1-(methoxycarbonyl)-2-(pentylidene)cyclopropanecarboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(methoxycarbonyl)-2-(pentylidene)cyclopropanecarboxylic acid methyl ester
• 英文别名: dimethyl (2Z)-2-pentylidenecyclopropane-1,1-dicarboxylate
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: AIUNAMBVGMJNPN-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  庚-1,2-二烯 、 2-叠氮丙二酸二甲酯 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 生成 1-(methoxycarbonyl)-2-(pentylidene)cyclopropanecarboxylic acid methyl ester 、 1-(methoxycarbonyl)-2-(pentylidene)cyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  An Efficient Stereoselective Synthesis of 4,5-trans-1,5-cis-3-Oxabicyclo[3.1.0]hexan-2-ones via the Iodolactonization of Alkylidenecyclopropyl Esters

  摘要：

  A highly stereoselective iodolactonization of alkylidenecyclopropyl esters with iodine or N-iodosuccinimide (NIS) in aqueous CH3CN to afford 4,5-trans-1,5-cis-3-oxabicyclo-[3.1.0]hexane-2ones is described. The reaction is very general, accommodating a wide range of substituents. A plausible mechanism that explains the essential role of water in this reaction is proposed.

  DOI：

  10.1021/jo050878e

文献信息

• An Efficient Stereoselective Synthesis of 4,5-<i>trans</i>-1,5-<i>cis</i>-3-Oxabicyclo[3.1.0]hexan-2-ones via the Iodolactonization of Alkylidenecyclopropyl Esters
  作者：Shengming Ma、Lianghua Lu

  DOI：10.1021/jo050878e

  日期：2005.9.1

  A highly stereoselective iodolactonization of alkylidenecyclopropyl esters with iodine or N-iodosuccinimide (NIS) in aqueous CH3CN to afford 4,5-trans-1,5-cis-3-oxabicyclo-[3.1.0]hexane-2ones is described. The reaction is very general, accommodating a wide range of substituents. A plausible mechanism that explains the essential role of water in this reaction is proposed.