133-57-6
→
反应条件
6879-74-9
(+)-喜巴辛
反应条件
1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 2: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 3: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 4: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme
参考文献
Hart, David J.; Li, Jing; Wu, Wen-Lian; Kozikowski, Alan P.
Journal of Organic Chemistry, 1997 , vol. 62, # 15 p. 5023 - 5033
129272-02-2
→
反应条件
192133-57-6
反应条件
<b>Multi-step reaction with 17 steps<br /> </b>1.1: triethylamine / CH<sub>2</sub>Cl<sub>2</sub> / 1.5 h / 0 °C<br />2.1: 84 percent / DBU / 2 h / 80 °C<br />3.1: 47 percent / H<sub>2</sub> / 10 percent Pd/C / ethanol / 4 h / 0 - 10 °C / 760 Torr<br />4.1: lithium perchlorate / diethyl ether / 168 h / 20 °C<br />5.1: 96 percent / H<sub>2</sub> / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr<br />6.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C<br />7.1: 83 percent / DBU / toluene / 5 h / 100 °C<br />8.1: 96 percent / H<sub>2</sub> / PtO<sub>2</sub> / ethanol / 16 h / 20 °C / 760 Torr<br />9.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C<br />10.1: 1.50 g / BF<sub>3</sub>*Et<sub>2</sub>O / CH<sub>2</sub>Cl<sub>2</sub> / 12 h / -60 °C<br />11.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH<sub>2</sub>Cl<sub>2</sub> / 1.5 h / 20 °C<br />12.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C<br />12.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C<br />13.1: BH<sub>3</sub>*THF / tetrahydrofuran / 3 h / -78 °C<br />13.2: 73 percent / aq. NaOH; H<sub>2</sub>O<sub>2</sub> / 0.5 h / 0 °C<br />14.1: triethylamine; 4-(dimethylamino)pyridine / CH<sub>2</sub>Cl<sub>2</sub> / 3 h / 0 °C<br />15.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C<br />16.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH<sub>2</sub>Cl<sub>2</sub> / 2 h / 20 °C<br />17.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C<br />17.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C<br /> <br />
参考文献
Takadoi, Masanori; Katoh, Tadashi; Ishiwata, Akihiro; Terashima, Shiro Tetrahedron, 2002 , vol. 58, # 50 p. 9903 - 9923
229010-18-8
→
反应条件
192133-57-6
反应条件
<b>Multi-step reaction with 12 steps<br /> </b>1.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C<br />2.1: 83 percent / DBU / toluene / 5 h / 100 °C<br />3.1: 96 percent / H<sub>2</sub> / PtO<sub>2</sub> / ethanol / 16 h / 20 °C / 760 Torr<br />4.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C<br />5.1: 1.50 g / BF<sub>3</sub>*Et<sub>2</sub>O / CH<sub>2</sub>Cl<sub>2</sub> / 12 h / -60 °C<br />6.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH<sub>2</sub>Cl<sub>2</sub> / 1.5 h / 20 °C<br />7.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C<br />7.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C<br />8.1: BH<sub>3</sub>*THF / tetrahydrofuran / 3 h / -78 °C<br />8.2: 73 percent / aq. NaOH; H<sub>2</sub>O<sub>2</sub> / 0.5 h / 0 °C<br />9.1: triethylamine; 4-(dimethylamino)pyridine / CH<sub>2</sub>Cl<sub>2</sub> / 3 h / 0 °C<br />10.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C<br />11.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH<sub>2</sub>Cl<sub>2</sub> / 2 h / 20 °C<br />12.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C<br />12.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C<br /> <br />
参考文献
Takadoi, Masanori; Katoh, Tadashi; Ishiwata, Akihiro; Terashima, Shiro Tetrahedron, 2002 , vol. 58, # 50 p. 9903 - 9923
503443-47-8
→
反应条件
192133-57-6
反应条件
<b>Multi-step reaction with 15 steps<br /> </b>1.1: 47 percent / H<sub>2</sub> / 10 percent Pd/C / ethanol / 4 h / 0 - 10 °C / 760 Torr<br />2.1: lithium perchlorate / diethyl ether / 168 h / 20 °C<br />3.1: 96 percent / H<sub>2</sub> / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr<br />4.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C<br />5.1: 83 percent / DBU / toluene / 5 h / 100 °C<br />6.1: 96 percent / H<sub>2</sub> / PtO<sub>2</sub> / ethanol / 16 h / 20 °C / 760 Torr<br />7.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C<br />8.1: 1.50 g / BF<sub>3</sub>*Et<sub>2</sub>O / CH<sub>2</sub>Cl<sub>2</sub> / 12 h / -60 °C<br />9.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH<sub>2</sub>Cl<sub>2</sub> / 1.5 h / 20 °C<br />10.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C<br />10.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C<br />11.1: BH<sub>3</sub>*THF / tetrahydrofuran / 3 h / -78 °C<br />11.2: 73 percent / aq. NaOH; H<sub>2</sub>O<sub>2</sub> / 0.5 h / 0 °C<br />12.1: triethylamine; 4-(dimethylamino)pyridine / CH<sub>2</sub>Cl<sub>2</sub> / 3 h / 0 °C<br />13.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C<br />14.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH<sub>2</sub>Cl<sub>2</sub> / 2 h / 20 °C<br />15.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C<br />15.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C<br /> <br />
参考文献
Takadoi, Masanori; Katoh, Tadashi; Ishiwata, Akihiro; Terashima, Shiro Tetrahedron, 2002 , vol. 58, # 50 p. 9903 - 9923
503443-60-5
→
反应条件
192133-57-6
反应条件
<b>Multi-step reaction with 16 steps<br /> </b>1.1: 84 percent / DBU / 2 h / 80 °C<br />2.1: 47 percent / H<sub>2</sub> / 10 percent Pd/C / ethanol / 4 h / 0 - 10 °C / 760 Torr<br />3.1: lithium perchlorate / diethyl ether / 168 h / 20 °C<br />4.1: 96 percent / H<sub>2</sub> / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr<br />5.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C<br />6.1: 83 percent / DBU / toluene / 5 h / 100 °C<br />7.1: 96 percent / H<sub>2</sub> / PtO<sub>2</sub> / ethanol / 16 h / 20 °C / 760 Torr<br />8.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C<br />9.1: 1.50 g / BF<sub>3</sub>*Et<sub>2</sub>O / CH<sub>2</sub>Cl<sub>2</sub> / 12 h / -60 °C<br />10.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH<sub>2</sub>Cl<sub>2</sub> / 1.5 h / 20 °C<br />11.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C<br />11.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C<br />12.1: BH<sub>3</sub>*THF / tetrahydrofuran / 3 h / -78 °C<br />12.2: 73 percent / aq. NaOH; H<sub>2</sub>O<sub>2</sub> / 0.5 h / 0 °C<br />13.1: triethylamine; 4-(dimethylamino)pyridine / CH<sub>2</sub>Cl<sub>2</sub> / 3 h / 0 °C<br />14.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C<br />15.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH<sub>2</sub>Cl<sub>2</sub> / 2 h / 20 °C<br />16.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C<br />16.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C<br /> <br />
参考文献
Takadoi, Masanori; Katoh, Tadashi; Ishiwata, Akihiro; Terashima, Shiro Tetrahedron, 2002 , vol. 58, # 50 p. 9903 - 9923
