[(E)-4-ethoxy-4-oxobut-2-enyl] (2E,4E)-hexa-2,4-dienoate | 81096-04-0

• 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: [(E)-4-ethoxy-4-oxobut-2-enyl] (2E,4E)-hexa-2,4-dienoate
• CAS: 81096-04-0
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: OKEKPTNLHQZTMV-NFGBADIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  [(E)-4-ethoxy-4-oxobut-2-enyl] (2E,4E)-hexa-2,4-dienoate 生成 (3aR,4R,5R,7aS)-5-Methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  BOECKMAN, R. K.;DEMKO, D. M., J. ORG. CHEM., 1982, 47, N 9, 1789-1792

  摘要：

  DOI：
• 作为产物：
  描述：

  sorbic acid 、 4-溴巴豆酸乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到[(E)-4-ethoxy-4-oxobut-2-enyl] (2E,4E)-hexa-2,4-dienoate
  参考文献：
  名称：

  Stereocontrol in the intramolecular Diels-Alder reaction. 4. A remarkable effect of overlap requirements in the connecting chain

  摘要：

  DOI：

  10.1021/jo00348a046

文献信息

• Unexpected epimerization and stereochemistry revision of IMDA adducts from sorbate-related 1,3,8-nonatrienes
  作者：Jinlong Wu、Haihua Yu、Yan Wang、Xinglong Xing、Wei-Min Dai

  DOI：10.1016/j.tetlet.2007.07.046

  日期：2007.9

  Intramolecular Diels-Alder (IMDA) reaction of two sorbate-related 1,3,8-nonatrienes has been investigated in MeCN at 180 degrees C for 1.5 h under controlled microwave heating. On checking the crude product mixture before purification, partial epimerization of the major adduct was found during the reaction. After column chromatographic purification over silica gel, only two cis adducts were obtained and their structures have been thoroughly established by X-ray crystallographic analysis. It is concluded that the putative major trans adduct predicted by the IMDA reaction mechanism undergoes facile epimerization at high temperature or in the presence of silica gel. Structural revision on the adducts has been made. (C) 2007 Elsevier Ltd. All rights reserved.