2-氧代环戊烷羧酸甲酯合成路线 （共 119 条）
反应条件
1: 1.) sodium hydride / 1.) THF, r.t., 20 min, 2.) THF, r.t., 4 h
2: 83 percent / toluene-p-sulphonic acid / benzene / 48 h / Heating
3: 1.) sodium periodate, 2.) CaCO3 / 1.) water, methanol, r.t., 24 h, 2.) toluene, reflux, 16 h
4: 90 percent / tetramethylguanidine / 72 h / Ambient temperature
5: 1.) sodium methoxide, 2.) ammonium acetate, TiCl3 / 1.) methanol, 20 min, 2.) water, 1.5 h, r.t.
6: 79 percent / trifluoroacetic acid; H2O / 6 h / Ambient temperature
View Scheme
参考文献
Hewson, Alan T.; MacPherson, David T.
Tetrahedron Letters, 1983 , vol. 24, # 6 p. 647 - 648
反应条件
sodium hydride
1.)THF, 30 min, 2.)reflux, 12 h; Yield given. Multistep reaction;
参考文献
McBride, Bill J.; Garst, Michael E.; Hopkins, Mark
Journal of Organic Chemistry, 1984 , vol. 49, p. 1824 - 1825
反应条件
1: With potassium carbonate in acetone
12 h; Heating;
2: With potassium cyanide in dimethyl sulfoxide
0.5 h; Heating; Further stages.;
参考文献
Cramer; Harmata; Rashatasakhon
Journal of Organic Chemistry, 2001 , vol. 66, # 16 p. 5641 - 5644
反应条件
1: 95 percent / sodium hydride / dimethylformamide
2: 88 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 5 h / Heating
3: neat (no solvent) / pyrolysis
4: 75.4 percent / toluene-p-sulphonic acid monohydrate / 24 h / Heating
5: water / stannic chloride / CH2Cl2
6: 97 percent / triethylamine / 1 h
View Scheme
参考文献
Evans, Elizabeth H.; Hewson, Alan T.; March, Lorraine A.; Nowell, Ian W.; Wadsworth, Alan H.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987 , p. 137 - 150
反应条件
triethylamine; malonic acid dimethyl ester in toluene
参考文献
Hellmann,H.; Dieterich,D.
Justus Liebigs Annalen der Chemie, 1962 , vol. 656, p. 89 - 96
反应条件
1: K2CO3 / acetone / 48 h / Heating
2: glacial AcOH; 6M HCl / Heating
View Scheme
参考文献
Wang, Shaozhao; Chen, Gang; Kayser, Margaret M.; Iwaki, Hiroaki; Lau, Peter C.K.; Hasegawa, Yoshie
Canadian Journal of Chemistry, 2002 , vol. 80, # 6 p. 613 - 621
反应条件
1.1: potassium carbonate / acetone / 12 h / Reflux; Inert atmosphere
2.1: methanol; sodium methylate / 3 h / Reflux; Inert atmosphere
2.2: 3 h / Reflux; Inert atmosphere
3.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere
3.2: 0 °C / Inert atmosphere
4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 9 h / 0 - 20 °C / Inert atmosphere
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 4 h / 0 °C / Inert atmosphere
6.1: potassium hydroxide / methanol; water / 8 h / 60 °C
6.2: 20 °C / pH 1
7.1: sulfuric acid / dichloromethane; water / 16 h / 0 °C
View Scheme
参考文献
Abraham, Elin; Claridge, Timothy D.W.; Davies, Stephen G.; Odell, Barbara; Roberts, Paul M.; Russell, Angela J.; Smith, Andrew D.; Smith, Lorna J.; Storr, Helen R.; Sweet, Miles J.; Thompson, Amber L.; Thomson, James E.; Tranter, George E.; Watkin, David J.
Tetrahedron Asymmetry, 2011 , vol. 22, # 1 p. 69 - 100
反应条件
1: With sodium hydroxide
2: With hydrogenchloride in water
参考文献
Miller, Chris P.; Bhaket, Pushpal; Muthukaman, Nagarajan; Lyttle, C. Richard; Shomali, Maysoun; Gallacher, Kyla; Slocum, Connie; Hattersley, Gary
Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 24 p. 7516 - 7520
反应条件
ammonium acetate in methanol
参考文献
Raghavan, Subharekha; Tria, G. Scott; Shen, Hong C.; Ding, Fa-Xiang; Taggart, Andrew K.; Ren, Ning; Wilsie, Larrisa C.; Krsmanovic, Mihajlo L.; Holt, Tom G.; Wolff, Michael S.; Waters, M. Gerard; Hammond, Milton L.; Tata, James R.; Colletti, Steven L.
Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 11 p. 3163 - 3167
反应条件
1: potassium tert-butylate / tert-butyl alcohol / |Reflux
2: trichlorophosphate / 3 h / |Reflux
View Scheme
参考文献
Savall, Brad M.; Chavez, Frank; Tays, Kevin; Dunford, Paul J.; Cowden, Jeffery M.; Hack, Michael D.; Wolin, Ronald L.; Thurmond, Robin L.; Edwards, James P.
Journal of Medicinal Chemistry, 2014 , vol. 57, # 6 p. 2429 - 2439
