(4Z,6E)-2-((Z)-6-Chloro-5-oxo-hex-3-enyl)-2,9-bis-methoxycarbonyl-deca-4,6-dienedioic acid dimethyl ester | 651325-49-4

• 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: (4Z,6E)-2-((Z)-6-Chloro-5-oxo-hex-3-enyl)-2,9-bis-methoxycarbonyl-deca-4,6-dienedioic acid dimethyl ester
• CAS: 651325-49-4
• 化学式: C₂₂H₂₉ClO₉
• 分子量: 472.92
• InChiKey: DKMUCDLCMLGQOL-IFNVRXKZSA-N

物化性质

• 沸点：
  416.6±45.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  122.27
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (4Z,6E)-2-((Z)-6-Chloro-5-oxo-hex-3-enyl)-2,9-bis-methoxycarbonyl-deca-4,6-dienedioic acid dimethyl ester 在 caesium carbonate 、 对甲苯磺酸 、 cesium iodide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 34.0h， 生成 (4aR,4bR,8aR,10aR)-4-Oxo-1,3,4,4a,4b,5,6,8,8a,10a-decahydro-phenanthrene-2,2,7,7-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  Comparative Effects of Conjugated and Deconjugated Isomeric Enones on the Transannular Diels−Alder Reaction

  摘要：

  [GRAPHICS]Two isomeric cyclic trienones 2 and 3 (with four methyl esters at positions 3 and 10) underwent transannular Diels-Alder (TADA) reaction at very different temperatures. This drastic difference could be traced to the capacity of the enone dienophile to be conjugated or unconjugated at the transition state. Molecular modeling could confirm this explanation. The calculated enone proved to be very distorted in transition state ts2, and the TADA reaction temperature was accordingly much higher than the one corresponding to ts3 in which the enone was flat.

  DOI：

  10.1021/ol035791z
• 作为产物：
  描述：

  (4Z,6E)-2-((Z)-6-Chloro-5-hydroxy-hex-3-enyl)-2,9-bis-methoxycarbonyl-deca-4,6-dienedioic acid dimethyl ester 在 戴斯-马丁氧化剂 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以85%的产率得到(4Z,6E)-2-((Z)-6-Chloro-5-oxo-hex-3-enyl)-2,9-bis-methoxycarbonyl-deca-4,6-dienedioic acid dimethyl ester
  参考文献：
  名称：

  Comparative Effects of Conjugated and Deconjugated Isomeric Enones on the Transannular Diels−Alder Reaction

  摘要：

  [GRAPHICS]Two isomeric cyclic trienones 2 and 3 (with four methyl esters at positions 3 and 10) underwent transannular Diels-Alder (TADA) reaction at very different temperatures. This drastic difference could be traced to the capacity of the enone dienophile to be conjugated or unconjugated at the transition state. Molecular modeling could confirm this explanation. The calculated enone proved to be very distorted in transition state ts2, and the TADA reaction temperature was accordingly much higher than the one corresponding to ts3 in which the enone was flat.

  DOI：

  10.1021/ol035791z