2-氧代-3-苯基丙基膦酸二甲酯合成路线 （共 8 条）
反应条件
1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 0.5 h;
2: phenyl-acetic acid methyl ester in tetrahydrofuran; hexane
T=-78°C; 2.16667 h;
参考文献
APPLIED RESEARCH SYSTEMS ARS HOLDING N.V
Patent: WO2003/103604 A2, 2003 ;
Location in patent: Page 69-70 ;
WO 03/103604 A2
反应条件
1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran; hexane
T=0°C; Metallation; 0.333333 h;
2: N-methoxy-N-methyl-2-phenylacetamide in tetrahydrofuran; hexane
T=-78°C; Substitution; 0.5 h;
3: With hydrogenchloride in water
Hydrolysis;
参考文献
Aucagne, Vincent; Gueyrard, David; Tatibouet, Arnaud; Quinsac, Alain; Rollin, Patrick
Tetrahedron, 2000 , vol. 56, # 17 p. 2647 - 2654
反应条件
1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran; pentane
T=-78°C; 0.5 h; Inert atmosphere;
2: benzyl 2-phenylacetate in tetrahydrofuran; pentane
T=-78°C; 5 h; Inert atmosphere;
参考文献
Meurillon, Maia; Chaloin, Laurent; Perigaud, Christian; Peyrottes, Suzanne
European Journal of Organic Chemistry, 2011 , # 20-21 p. 3794 - 3802
反应条件
1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; Metallation; 0.333333 h;
2: With copper(l) iodide in tetrahydrofuran; hexane
T=-30°C; Metallation; 1.5 h;
3: phenylacetyl chloride in hexane; dichloromethane
T=-40 - 20°C; Substitution;
参考文献
Aucagne, Vincent; Gueyrard, David; Tatibouet, Arnaud; Quinsac, Alain; Rollin, Patrick
Tetrahedron, 2000 , vol. 56, # 17 p. 2647 - 2654
反应条件
1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 1 h; Inert atmosphere;
2: phenylacetic acid, ethyl ester in tetrahydrofuran; hexane
T=-78 - 20°C; 1.5 h; Inert atmosphere;
参考文献
Lu, Yingpeng; Zheng, Changwu; Yang, Yingquan; Zhao, Gang; Zou, Gang
Advanced Synthesis and Catalysis, 2011 , vol. 353, # 17 p. 3129 - 3133
反应条件
oxalyl dichloride; dimethyl sulfoxide; triethylamine
1.) CH2Cl2, -65 deg C, 30 min., 2.) -65 deg C then room temp.; Yield given. Multistep reaction;
参考文献
Coppola, Gary M.
Synthesis, 1988 , # 1 p. 81 - 84
反应条件
1: 1.) n-BuLi / 1.) THF, hexane, -65 deg C, 1 h, 2.) THF, -65 deg C, 1 h
2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -65 deg C, 30 min., 2.) -65 deg C then room temp.
View Scheme
参考文献
Coppola, Gary M.
Synthesis, 1988 , # 1 p. 81 - 84
反应条件
1: methanephosphonic acid dimethyl ester With n-butyllithium
2: phenyl-acetic acid methyl ester
参考文献
Elworthy, Todd R; Kertesz, Denis J; Kim, Woongki; Roepel, Michael G; Quattrocchio-Setti, Lina; Smith, David B; Tracy, Jahari Laurant; Chow, Audrey; Li, Fujun; Brill, Emma R; Lach, Leang K; McGee, Daren; Yang, Diana S; Chiou, San-San
Bioorganic and medicinal chemistry letters, 2004 , vol. 14, # 7 p. 1655 - 1659
