3-羟基-5-羰基-1-环戊烯-1-庚酸甲酯合成路线 （共 61 条）
反应条件
1: 1.) Mg, 2.) cuprous iodide / 1.) tetrahydrofuran, reflux, 4.5 h, 2.) -10 deg C, 10 min
2: 87 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 3 h / -78 °C
3: 79 percent / toluene-p-sulphonic acid / CH2Cl2 / 3 h / 0 °C
4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C
5: 100 percent / Jones reagent / acetone / 3.5 h / -20 °C
6: diethyl ether / 1 h
7: 81 percent / H2O, AcOH / tetrahydrofuran / 24 h / Ambient temperature
View Scheme
参考文献
Gill, Melvyn; Rickards, Rodney W.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981 , p. 599 - 606
反应条件
1: 86 percent / silver perchlorate / acetone / 1.) room temp. 50 min; 2.) 50 deg C, 1 h
2: 90 percent / silver acetate, glacialacetic acid, zinc / methanol / 2 h / Heating
View Scheme
参考文献
Naora, Hirokazu; Ohnuki, Takashi; Nakamura, Asao
Bulletin of the Chemical Society of Japan, 1988 , vol. 61, # 7 p. 2401 - 2404
反应条件
1: 70 percent / polyphosphoric acid / 2.5 h / 100 °C
2: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature
3: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature
4: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating
5: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating
6: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature
7: 1.86 g / NaOH / methanol; H2O / 2 h / Heating
8: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C
9: 0.96 g / diethyl ether
10: 0.28 g / AcOH-water-THF (60:25:15) / 8 h / Ambient temperature
View Scheme
参考文献
Thakur, S. B.; Jadhav, K. S.; Bhattacharyya, S. C.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986 , vol. 25, p. 675 - 683
反应条件
1: 1.) H2SO4, H2O2 (28percent w/v), 2.) NaOH / 1.) 40 deg C, 8 h, 2.) MeOH, water, reflux, 5 h
2: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature
3: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C
4: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h
5: 40 g / 10percent aq. NaOH / 4 h / Heating
6: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C
7: 70 percent / polyphosphoric acid / 2.5 h / 100 °C
8: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature
9: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature
10: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating
11: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating
12: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature
13: 1.86 g / NaOH / methanol; H2O / 2 h / Heating
14: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C
15: 0.96 g / diethyl ether
16: 0.28 g / AcOH-water-THF (60:25:15) / 8 h / Ambient temperature
View Scheme
参考文献
Thakur, S. B.; Jadhav, K. S.; Bhattacharyya, S. C.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986 , vol. 25, p. 675 - 683
反应条件
1: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h
2: 40 g / 10percent aq. NaOH / 4 h / Heating
3: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C
4: 70 percent / polyphosphoric acid / 2.5 h / 100 °C
5: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature
6: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature
7: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating
8: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating
9: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature
10: 1.86 g / NaOH / methanol; H2O / 2 h / Heating
11: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C
12: 0.96 g / diethyl ether
13: 0.28 g / AcOH-water-THF (60:25:15) / 8 h / Ambient temperature
View Scheme
参考文献
Thakur, S. B.; Jadhav, K. S.; Bhattacharyya, S. C.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986 , vol. 25, p. 675 - 683
反应条件
1: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature
2: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C
3: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h
4: 40 g / 10percent aq. NaOH / 4 h / Heating
5: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C
6: 70 percent / polyphosphoric acid / 2.5 h / 100 °C
7: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature
8: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature
9: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating
10: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating
11: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature
12: 1.86 g / NaOH / methanol; H2O / 2 h / Heating
13: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C
14: 0.96 g / diethyl ether
15: 0.28 g / AcOH-water-THF (60:25:15) / 8 h / Ambient temperature
View Scheme
参考文献
Thakur, S. B.; Jadhav, K. S.; Bhattacharyya, S. C.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986 , vol. 25, p. 675 - 683
反应条件
1: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C
2: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h
3: 40 g / 10percent aq. NaOH / 4 h / Heating
4: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C
5: 70 percent / polyphosphoric acid / 2.5 h / 100 °C
6: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature
7: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature
8: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating
9: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating
10: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature
11: 1.86 g / NaOH / methanol; H2O / 2 h / Heating
12: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C
13: 0.96 g / diethyl ether
14: 0.28 g / AcOH-water-THF (60:25:15) / 8 h / Ambient temperature
View Scheme
参考文献
Thakur, S. B.; Jadhav, K. S.; Bhattacharyya, S. C.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986 , vol. 25, p. 675 - 683
反应条件
1: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C
2: 70 percent / polyphosphoric acid / 2.5 h / 100 °C
3: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature
4: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature
5: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating
6: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating
7: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature
8: 1.86 g / NaOH / methanol; H2O / 2 h / Heating
9: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C
10: 0.96 g / diethyl ether
11: 0.28 g / AcOH-water-THF (60:25:15) / 8 h / Ambient temperature
View Scheme
参考文献
Thakur, S. B.; Jadhav, K. S.; Bhattacharyya, S. C.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986 , vol. 25, p. 675 - 683
反应条件
1: 40 g / 10percent aq. NaOH / 4 h / Heating
2: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C
3: 70 percent / polyphosphoric acid / 2.5 h / 100 °C
4: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature
5: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature
6: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating
7: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating
8: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature
9: 1.86 g / NaOH / methanol; H2O / 2 h / Heating
10: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C
11: 0.96 g / diethyl ether
12: 0.28 g / AcOH-water-THF (60:25:15) / 8 h / Ambient temperature
View Scheme
参考文献
Thakur, S. B.; Jadhav, K. S.; Bhattacharyya, S. C.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986 , vol. 25, p. 675 - 683
反应条件
1: 1.) Mg, 2.) cuprous iodide / 1.) tetrahydrofuran, reflux, 4.5 h, 2.) -10 deg C, 10 min
2: 87 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 3 h / -78 °C
3: 79 percent / toluene-p-sulphonic acid / CH2Cl2 / 3 h / 0 °C
4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C
5: 100 percent / Jones reagent / acetone / 3.5 h / -20 °C
6: diethyl ether / 1 h
7: 81 percent / H2O, AcOH / tetrahydrofuran / 24 h / Ambient temperature
View Scheme
参考文献
Gill, Melvyn; Rickards, Rodney W.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981 , p. 599 - 606
