2-(2-Cyclopropylidene-ethyl)-2-((Z)-4-oxo-pent-2-enyl)-malonic acid diethyl ester | 875737-28-3

• 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: 2-(2-Cyclopropylidene-ethyl)-2-((Z)-4-oxo-pent-2-enyl)-malonic acid diethyl ester
• 英文别名: diethyl 2-(2-cyclopropylideneethyl)-2-[(Z)-4-oxopent-2-enyl]propanedioate
• CAS: 875737-28-3
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: VVLOIDCLCLGQSA-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-Cyclopropylidene-ethyl)-2-((Z)-4-oxo-pent-2-enyl)-malonic acid diethyl ester 在 tris(dibenzylideneacetone)dipalladium (0) 三异丙基亚磷酸酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以78%的产率得到(3aS,4S,6aR)-4-Methoxymethyl-6-methylene-hexahydro-pentalene-2,2-dicarboxylic acid diethyl ester
  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：

  diethyl 2-(2-cyclopropylideneethyl)-2-(prop-2-ynyl)malonate 在 Lindlar's catalyst 喹啉 、 正丁基锂 、 氢气 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 2-(2-Cyclopropylidene-ethyl)-2-((Z)-4-oxo-pent-2-enyl)-malonic acid diethyl ester
  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.