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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
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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
467-16-3
合成路线
(共 30 条)
467-16-3
→
反应条件
57-24-9
马钱子碱
反应条件
potassium hydroxide in ethanol T=85°C; 6 h;
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
64-17-5
乙醇
+
467-16-3
→
反应条件
57-24-9
马钱子碱
反应条件
暂无反应条件数据
参考文献
Prelog et al.
Helvetica Chimica Acta, 1948 , vol. 31, p. 2244
Full Text Show Details
Woodward et al.
Tetrahedron, 1963 , vol. 19, p. 247,256, 270
Journal of the American Chemical Society, 1954 , vol. 76, p. 4749
467222-58-8
→
反应条件
467-16-3
反应条件
hydrogenchloride in tetrahydrofuran T=20°C; 3 h;
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
350677-99-5
→
反应条件
467-16-3
反应条件
1.1: LiAlH4 / tetrahydrofuran / 1.5 h / 20 °C 2.1: 3.22 g / Et3N / dimethylformamide / 1 h / 20 °C 3.1: 77 percent / MnO2; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C 4.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C 4.2: aq. NaOH; H2O2 / tetrahydrofuran / 4 h / 20 °C 5.1: 87 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C 6.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C 7.1: 100 percent / PPh3; HCO2H; iPr2NEt / Pd(OAc)2 / dimethylformamide / 1 h / 60 °C 8.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 0.25 h / -78 °C 9.1: 18.0 mg / K2CO3 / tetrahydrofuran / 0.5 h / 0 °C 10.1: 46 percent / Pd(OAc)2; PPh3; i-Pr2NEt / dimethylsulfoxide / 1.5 h / 80 °C 11.1: 81 percent / NaOiPr / propan-2-ol / 1 h / 20 °C 12.1: CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 13.1: 7.1 mg / Li2CO3 / dimethylformamide / 14 h / 40 °C 14.1: 48 percent / PPh3; K2CO3; Bu4NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C 15.1: 47 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0 °C 16.1: 96 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C View Scheme
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
350677-98-4
→
反应条件
467-16-3
反应条件
1.1: 73 percent / Pd(OAc)2; Me2PPh; Ag2CO3 / dimethylsulfoxide / 17 h / 90 °C 2.1: LiAlH4 / tetrahydrofuran / 1.5 h / 20 °C 3.1: 3.22 g / Et3N / dimethylformamide / 1 h / 20 °C 4.1: 77 percent / MnO2; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C 5.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C 5.2: aq. NaOH; H2O2 / tetrahydrofuran / 4 h / 20 °C 6.1: 87 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C 7.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C 8.1: 100 percent / PPh3; HCO2H; iPr2NEt / Pd(OAc)2 / dimethylformamide / 1 h / 60 °C 9.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 0.25 h / -78 °C 10.1: 18.0 mg / K2CO3 / tetrahydrofuran / 0.5 h / 0 °C 11.1: 46 percent / Pd(OAc)2; PPh3; i-Pr2NEt / dimethylsulfoxide / 1.5 h / 80 °C 12.1: 81 percent / NaOiPr / propan-2-ol / 1 h / 20 °C 13.1: CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 14.1: 7.1 mg / Li2CO3 / dimethylformamide / 14 h / 40 °C 15.1: 48 percent / PPh3; K2CO3; Bu4NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C 16.1: 47 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0 °C 17.1: 96 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C View Scheme
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
350678-00-1
→
反应条件
467-16-3
反应条件
1.1: 77 percent / MnO2; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C 2.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C 2.2: aq. NaOH; H2O2 / tetrahydrofuran / 4 h / 20 °C 3.1: 87 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C 4.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C 5.1: 100 percent / PPh3; HCO2H; iPr2NEt / Pd(OAc)2 / dimethylformamide / 1 h / 60 °C 6.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 0.25 h / -78 °C 7.1: 18.0 mg / K2CO3 / tetrahydrofuran / 0.5 h / 0 °C 8.1: 46 percent / Pd(OAc)2; PPh3; i-Pr2NEt / dimethylsulfoxide / 1.5 h / 80 °C 9.1: 81 percent / NaOiPr / propan-2-ol / 1 h / 20 °C 10.1: CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 11.1: 7.1 mg / Li2CO3 / dimethylformamide / 14 h / 40 °C 12.1: 48 percent / PPh3; K2CO3; Bu4NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C 13.1: 47 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0 °C 14.1: 96 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C View Scheme
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
350677-95-1
→
反应条件
467-16-3
反应条件
1.1: 100 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C 2.1: 90 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 - 20 °C 3.1: 95 percent / dimethylsulfoxide / 1 h / 20 °C 4.1: 73 percent / Pd(OAc)2; Me2PPh; Ag2CO3 / dimethylsulfoxide / 17 h / 90 °C 5.1: LiAlH4 / tetrahydrofuran / 1.5 h / 20 °C 6.1: 3.22 g / Et3N / dimethylformamide / 1 h / 20 °C 7.1: 77 percent / MnO2; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C 8.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C 8.2: aq. NaOH; H2O2 / tetrahydrofuran / 4 h / 20 °C 9.1: 87 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C 10.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C 11.1: 100 percent / PPh3; HCO2H; iPr2NEt / Pd(OAc)2 / dimethylformamide / 1 h / 60 °C 12.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 0.25 h / -78 °C 13.1: 18.0 mg / K2CO3 / tetrahydrofuran / 0.5 h / 0 °C 14.1: 46 percent / Pd(OAc)2; PPh3; i-Pr2NEt / dimethylsulfoxide / 1.5 h / 80 °C 15.1: 81 percent / NaOiPr / propan-2-ol / 1 h / 20 °C 16.1: CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 17.1: 7.1 mg / Li2CO3 / dimethylformamide / 14 h / 40 °C 18.1: 48 percent / PPh3; K2CO3; Bu4NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C 19.1: 47 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0 °C 20.1: 96 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C View Scheme
