1-Ethyl-4-methyl 2-phenylmaleate | 96238-23-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-Ethyl-4-methyl 2-phenylmaleate
• 英文别名: methyl 3-ethoxycarbonylcinnamate；ethyl (Z)-3-methoxycarbonyl-2-phenylpropenoate；1-O-ethyl 4-O-methyl (Z)-2-phenylbut-2-enedioate
• CAS: 96238-23-2
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: QEIRSZKEHMXTRG-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酰甲酸乙酯 、 膦酰基乙酸甲酯二乙酯 在 sodium hydride 作用下， 生成 1-Ethyl-4-methyl 2-phenylmaleate 、 ethyl (E)-3-methoxycarbonyl-2-phenylpropenoate
  参考文献：
  名称：

  Gregory, Barrie; Hinz, Werner; Jones, R. Alan, Journal of Chemical Research, Miniprint, 1984, # 10, p. 2801 - 2821

  摘要：

  DOI：

文献信息

• X=Y-ZH Compounds as potential 1,3-dipoles. Part 30. Cycloaddition of arylidene imines of α-amino esters to acetylenic dipolarophiles and pyrrole forming rearrangements
  作者：Ronald Grigg、H.Q. Nimal Gunaratne、James Kemp

  DOI：10.1016/s0040-4020(01)96015-6

  日期：1990.1

  α-amino esters undergo cycloaddition to ethyl phenylpropiolate, methyl propiolate and dimethyl acetylenedicarboxylate (ADE) on heating in toluene (110°C)or o-xylene (135- 145°C). The reactions proceed via stereospecific azomethine ylide formation and give single 3-pyrroline cycloadducts in moderate to good yield. Reaction of certain of the imines with 2 mol. of ADE leads to a pyrroles formed by rearrangement

  在甲苯（110°C）或邻二甲苯（135-145°C）加热下，α-氨基酯的亚芳基亚胺与苯丙酸乙酯，丙酸甲酯和乙炔二甲酸二甲酯（ADE）发生环加成反应。该反应通过立体有择的甲亚胺叶立德形成而进行，并以中等至良好的产率得到单个的3-吡咯啉环加合物。某些亚胺与2 mol的反应 ADE的重整导致吡咯形成。讨论了重排的机制。
• Highly specific fragmentation processes of isomeric mixed esters of phenylsuccinic acid under electron impact
  作者：I. Vidavsky、A. Mandelbaum、T. Tamiri、S. Zitrin

  DOI：10.1002/oms.1210260420

  日期：1991.4

  AbstractIsomeric mixed dialkyl phenylsuccinates, PhCH(COOR)CH2COOR′, undergo a highly specific elimination of ROH under electron impact. A deuterium‐labelling study showed that the hydrogen atom from the benzylic position 2 is abstracted in this process. These results suggest the occurrence of a ‘hidden’ hydrogen migration of the benzylic hydrogen atom to the carbonylic oxygen of the remote ester group, followed by the elimination of ROH from the adjacent ester group with the involvement of that hydrogen. Alkoxyl group migrations resulting in the formation of [PhCHOR]+ and [PhCHOR′]+ ions are less specific, although the migration of the remote R′O˙ is significantly preferred in all the pairs of isomers examined. Mechanisms are suggested for the formation of the two ions.
• Gregory, Barrie; Hinz, Werner; Jones, R. Alan, Journal of Chemical Research, Miniprint, 1984, # 10, p. 2801 - 2821
  作者：Gregory, Barrie、Hinz, Werner、Jones, R. Alan、Arques, Jose Sepulveda

  DOI：——

  日期：——