methyl (E)-2-benzylidenecyclopropanecarboxylate | 1415418-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (E)-2-benzylidenecyclopropanecarboxylate
• CAS: 1415418-92-6
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: HFGNHIJWUKYNIO-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-chlorobenzylidene)methylamine N-oxide 、 methyl (E)-2-benzylidenecyclopropanecarboxylate 以 甲苯 为溶剂， 反应 70.0h， 以32%的产率得到methyl (1RS,3SR,4RS,7SR)-7-(4-chlorophenyl)-6-methyl-4-phenyl-5-oxa-6-azaspiro[2.4]heptane-1-carboxylate
  参考文献：
  名称：

  Regioselective cycloaddition of C-aryl- and C-carbamoylnitrones to methyl 2-benzylidenecyclopropanecarboxylate

  摘要：

  C-Aryl- and C-carbamoylnitrones reacted with methyl 2-benzylidenecyclopropanecarboxylate in highly regioselective fashion to give the corresponding 1,3-dipolar cycloaddition products, substituted methyl 5-oxa-6-azaspiro[2.4]heptane-1-carboxylates as mixtures of two diastereoisomers.

  DOI：

  10.1134/s1070428012100041
• 作为产物：
  描述：

  丙-1,2-二烯基苯 、 重氮乙酸甲酯 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以23%的产率得到methyl (E)-2-benzylidenecyclopropanecarboxylate
  参考文献：
  名称：

  Regioselective cycloaddition of C-aryl- and C-carbamoylnitrones to methyl 2-benzylidenecyclopropanecarboxylate

  摘要：

  C-Aryl- and C-carbamoylnitrones reacted with methyl 2-benzylidenecyclopropanecarboxylate in highly regioselective fashion to give the corresponding 1,3-dipolar cycloaddition products, substituted methyl 5-oxa-6-azaspiro[2.4]heptane-1-carboxylates as mixtures of two diastereoisomers.

  DOI：

  10.1134/s1070428012100041

文献信息

• Methyl (E)-2-(2-phenylcyclopropylidene)acetate: Synthesis, isomerization, and reaction with 1,3-diphenyl-2-benzofuran
  作者：A. P. Molchanov、T. Q. Tran、A. V. Stepakov、V. V. Gurzhii、R. R. Kostikov

  DOI：10.1134/s1070428013040064

  日期：2013.4

  Treatment of 3-methyl-2-phenylcycloprop-2-ene-1-carboxylic acid with potassium tert-butoxide induced its isomerization into trans-2-methylidene-3-phenylcyclopropane-1-carboxylic acid which was converted into methyl ester, and heating of the latter for 1 h in toluene gave methyl (E)-2-(2-phenylcyclopropylidene)acetate. Thermal isomerization of methyl (E)-2-(2-phenylcyclopropylidene)acetate on prolonged heating in toluene afforded 5-methoxy-3-methyl-2-phenylfuran, and the reaction with 1,3-diphenyl-2-benzofuran resulted in [4 + 2]-cycloaddition at the exocyclic double bond.