7-phenylbicyclo[3.1.1]heptane-6,7-carbolactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 7-phenylbicyclo[3.1.1]heptane-6,7-carbolactone
• 英文别名: (2S,6R)-7-phenyl-8-oxatricyclo[4.3.0.02,7]nonan-9-one
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: PTVIARLALXPYHC-KCXRBIIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-phenylbicyclo[3.1.1]heptane-6,7-carbolactone 在 氨 作用下， 以 甲醇 为溶剂， 以96%的产率得到7-hydroxy-7-phenylbicyclo[3.1.1]heptane-6-carboxamide
  参考文献：
  名称：

  Synthesis of 2-Phenyl-3-oxa-5-azatricyclo[4.4.0.0^2,7]decan-4-one

  摘要：

  Cleavage of the lactone ring in 7-phenylbicyclo[3.1.1]heptan-6,7-carbolactone by the action of ammonia and hydrazine and subsequent oxidative cyclization of the resulting hydroxy amide and hydroxy hydrazide gave a cyclic carbamate, 3-oxa-5-azatricyclo[4.4.0.0(2,7)]decan-4-one.

  DOI：

  10.1023/b:rujo.0000019733.86386.70
• 作为产物：
  描述：

  7-phenyltricyclo[4.1.0.0^2,7]heptane-1-carboxylic acid 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到7-phenylbicyclo[3.1.1]heptane-6,7-carbolactone
  参考文献：
  名称：

  Electrophile-Initiated Lactonization of 7-Phenytricyclo[4.1.0.0^2,7]heptane-1-carboxylic Acid

  摘要：

  Treatment of 7-phenyltricyclo[4.1.0.0(2,7)]heptane-1-carboxylic acid with benzenesulfenyl chloride, mercury acetate, and hydrogen chloride leads to cleavage of the central C-C bond in the bicyclobutane fragment and heterocyclization to substituted bicyclo[3.1.1]heptane-6,7-carbolactones.

  DOI：

  10.1023/b:rujo.0000019732.37554.24

文献信息

• Electrophile-Initiated Lactonization of 7-Phenytricyclo[4.1.0.0²^,⁷]heptane-1-carboxylic Acid
  作者：V. V. Razin、R. N. Zolotarev

  DOI：10.1023/b:rujo.0000019732.37554.24

  日期：2003.12

  Treatment of 7-phenyltricyclo[4.1.0.0(2,7)]heptane-1-carboxylic acid with benzenesulfenyl chloride, mercury acetate, and hydrogen chloride leads to cleavage of the central C-C bond in the bicyclobutane fragment and heterocyclization to substituted bicyclo[3.1.1]heptane-6,7-carbolactones.
• Synthesis of 2-Phenyl-3-oxa-5-azatricyclo[4.4.0.0²^,⁷]decan-4-one
  作者：R. N. Zolotarev、V. V. Razin

  DOI：10.1023/b:rujo.0000019733.86386.70

  日期：2003.12

  Cleavage of the lactone ring in 7-phenylbicyclo[3.1.1]heptan-6,7-carbolactone by the action of ammonia and hydrazine and subsequent oxidative cyclization of the resulting hydroxy amide and hydroxy hydrazide gave a cyclic carbamate, 3-oxa-5-azatricyclo[4.4.0.0(2,7)]decan-4-one.