2,5-dihydropyrrole-1,3-dicarboxylic acid 3-methyl ester 1-vinyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,5-dihydropyrrole-1,3-dicarboxylic acid 3-methyl ester 1-vinyl ester
• 英文别名: 1-O-ethenyl 3-O-methyl 2,5-dihydropyrrole-1,3-dicarboxylate
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: AHYSCFWDQDTJFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-二苯基异苯并呋喃 、 2,5-dihydropyrrole-1,3-dicarboxylic acid 3-methyl ester 1-vinyl ester 以 四氢呋喃 为溶剂， 反应 24.0h， 以27%的产率得到4,9-epoxy-4,9-diphenyl-2-vinyloxycarbonyl-1,3,3a,4,9,9a-hexahydrobenzo[f]isoindole-3a-carboxylic acid methyl ester
  参考文献：
  名称：

  Diastereoselective Syntheses of New Analogues of the Farnesyltransferase Inhibitor RPR 130401

  摘要：

  The access to several benzo[f]perhydroisoindolic analogues of farnesyltransferase inhibitors from a single dienic precursor is reported. An initial [4 + 2] cycloaddition between diphenylisobenzofuran 6 and pyrrolines 11, 14, and 15 led to either the syn or the anti isomers, depending on the mode of activation of the cycloaddition. The syn diastereomers were isolated in 90% de under 12 kbar at room temperature, while their anti counterparts were obtained with the same selectivity by warming the reaction mixture to 110 degreesC in toluene at atmospheric pressure. Both syn and anti adducts were separately N-deprotected, and the resulting amines reacted with an activated ester derived from the acid (20) to afford the final targets (5). Two new analogues (5a and 5b) of the FT inhibitor RPR 130401 were thus synthesized in a mere three-step synthetic scheme with overall yields from 30 to 60%.

  DOI：

  10.1021/jo049037i
• 作为产物：
  描述：

  氯甲酸乙烯酯 、 1-苄基-2,5-二氢-1H-吡咯-3-羧酸甲酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到2,5-dihydropyrrole-1,3-dicarboxylic acid 3-methyl ester 1-vinyl ester
  参考文献：
  名称：

  Diastereoselective Syntheses of New Analogues of the Farnesyltransferase Inhibitor RPR 130401

  摘要：

  The access to several benzo[f]perhydroisoindolic analogues of farnesyltransferase inhibitors from a single dienic precursor is reported. An initial [4 + 2] cycloaddition between diphenylisobenzofuran 6 and pyrrolines 11, 14, and 15 led to either the syn or the anti isomers, depending on the mode of activation of the cycloaddition. The syn diastereomers were isolated in 90% de under 12 kbar at room temperature, while their anti counterparts were obtained with the same selectivity by warming the reaction mixture to 110 degreesC in toluene at atmospheric pressure. Both syn and anti adducts were separately N-deprotected, and the resulting amines reacted with an activated ester derived from the acid (20) to afford the final targets (5). Two new analogues (5a and 5b) of the FT inhibitor RPR 130401 were thus synthesized in a mere three-step synthetic scheme with overall yields from 30 to 60%.

  DOI：

  10.1021/jo049037i

文献信息

• Diastereoselective Syntheses of New Analogues of the Farnesyltransferase Inhibitor RPR 130401
  作者：Nicolas Pichon、Anne Harrison-Marchand、Patrick Mailliet、Jacques Maddaluno

  DOI：10.1021/jo049037i

  日期：2004.10.1

  The access to several benzo[f]perhydroisoindolic analogues of farnesyltransferase inhibitors from a single dienic precursor is reported. An initial [4 + 2] cycloaddition between diphenylisobenzofuran 6 and pyrrolines 11, 14, and 15 led to either the syn or the anti isomers, depending on the mode of activation of the cycloaddition. The syn diastereomers were isolated in 90% de under 12 kbar at room temperature, while their anti counterparts were obtained with the same selectivity by warming the reaction mixture to 110 degreesC in toluene at atmospheric pressure. Both syn and anti adducts were separately N-deprotected, and the resulting amines reacted with an activated ester derived from the acid (20) to afford the final targets (5). Two new analogues (5a and 5b) of the FT inhibitor RPR 130401 were thus synthesized in a mere three-step synthetic scheme with overall yields from 30 to 60%.