(1RS,7RS,8RS) methyl 8-chloro-2-oxobicyclo[5.1.0]octano-8-carboxylate

• 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: (1RS,7RS,8RS) methyl 8-chloro-2-oxobicyclo[5.1.0]octano-8-carboxylate
• 英文别名: methyl (1S,7S,8S)-8-chloro-2-oxobicyclo[5.1.0]octane-8-carboxylate
• 化学式: C₁₀H₁₃ClO₃
• 分子量: 216.664
• InChiKey: QTOSJTQINXXCFK-HKPALBBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二氯乙酸甲酯 、 2-环庚烯-1-酮 在 lithium hexamethyldisilazane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (1RS,7RS,8RS) methyl 8-chloro-2-oxobicyclo[5.1.0]octano-8-carboxylate 、 methyl (1R,7R,8S)-8-chloro-2-oxobicyclo[5.1.0]octane-8-carboxylate
  参考文献：
  名称：

  Diastereoselective cyclopropanation of cyclic enones with methyl dichloroacetate anion

  摘要：

  The reaction of alpha,beta -unsaturated cyclic ketones with methyl dichloroacetate anion in the presence of DBU leads to the corresponding bicyclic chlorocyclopropanes in a highly diastereoselective fashion. In the cases of 2-cyclopentenone and 2-cyclohexenone the reaction affords exclusively the endo-Cl isomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00949-8

文献信息

• Diastereoselective cyclopropanation of cyclic enones with methyl dichloroacetate anion
  作者：Ana Escribano、Concepción Pedregal、Rosario González、Alejandro Fernández、Keith Burton、Gregory A Stephenson

  DOI：10.1016/s0040-4020(01)00949-8

  日期：2001.11

  The reaction of alpha,beta -unsaturated cyclic ketones with methyl dichloroacetate anion in the presence of DBU leads to the corresponding bicyclic chlorocyclopropanes in a highly diastereoselective fashion. In the cases of 2-cyclopentenone and 2-cyclohexenone the reaction affords exclusively the endo-Cl isomer. (C) 2001 Elsevier Science Ltd. All rights reserved.