(2E,4E)-3-Ethyl-5-methoxy-penta-2,4-dienoic acid methyl ester | 108044-53-7

• 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: (2E,4E)-3-Ethyl-5-methoxy-penta-2,4-dienoic acid methyl ester
• 英文别名: methyl (2E,4E)-3-ethyl-5-methoxypenta-2,4-dienoate
• CAS: 108044-53-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: JTEVADPGUILLBZ-BSWSSELBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-甲基-2(5H)-呋喃酮 、 (2E,4E)-3-Ethyl-5-methoxy-penta-2,4-dienoic acid methyl ester 以 二氯甲烷 为溶剂， 50.0 ℃ 、1499.99 MPa 条件下， 反应 60.0h， 以65%的产率得到methyl (1R*,2S*,5S*,6R*,9S*)-3-ethyl-5-methoxy-9-methyl-7-oxo-8-oxabicyclo<4.3.0>non-3-ene-2-carboxylate
  参考文献：
  名称：

  Diels-Alder cycloadditions of electron-rich, electron-deficient, and push-pull dienes with cyclic dienophiles: high-pressure-induced reactions and theoretical calculations

  摘要：

  High-pressure-promoted (4 + 2) cycloadditions of cyclic dienophiles (mainly beta-angelica lactone and cyclopentenone) with electron-rich and push-pull hetero-substituted dienes have been investigated. Only one regio- and stereoisomer was obtained in all cases. While these dienophiles reacted smoothly with alkoxy- and (silyloxy)butadiene derivatives, replacement of oxygen by sulfur resulted in a dramatic decrease in the reactivity of the dienes. On the other hand, push-pull dienes exhibited reactivity similar to that of the electron-rich dienes, in that the dienophilicity was not changed substantially by the influence of an electron-withdrawing group. Theoretical calculations of activation enthalpies have been carried out by the semiempirical AM1 method. These values and frontier orbital considerations have permitted us to interpret the experimental results and to establish a relative order of reactivity of the dienes and dienophiles herein studied.

  DOI：

  10.1021/jo00013a012
• 作为产物：
  描述：

  甲氧基甲基三苯基氯化膦 、 (E)-methyhyl 3-formyl-2-pentenoate 在 水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (2E,4Z)-3-Ethyl-5-methoxy-penta-2,4-dienoic acid methyl ester 、 (2E,4E)-3-Ethyl-5-methoxy-penta-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  Approach to the aklavinone series through a new high pressure-induced [bcd → abcd] cycloaddition strategy

  摘要：

  DOI：

  10.1016/s0040-4039(00)83865-4

文献信息

• New approaches to anthracyclinones : the [BCD → ABCD] cycloaddition strategy
  作者：Sylvain Laugraud、André Guingant、Jean d'Angelo

  DOI：10.1016/s0040-4039(00)91603-4

  日期：1992.3

  High pressure-induced Diels-Alder cycloaddition of 9,10-dimethoxy-1,4-anthraquinone.with dienes 5 and 8 led to the expected adducts. These constitute useful intermediates in the synthesis of anthracyclinones.
• Approach to the aklavinone series through a new high pressure-induced [bcd → abcd] cycloaddition strategy
  作者：André Guingant、Jean d'Angelo

  DOI：10.1016/s0040-4039(00)83865-4

  日期：1986.1
• Diels-Alder cycloadditions of electron-rich, electron-deficient, and push-pull dienes with cyclic dienophiles: high-pressure-induced reactions and theoretical calculations
  作者：Vicenc Branchadell、Mariona Sodupe、Rosa M. Ortuno、Antonio Oliva、Domingo Gomez-Pardo、Andre Guingant、Jean D'Angelo

  DOI：10.1021/jo00013a012

  日期：1991.6

  High-pressure-promoted (4 + 2) cycloadditions of cyclic dienophiles (mainly beta-angelica lactone and cyclopentenone) with electron-rich and push-pull hetero-substituted dienes have been investigated. Only one regio- and stereoisomer was obtained in all cases. While these dienophiles reacted smoothly with alkoxy- and (silyloxy)butadiene derivatives, replacement of oxygen by sulfur resulted in a dramatic decrease in the reactivity of the dienes. On the other hand, push-pull dienes exhibited reactivity similar to that of the electron-rich dienes, in that the dienophilicity was not changed substantially by the influence of an electron-withdrawing group. Theoretical calculations of activation enthalpies have been carried out by the semiempirical AM1 method. These values and frontier orbital considerations have permitted us to interpret the experimental results and to establish a relative order of reactivity of the dienes and dienophiles herein studied.