methyl (2E,4E)-5-benzoyloxypenta-2,4-dien-1-yl maleate | 851955-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2E,4E)-5-benzoyloxypenta-2,4-dien-1-yl maleate
• 英文别名: 4-O-[(2E,4E)-5-benzoyloxypenta-2,4-dienyl] 1-O-methyl (Z)-but-2-enedioate
• CAS: 851955-81-2
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: ASYBWJVJUWZZIO-PGWVBPBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2E,4E)-5-benzoyloxypenta-2,4-dien-1-yl maleate 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以44%的产率得到(+/-)-methyl (3aS,6R,7S,7aR)-6-benzoyloxy-1-oxo-3,3a,6,7,7a-hexahydro-7-isobenzofurancarboxylate
  参考文献：
  名称：

  Intramolecular Diels−Alder Reactions of Ester-Linked 1,3,8-Nonatrienes

  摘要：

  Penta-1,3-dienyl acrylates undergo kinetically controlled intramolecular Diels-Alder (lMDA) reactions and DFT calculations (B3LYP/6-31+G(d)) predict stereoselectivities that are in very good agreement with the experimental values. The nature of the diene Cl substituent has virtually no influence upon reactivity or trans/cis-stereoselectivity whereas terminal C9 dienophile substituents have a substantial effect on both the reactivity and stereoselectivity of these IMDA reactions. The TSs highlight contributions from strain in the developing tether-containing ring, and steric and electronic effects between tether and dienophile substituents, thus providing insight into the origins of IMDA reactivity and stereoselectivity.

  DOI：

  10.1021/jo0505829
• 作为产物：
  描述：

  1-(benzoyloxy)-5-hydroxy-1E,3E-pentadiene 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 methyl (2E,4E)-5-benzoyloxypenta-2,4-dien-1-yl maleate
  参考文献：
  名称：

  Intramolecular Diels−Alder Reactions of Ester-Linked 1,3,8-Nonatrienes

  摘要：

  Penta-1,3-dienyl acrylates undergo kinetically controlled intramolecular Diels-Alder (lMDA) reactions and DFT calculations (B3LYP/6-31+G(d)) predict stereoselectivities that are in very good agreement with the experimental values. The nature of the diene Cl substituent has virtually no influence upon reactivity or trans/cis-stereoselectivity whereas terminal C9 dienophile substituents have a substantial effect on both the reactivity and stereoselectivity of these IMDA reactions. The TSs highlight contributions from strain in the developing tether-containing ring, and steric and electronic effects between tether and dienophile substituents, thus providing insight into the origins of IMDA reactivity and stereoselectivity.

  DOI：

  10.1021/jo0505829