5-羟基-2-癸烯酸-δ-内酯合成路线 （共 63 条）
反应条件
1.1: triethylamine / dichloromethane / 3 h / 25 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3 h / 25 °C 3.1: thiophene; n-butyllithium; copper (I) cyanide / tetrahydrofuran; hexane / 1 h / 25 °C / Inert atmosphere 3.2: 4 h / -78 - 25 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran 5.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 3 h / 25 °C View Scheme
参考文献
Oliveira, Juliana M.; R. Freitas, Juliano C.; Comasseto, Joao Valdir; Menezes, Paulo Henrique
Tetrahedron, 2011 , vol. 67, # 16 p. 3003 - 3009
反应条件
1: acetic acid / ethanol; H2O / 4 h / 60 °C 2: HCl / Heating View Scheme
参考文献
Ishikawa, Masashi; Amaike, Masayasu; Itoh, Masamichi; Warita, Yasuhiro; Kitahara, Takeshi
Bioscience, Biotechnology and Biochemistry, 2003 , vol. 67, # 10 p. 2210 - 2214
反应条件
1.1: 74 percent / imidazole / CH2Cl2 / 2 h / 0 °C 2.1: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H2O / CH2Cl2 / 3 h / 20 °C 3.1: 68 percent / 2-iodoxybenzoic acid / dimethylsulfoxide; CH2Cl2 / 2 h / 20 °C 4.1: NaH / tetrahydrofuran / 0 °C 4.2: 85 percent / tetrahydrofuran / 2 h 5.1: p-TsOH / methanol / 0.5 h / 20 °C 5.2: 76 percent / benzene / 1 h / 20 °C View Scheme
参考文献
Sabitha, Gowravaram; Gopal; Yadav
Synthetic Communications, 2007 , vol. 37, # 9 p. 1495 - 1502
反应条件
1.1: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H2O / CH2Cl2 / 3 h / 20 °C 2.1: 68 percent / 2-iodoxybenzoic acid / dimethylsulfoxide; CH2Cl2 / 2 h / 20 °C 3.1: NaH / tetrahydrofuran / 0 °C 3.2: 85 percent / tetrahydrofuran / 2 h 4.1: p-TsOH / methanol / 0.5 h / 20 °C 4.2: 76 percent / benzene / 1 h / 20 °C View Scheme
参考文献
Sabitha, Gowravaram; Gopal; Yadav
Synthetic Communications, 2007 , vol. 37, # 9 p. 1495 - 1502
反应条件
1.1: 68 percent / 2-iodoxybenzoic acid / dimethylsulfoxide; CH2Cl2 / 2 h / 20 °C 2.1: NaH / tetrahydrofuran / 0 °C 2.2: 85 percent / tetrahydrofuran / 2 h 3.1: p-TsOH / methanol / 0.5 h / 20 °C 3.2: 76 percent / benzene / 1 h / 20 °C View Scheme
参考文献
Sabitha, Gowravaram; Gopal; Yadav
Synthetic Communications, 2007 , vol. 37, # 9 p. 1495 - 1502
反应条件
1: 87 percent / imidazole / dimethylformamide / 48 h / Ambient temperature 2: 1) O2 + O3, 2) Me2S / 1) CH2Cl2, -70 deg C, 2) a) -70 deg C -> r.t., b) 40 deg C, 48 h 3: 1) butyllithium / 1) hexanes, THF, r.t., 20 min., 2) THF, 30 min. 4: 86 percent / KOH / methanol / 16 h / Ambient temperature 5: 1) NaHCO3, 2) I2 / 1) CH3CN, 0 deg C, 5 min., 2) 0 deg C, 3 h 7: 87 percent / 40percent aq. HF / acetonitrile / 7 h / 0 °C 8: 92 percent / phosphoryl trichloride, pyridine / 5 h / 65 °C View Scheme
参考文献
Bennett, Frank; Knight, David W.; Fenton, Garry
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 6 p. 1543 - 1547
反应条件
1: 1) O2 + O3, 2) Me2S / 1) CH2Cl2, -70 deg C, 2) a) -70 deg C -> r.t., b) 40 deg C, 48 h 2: 1) butyllithium / 1) hexanes, THF, r.t., 20 min., 2) THF, 30 min. 3: 86 percent / KOH / methanol / 16 h / Ambient temperature 4: 1) NaHCO3, 2) I2 / 1) CH3CN, 0 deg C, 5 min., 2) 0 deg C, 3 h 6: 87 percent / 40percent aq. HF / acetonitrile / 7 h / 0 °C 7: 92 percent / phosphoryl trichloride, pyridine / 5 h / 65 °C View Scheme
参考文献
Bennett, Frank; Knight, David W.; Fenton, Garry
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 6 p. 1543 - 1547
反应条件
1: 1) butyllithium / 1) hexanes, THF, r.t., 20 min., 2) THF, 30 min. 2: 86 percent / KOH / methanol / 16 h / Ambient temperature 3: 1) NaHCO3, 2) I2 / 1) CH3CN, 0 deg C, 5 min., 2) 0 deg C, 3 h 5: 87 percent / 40percent aq. HF / acetonitrile / 7 h / 0 °C 6: 92 percent / phosphoryl trichloride, pyridine / 5 h / 65 °C View Scheme
参考文献
Bennett, Frank; Knight, David W.; Fenton, Garry
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 6 p. 1543 - 1547
反应条件
1: 1) NaHCO3, 2) I2 / 1) CH3CN, 0 deg C, 5 min., 2) 0 deg C, 3 h 3: 87 percent / 40percent aq. HF / acetonitrile / 7 h / 0 °C 4: 92 percent / phosphoryl trichloride, pyridine / 5 h / 65 °C View Scheme
参考文献
Bennett, Frank; Knight, David W.; Fenton, Garry
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 6 p. 1543 - 1547
反应条件
1: 86 percent / KOH / methanol / 16 h / Ambient temperature 2: 1) NaHCO3, 2) I2 / 1) CH3CN, 0 deg C, 5 min., 2) 0 deg C, 3 h 4: 87 percent / 40percent aq. HF / acetonitrile / 7 h / 0 °C 5: 92 percent / phosphoryl trichloride, pyridine / 5 h / 65 °C View Scheme
参考文献
Bennett, Frank; Knight, David W.; Fenton, Garry
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 6 p. 1543 - 1547
