Ethyl 4,5-Benzo-exo-7-benzoyl-3-oxa-2-oxo-cis-bicyclo<4.1.0>hept-4-en-1-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 4,5-Benzo-exo-7-benzoyl-3-oxa-2-oxo-cis-bicyclo<4.1.0>hept-4-en-1-carboxylate
• 英文别名: ethyl (1S,1aS,7bR)-1-benzoyl-2-oxo-1,7b-dihydrocyclopropa[c]chromene-1a-carboxylate
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: AQXITVPPUBJQCV-YRNRMSPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香豆素-3-羧酸乙酯 、 2-溴苯乙酮 在 苄基三苯基氯化膦 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 Ethyl 4,5-Benzo-endo-7-benzoyl-3-oxa-2-oxo-cis-bicyclo<4.1.0>hept-4-en-1-carboxylate 、 Ethyl 4,5-Benzo-exo-7-benzoyl-3-oxa-2-oxo-cis-bicyclo<4.1.0>hept-4-en-1-carboxylate
  参考文献：
  名称：

  Cyclopropanation reaction of 3-Acyl-2H-1-benzopyran-2-ones with phenacylbromide in phase transfer systems

  摘要：

  3-Acyl-2H-1-benzopyran-2-ones 1 reacted with phenacylbromide in the presence of a base to give the cyclopropane derivatives 2 and 3 in moderate yields. The yields of the reaction products were substantially improved by using a catalyst (Aliquat 336 or TPBP) under phase-transfer conditions. A mechanistic explanation is given for the stereoselectivity of these reactions. Spectroscopic data for compounds 2 and 3 are also given.

  DOI：

  10.1016/s0040-4020(01)80371-9

文献信息

• Cyclopropanation reaction of 3-Acyl-2H-1-benzopyran-2-ones with phenacylbromide in phase transfer systems
  作者：Anka Bojilova、Antoaneta Trendafilova、Christo Ivanov、Nestor A Rodios

  DOI：10.1016/s0040-4020(01)80371-9

  日期：1993.3

  3-Acyl-2H-1-benzopyran-2-ones 1 reacted with phenacylbromide in the presence of a base to give the cyclopropane derivatives 2 and 3 in moderate yields. The yields of the reaction products were substantially improved by using a catalyst (Aliquat 336 or TPBP) under phase-transfer conditions. A mechanistic explanation is given for the stereoselectivity of these reactions. Spectroscopic data for compounds 2 and 3 are also given.