diethyl 1-iodo-4-(methylenecyclopropyl)butane-1,1-dicarboxylate | 166879-33-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 1-iodo-4-(methylenecyclopropyl)butane-1,1-dicarboxylate
• 英文别名: Diethyl 2-iodo-2-[3-(2-methylidenecyclopropyl)propyl]propanedioate
• CAS: 166879-33-0
• 化学式: C₁₄H₂₁IO₄
• 分子量: 380.223
• InChiKey: VUFYBJBBXGCQPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1-iodo-4-(methylenecyclopropyl)butane-1,1-dicarboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 、 六正丁基二锡 作用下， 生成 diethyl methylenecycloheptane-2,2-dicarboxylate 、 diethyl 6-(methyl)methylenecyclohexane-2,2-dicarboxylate
  参考文献：
  名称：

  Malonate radical cyclisations of methylenecyclopropane derivatives

  摘要：

  Cyclisations of various methylenecyclopropyl substituted malonate radicals have been studied. Radicals derived from malonates 4 and 9 underwent exclusive 5-exo cyclisation onto the methylenecyclopropane alkene, followed by opening of the resulting cyclopropylmethyl radical, to give methylenecyclohexane products. Radicals derived from malonates 5 and 10 largely gave bicyclo[1.5.0]octane products, in good yields, as a result of 7-endo cyclisation. Cyclisation of the radical derived from malonate 11 gave a bicyclo[1.5.0]nonane derivative in 31% yield, as a result of an 8-endo cyclisation.

  DOI：

  10.1016/s0040-4020(01)89430-8
• 作为产物：
  描述：

  3-(2-methylenecyclopropyl)propan-1-ol 在 N-碘代丁二酰亚胺 、 四溴化碳 、 potassium hydride 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 29.67h， 生成 diethyl 1-iodo-4-(methylenecyclopropyl)butane-1,1-dicarboxylate
  参考文献：
  名称：

  Malonate radical cyclisations of methylenecyclopropane derivatives

  摘要：

  Cyclisations of various methylenecyclopropyl substituted malonate radicals have been studied. Radicals derived from malonates 4 and 9 underwent exclusive 5-exo cyclisation onto the methylenecyclopropane alkene, followed by opening of the resulting cyclopropylmethyl radical, to give methylenecyclohexane products. Radicals derived from malonates 5 and 10 largely gave bicyclo[1.5.0]octane products, in good yields, as a result of 7-endo cyclisation. Cyclisation of the radical derived from malonate 11 gave a bicyclo[1.5.0]nonane derivative in 31% yield, as a result of an 8-endo cyclisation.

  DOI：

  10.1016/s0040-4020(01)89430-8