1-methyl-4-oxobicyclo<3.1.0>-2-hexene-6-carboxylic acid methyl ester | 140701-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-4-oxobicyclo<3.1.0>-2-hexene-6-carboxylic acid methyl ester
• 英文别名: methyl (1S,5S,6R)-1-methyl-4-oxobicyclo[3.1.0]hex-2-ene-6-carboxylate
• CAS: 140701-35-5
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: LUNGVNMCDQQDEY-ZKWXMUAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  1-methyl-2-(trimethylsilyl)cyclopropene-3-carboxylic acid methyl ester 在 potassium fluoride 、 二苯并-18-冠醚-6 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 16.0h， 生成 1-methyl-4-oxobicyclo<3.1.0>-2-hexene-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Reactions of [2+2+1]-cycloaddition with the participation of cyclopropenes and dicobalt hexacarbonyl complexes of acetylenes

  摘要：

  The reaction of dicobalt hexacarbonyl complexes of acetylene and its phenyl and dimethyl derivatives with the methyl ester of 1-methyl-2-(trimethylsilyl)-1-cyclopropene-3-carboxylic acid with adsorption on a silica gel or NaX zeolite surface leads to the formation of a mixture of bicyclo[3.1.0]hex-2-en-4-one and tricyclo[4.1.0.0(2, 4)]heptan-5-one derivatives, whereby the yields and the composition of products are dependent on the type of the adsorbent. It has been found that under the reaction conditions partial isomerization of the bicyclo[3.1.0]hex-2-en-4-one derivatives into substituted phenols occurs. Action of anhydrous KF and crown-ether in acetonitrile on the bicyclo[3.1.0]hex-2-en-4-one derivatives in acetonitrile leads to protodesilylation.

  DOI：

  10.1007/bf00961045