methyl (E)-2-(2-phenylcyclopropylidene)acetate | 1437279-60-1

• 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-(2-phenylcyclopropylidene)acetate
• 英文别名: methyl (2E)-2-(2-phenylcyclopropylidene)acetate
• CAS: 1437279-60-1
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: LXDUSXAAAGZDFR-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-(2-phenylcyclopropylidene)acetate 以 甲苯 为溶剂， 反应 5.0h， 生成 2-methoxy-4-methyl-5-phenylfuran
  参考文献：
  名称：

  Methyl (E)-2-(2-phenylcyclopropylidene)acetate: Synthesis, isomerization, and reaction with 1,3-diphenyl-2-benzofuran

  摘要：

  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.

  DOI：

  10.1134/s1070428013040064
• 作为产物：
  描述：

  丙-1,2-二烯基苯 在 rhodium(II) acetate dimer 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 methyl (E)-2-(2-phenylcyclopropylidene)acetate
  参考文献：
  名称：

  Methyl (E)-2-(2-phenylcyclopropylidene)acetate: Synthesis, isomerization, and reaction with 1,3-diphenyl-2-benzofuran

  摘要：

  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.

  DOI：

  10.1134/s1070428013040064

文献信息

• Acid-Induced Rearrangement of Cycloadducts from Cyclopropenecarboxylates and 1,3-Diarylisobenzofurans
  作者：Mariia M. Efremova、Alexander P. Molchanov、Anna G. Larina、Galina L. Starova、Rafael R. Kostikov、Alexander V. Stepakov

  DOI：10.1002/hlca.201500114

  日期：2016.7

  Treatment of several Diels–Alder adducts of cyclopropenecarboxylates and 1,3‐diarylisobenzofurans with a strong acid triggers a skeletal rearrangement resulting in 4,8b‐dihydro‐3aH‐indeno[1,2‐b]furans.

  用强酸处理几种Diels –环丙烯羧酸酯和1,3-二芳基异苯并呋喃的Alder加合物会引起骨架重排，从而导致4,8b-dihydro-3a H-茚三酮[1,2- b ]呋喃。