(2E)-9-羟基-2-癸烯酸合成路线 （共 31 条）
反应条件
1: 1.) 1.55M nBuLi / 1.) THF, hexane, -78 deg C, 5 min; -30 deg C, 5 min, 2.) THF, hexane, -78 deg C, 15 min; r.t., 20 min
2: p-toluenesulfonic acid monohydrate / methanol / 0.08 h / Heating
3: 99 percent / H2 / 5percent Pd/BaSO4 / pyridine; quinoline / 0.67 h / 750.06 Torr
4: 72 percent / diphenyldisulfide / cyclohexane / 1.83 h / Irradiation
5: 99 percent / 2N KOH / ethanol / 0.5 h / Heating
View Scheme
参考文献
Schweitzer, Stefan; Voss, Gundula; Gerlach, Hans
Liebigs Annalen der Chemie, 1994 , # 2 p. 189 - 192
反应条件
1: H2 / Pd-CaCO3 / methanol
2: Na2CO3 / dioxane / 150 °C
3: KBH4 / methanol
View Scheme
参考文献
Eiter,K.
Justus Liebigs Annalen der Chemie, 1962 , vol. 658, p. 91 - 99
反应条件
1: HgSO4*2HgO, H2SO4 / dioxane / Heating
2: H2 / Pd-CaCO3 / methanol
3: Na2CO3 / dioxane / 150 °C
4: KBH4 / methanol
View Scheme
参考文献
Eiter,K.
Justus Liebigs Annalen der Chemie, 1962 , vol. 658, p. 91 - 99
反应条件
1: (i) SOCl2, (ii) Br2, (iii) H2O
2: KOtBu / 2-methyl-propan-2-ol
3: NaI, NaOEt
4: NaBH4, NaOH / methanol
View Scheme
参考文献
Kyskina,A.S. et al.
Journal of Organic Chemistry USSR (English Translation), 1971 , vol. 7, p. 51 - 54
Zhurnal Organicheskoi Khimii, 1971 , vol. 7, p. 51 - 55
反应条件
1: HgSO4, aq. HCO2H
2: NaBH4 / methanol
View Scheme
参考文献
Kovalev,B.G. et al.
Journal of Organic Chemistry USSR (English Translation), 1971 , vol. 7, p. 676 - 678
Zhurnal Organicheskoi Khimii, 1971 , vol. 7, p. 667 - 670
反应条件
1: KOtBu / 2-methyl-propan-2-ol
2: NaI, NaOEt
3: NaBH4, NaOH / methanol
View Scheme
参考文献
Kyskina,A.S. et al.
Journal of Organic Chemistry USSR (English Translation), 1971 , vol. 7, p. 51 - 54
Zhurnal Organicheskoi Khimii, 1971 , vol. 7, p. 51 - 55
反应条件
1: NaI, NaOEt
2: NaBH4, NaOH / methanol
View Scheme
参考文献
Kyskina,A.S. et al.
Journal of Organic Chemistry USSR (English Translation), 1971 , vol. 7, p. 51 - 54
Zhurnal Organicheskoi Khimii, 1971 , vol. 7, p. 51 - 55
反应条件
1: (i) aq. H2SO4, (ii) /BRN= 1751370/, piperidine, Py
2: HgSO4, aq. HCO2H
3: NaBH4 / methanol
View Scheme
参考文献
Kovalev,B.G. et al.
Journal of Organic Chemistry USSR (English Translation), 1971 , vol. 7, p. 676 - 678
Zhurnal Organicheskoi Khimii, 1971 , vol. 7, p. 667 - 670
反应条件
1.1: O3 / methanol; CH2Cl2 / 2 °C
1.2: Me2S / methanol; CH2Cl2 / 16 h / 20 °C
1.3: 67.8 percent / TsOH / CH2Cl2 / 16 h / 20 °C
2.1: 98 percent / KOH / ethanol / 2 h / Heating
3.1: 86 percent / diethyl ether / 0 - 20 °C
4.1: 80 percent / pyridine / 48 h / 2 - 20 °C
5.1: SOCl2 / 0.5 h / 65 - 70 °C
6.1: Br2 / SOCl2 / 5 h / 60 °C
7.1: 6.79 g / 2 h / Heating
8.1: CaCO3 / N,N-dimethyl-acetamide / 2 h / Heating
9.1: 2.47 g / aq. KOH / methanol / 10 h / Heating
View Scheme
参考文献
Kharisov; Botsman; Ishmuratova; Ishmuratov; Tolstikov
Chemistry of Natural Compounds, 2002 , vol. 38, # 2 p. 145 - 148
反应条件
1: 86 percent / diethyl ether / 0 - 20 °C
2: 80 percent / pyridine / 48 h / 2 - 20 °C
3: SOCl2 / 0.5 h / 65 - 70 °C
4: Br2 / SOCl2 / 5 h / 60 °C
5: 6.79 g / 2 h / Heating
6: CaCO3 / N,N-dimethyl-acetamide / 2 h / Heating
7: 2.47 g / aq. KOH / methanol / 10 h / Heating
View Scheme
参考文献
Kharisov; Botsman; Ishmuratova; Ishmuratov; Tolstikov
Chemistry of Natural Compounds, 2002 , vol. 38, # 2 p. 145 - 148