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
350678-16-9
→
反应条件
467-16-3
反应条件
1.1: 95 percent / dimethylsulfoxide / 1 h / 20 °C 2.1: 73 percent / Pd(OAc)2; Me2PPh; Ag2CO3 / dimethylsulfoxide / 17 h / 90 °C 3.1: LiAlH4 / tetrahydrofuran / 1.5 h / 20 °C 4.1: 3.22 g / Et3N / dimethylformamide / 1 h / 20 °C 5.1: 77 percent / MnO2; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C 6.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C 6.2: aq. NaOH; H2O2 / tetrahydrofuran / 4 h / 20 °C 7.1: 87 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C 8.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C 9.1: 100 percent / PPh3; HCO2H; iPr2NEt / Pd(OAc)2 / dimethylformamide / 1 h / 60 °C 10.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 0.25 h / -78 °C 11.1: 18.0 mg / K2CO3 / tetrahydrofuran / 0.5 h / 0 °C 12.1: 46 percent / Pd(OAc)2; PPh3; i-Pr2NEt / dimethylsulfoxide / 1.5 h / 80 °C 13.1: 81 percent / NaOiPr / propan-2-ol / 1 h / 20 °C 14.1: CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 15.1: 7.1 mg / Li2CO3 / dimethylformamide / 14 h / 40 °C 16.1: 48 percent / PPh3; K2CO3; Bu4NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C 17.1: 47 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0 °C 18.1: 96 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C View Scheme
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
350678-15-8
→
反应条件
467-16-3
反应条件
1.1: 90 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 - 20 °C 2.1: 95 percent / dimethylsulfoxide / 1 h / 20 °C 3.1: 73 percent / Pd(OAc)2; Me2PPh; Ag2CO3 / dimethylsulfoxide / 17 h / 90 °C 4.1: LiAlH4 / tetrahydrofuran / 1.5 h / 20 °C 5.1: 3.22 g / Et3N / dimethylformamide / 1 h / 20 °C 6.1: 77 percent / MnO2; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C 7.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C 7.2: aq. NaOH; H2O2 / tetrahydrofuran / 4 h / 20 °C 8.1: 87 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C 9.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C 10.1: 100 percent / PPh3; HCO2H; iPr2NEt / Pd(OAc)2 / dimethylformamide / 1 h / 60 °C 11.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 0.25 h / -78 °C 12.1: 18.0 mg / K2CO3 / tetrahydrofuran / 0.5 h / 0 °C 13.1: 46 percent / Pd(OAc)2; PPh3; i-Pr2NEt / dimethylsulfoxide / 1.5 h / 80 °C 14.1: 81 percent / NaOiPr / propan-2-ol / 1 h / 20 °C 15.1: CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 16.1: 7.1 mg / Li2CO3 / dimethylformamide / 14 h / 40 °C 17.1: 48 percent / PPh3; K2CO3; Bu4NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C 18.1: 47 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0 °C 19.1: 96 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C View Scheme
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
1024-38-0
→
反应条件
467-16-3
反应条件
1.1: Pd2dba3*CHCl3; (S)-BINAPO / dimethylformamide / 21 h / 0 °C 2.1: 100 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C 3.1: 90 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 - 20 °C 4.1: 95 percent / dimethylsulfoxide / 1 h / 20 °C 5.1: 73 percent / Pd(OAc)2; Me2PPh; Ag2CO3 / dimethylsulfoxide / 17 h / 90 °C 6.1: LiAlH4 / tetrahydrofuran / 1.5 h / 20 °C 7.1: 3.22 g / Et3N / dimethylformamide / 1 h / 20 °C 8.1: 77 percent / MnO2; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C 9.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C 9.2: aq. NaOH; H2O2 / tetrahydrofuran / 4 h / 20 °C 10.1: 87 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C 11.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C 12.1: 100 percent / PPh3; HCO2H; iPr2NEt / Pd(OAc)2 / dimethylformamide / 1 h / 60 °C 13.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 0.25 h / -78 °C 14.1: 18.0 mg / K2CO3 / tetrahydrofuran / 0.5 h / 0 °C 15.1: 46 percent / Pd(OAc)2; PPh3; i-Pr2NEt / dimethylsulfoxide / 1.5 h / 80 °C 16.1: 81 percent / NaOiPr / propan-2-ol / 1 h / 20 °C 17.1: CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 18.1: 7.1 mg / Li2CO3 / dimethylformamide / 14 h / 40 °C 19.1: 48 percent / PPh3; K2CO3; Bu4NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C 20.1: 47 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0 °C 21.1: 96 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C View Scheme
参考文献
Mori, Miwako; Nakanishi, Masato; Kajishima, Daisuke; Sato, Yoshihiro
Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9801 - 9807
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