E-methyl β-(cyclohepta-2,4,6-trien-1-yl)acrylate

• 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: E-methyl β-(cyclohepta-2,4,6-trien-1-yl)acrylate
• 英文别名: Propenoic acid, 3-(cycloheptatrien-7-yl)-, methyl ester；methyl (E)-3-cyclohepta-2,4,6-trien-1-ylprop-2-enoate
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: MSIHEDNJVJGAGI-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3,5,7-cyclooctatetraene 、 重氮乙酸甲酯 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 Methyl-bicyclo<6.1.0>nona-2,4,6-trien-9-carboxylat 、 Methyl-bicyclo<6.1.0>nona-2,4,6-trien-9-carboxylat 、 Z-methyl β-(cyclohepta-2,4,6-trien-1-yl)acrylate 、 E-methyl β-(cyclohepta-2,4,6-trien-1-yl)acrylate
  参考文献：
  名称：

  Unusual formation of 7-vinylcycloheptatriene derivatives in the catalytic cyclopropanation of cyclooctatetraene with diazocarbonyl compounds in the presence of rhodium catalysts

  摘要：

  The reaction of cyclooctatetraene with methyl diazoacetate or diazaacetone in the presence of rhodium binuclear complexes gives, besides 9-substituted bicyclo[6.1.0]nona-2,4,6-trienes (mixture of anti- and syn-isomers, total yields 60-75%), isomeric beta-(cyclohepta-2,4,6-trien-1-yl)acrylates or 4-(cyclohepta-2,4,6-trien-1-yl)but-3-en-2-one in 20-34% yields. In the case of methyl diazoacetate, a mixture of E- and Z-isomers in a ratio of similar to 3.5 : 1 was obtained, while diazoacetone gave only E-isomer.

  DOI：

  10.1007/bf02494874

文献信息

• Unusual formation of 7-vinylcycloheptatriene derivatives in the catalytic cyclopropanation of cyclooctatetraene with diazocarbonyl compounds in the presence of rhodium catalysts
  作者：Yu. V. Tomilov、D. N. Platonov、O. M. Nefedov

  DOI：10.1007/bf02494874

  日期：1999.11

  The reaction of cyclooctatetraene with methyl diazoacetate or diazaacetone in the presence of rhodium binuclear complexes gives, besides 9-substituted bicyclo[6.1.0]nona-2,4,6-trienes (mixture of anti- and syn-isomers, total yields 60-75%), isomeric beta-(cyclohepta-2,4,6-trien-1-yl)acrylates or 4-(cyclohepta-2,4,6-trien-1-yl)but-3-en-2-one in 20-34% yields. In the case of methyl diazoacetate, a mixture of E- and Z-isomers in a ratio of similar to 3.5 : 1 was obtained, while diazoacetone gave only E-isomer.