diethyl 2-(2-cyclopropylideneethyl)-2-[(E)-3-phenylprop-2-enyl]propanedioate | 875737-23-8

• 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: diethyl 2-(2-cyclopropylideneethyl)-2-[(E)-3-phenylprop-2-enyl]propanedioate
• CAS: 875737-23-8
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: SJOXOWMUIDOCSS-DHZHZOJOSA-N

物化性质

• 沸点：
  449.6±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-cyclopropylideneethyl)-2-[(E)-3-phenylprop-2-enyl]propanedioate 在 tris(dibenzylideneacetone)dipalladium (0) 抗氧剂168 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以70%的产率得到
  参考文献：
  名称：

  Palladium-Catalyzed [3 + 2] Intramolecular Cycloaddition of Alk-5-enylidenecyclopropanes

  摘要：

  Readily accessible alk-5-enylidenecyclopropanes undergo [3 + 2] intramolecular cycloaddition reactions upon treatment with appropriate palladium complexes. The method allows the rapid and efficient assembly of a variety of bicyclo[3.3.0]octane systems with up to three stereocenters. Preliminary theoretical calculations uncovered previously unsuspected mechanistic possibilities based on either a concerted pallada-ene-like rearrangement or a stepwise process involving zwitterionic intermediates.

  DOI：

  10.1021/ja054487t
• 作为产物：
  描述：

  2-(2-cyclopropylideneethyl)malonate 、 Cinnamyl bromide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到diethyl 2-(2-cyclopropylideneethyl)-2-[(E)-3-phenylprop-2-enyl]propanedioate
  参考文献：
  名称：

  Palladium-Catalyzed [3 + 2] Intramolecular Cycloaddition of Alk-5-enylidenecyclopropanes

  摘要：

  Readily accessible alk-5-enylidenecyclopropanes undergo [3 + 2] intramolecular cycloaddition reactions upon treatment with appropriate palladium complexes. The method allows the rapid and efficient assembly of a variety of bicyclo[3.3.0]octane systems with up to three stereocenters. Preliminary theoretical calculations uncovered previously unsuspected mechanistic possibilities based on either a concerted pallada-ene-like rearrangement or a stepwise process involving zwitterionic intermediates.

  DOI：

  10.1021/ja054487t

文献信息

• Palladium-Catalyzed [3 + 2] Intramolecular Cycloaddition of Alk-5-enylidenecyclopropanes
  作者：Moisés Gulías、Rebeca García、Alejandro Delgado、Luis Castedo、José L. Mascareñas

  DOI：10.1021/ja054487t

  日期：2006.1.1

  Readily accessible alk-5-enylidenecyclopropanes undergo [3 + 2] intramolecular cycloaddition reactions upon treatment with appropriate palladium complexes. The method allows the rapid and efficient assembly of a variety of bicyclo[3.3.0]octane systems with up to three stereocenters. Preliminary theoretical calculations uncovered previously unsuspected mechanistic possibilities based on either a concerted pallada-ene-like rearrangement or a stepwise process involving zwitterionic intermediates.