1,4-环己二酮单乙二醇缩酮合成路线 （共 270 条）
反应条件
(i) , (ii) (heating), aq. AcOH; Multistep reaction;
参考文献
Green,M.M.; Djerassi,C.
Journal of the American Chemical Society, 1967 , vol. 89, p. 5190 - 5198
反应条件
1: NaBH4 / methanol / 2 h / 0 °C
2: 9.67 g / pyridine / 18 h / 20 °C
View Scheme
参考文献
Braem, Daniel; Siles, Samuel; Guelacar Fazil O.; Buchs, Armand
Organic Mass Spectrometry, 1982 , vol. 17, # 2 p. 102 - 106
反应条件
1: sodium tetrahydroborate / methanol-d1 / 0 °C
2: toluene-4-sulfonic acid / water / |Heating
3: pyridine / 20 °C
View Scheme
参考文献
De Vos, Nils; Maton, Cedric; De Vreese, Peter; Brooks, Neil R.; Binnemans, Koen; Stevens, Christian V.
European Journal of Organic Chemistry, 2013 , # 18 p. 3741 - 3750
反应条件
1: 1.) n-BuLi / 1.) THF, hexane, -100 deg C to -95 deg C, 10 min, 2.) THF, hexane, -100 deg C to -95 deg C, 10 min
2: 94 percent / aq. NaOH / 2-methoxy-ethanol / 15 h / Heating
3: HCl conc. / 4 h / Heating
4: 39 percent / H2, HCl conc. / Pd / dioxane / 20 h / 40 - 48 °C
5: 1.) NaH, 2.) KH / 1.) THF, reflux, 2.) THF, reflux, 2 h
6: 82 percent / diphenyl ether / 4 h / 190 - 205 °C
7: 56 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature
8: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature
9: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature
10: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h
11: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature
View Scheme
参考文献
DeGraw; Christie; Colwell; Sirotnak
Journal of Medicinal Chemistry, 1992 , vol. 35, # 2 p. 320 - 324
反应条件
1: 1) NaH, 2) H2 / 2) Pd/C / 1) THF, 2) EtOH
2: LiAlH4 / diethyl ether
View Scheme
参考文献
Itagaki, Noriaki; Kimura, Mari; Sugahara, Tsutomu; Iwabuchi, Yoshiharu
Organic Letters, 2005 , vol. 7, # 19 p. 4185 - 4188
反应条件
hydrogen; triethylamine; palladium 10 on activated carbon in methanol
T=20°C; P=2585.81 Torr; 2 h;
参考文献
CORTEX PHARMACEUTICALS, INC.
Patent: WO2008/143963 A1, 2008 ;
Location in patent: Page/Page column 55-57 ;
反应条件
1.1: magnesium / tetrahydrofuran
1.2: 0 - 20 °C
2.1: toluene-4-sulfonic acid / benzene / 4 h / |Reflux
3.1: iodine / 2 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
Subba Reddy; Nageshwar Rao; Siva Senkar Reddy; Somaiah; Yadav; Subramanyam, Ravi
Tetrahedron Letters, 2014 , vol. 55, # 5 p. 1049 - 1051
反应条件
1: sodium tetrahydroborate; methanol / 2 h / 20 °C
2: silver(l) oxide / 96 h
3: toluene-4-sulfonic acid; water / tetrahydrofuran / 100 °C
View Scheme
参考文献
AC Immune, S.A.
Patent: US2011/280808 A1, 2011 ;
反应条件
1: trimethylsilylacetylene With n-butyllithium in tetrahydrofuran; hexane
T=-76°C; 1 h;
2: 1,4-cyclohexanedione monoacetal in tetrahydrofuran; hexane
T=-74°C; 2 h;
3: With potassium carbonate in methanol
T=20°C; 2 h;
参考文献
Toray Industries, Inc.; NAKAO, Kaoru; MIYAMOTO, Yohei; YAMADA, Naohiro
Patent: EP2565184 A1, 2013 ;
Location in patent: Paragraph 0334-0336 ;
反应条件
diazoacetic acid ethyl ester in 1,4-dioxane
T=20°C; Addition;
参考文献
Conde, Jose J.; Mendelson, Wilford
Tetrahedron Letters, 2000 , vol. 41, # 6 p. 811 - 814
