2-(2-cyclopropylideneethyl)-2-(4-oxopent-2-ynyl)malonic acid diethyl ester | 875737-27-2

• 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-cyclopropylideneethyl)-2-(4-oxopent-2-ynyl)malonic acid diethyl ester
• CAS: 875737-27-2
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: JRVXCIBVGFAHPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(2-cyclopropylideneethyl)-2-(4-oxopent-2-ynyl)malonic acid diethyl ester 在 Lindlar's catalyst 、 tris(dibenzylideneacetone)dipalladium (0) 喹啉 、 三异丙基亚磷酸酯 、 氢气 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 (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 正丁基锂 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-(2-cyclopropylideneethyl)-2-(4-oxopent-2-ynyl)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