diethyl 2-[(E)-3-cyanoprop-2-enyl]-2-(2-cyclopropylideneethyl)propanedioate | 875737-48-7

• 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: diethyl 2-[(E)-3-cyanoprop-2-enyl]-2-(2-cyclopropylideneethyl)propanedioate
• CAS: 875737-48-7
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: UJPGNRZKGJYOTQ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-[(E)-3-cyanoprop-2-enyl]-2-(2-cyclopropylideneethyl)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75%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：

  丙二酸二乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 tris(dibenzylideneacetone)dipalladium (0) 、 sodium hydride 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 生成 diethyl 2-[(E)-3-cyanoprop-2-enyl]-2-(2-cyclopropylideneethyl)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.