(2-phenylethyl)fumaric acid | 5469-48-7

• 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: (2-phenylethyl)fumaric acid
• 英文别名: phenethyl-fumaric acid；Phenaethyl-fumarsaeure；(E)-2-(2-phenylethyl)but-2-enedioic acid
• CAS: 5469-48-7
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: IXUQTPTVYFFSHS-CSKARUKUSA-N

物化性质

• 熔点：
  202 °C
• 沸点：
  469.6±45.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-phenylethyl)fumaric acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 25.0 ℃ 、700.0 kPa 条件下， 生成 (S)-1,4-Bis-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenethyl-butane-1,4-dione
  参考文献：
  名称：

  Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives

  摘要：

  Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)-Oppolzer's sultam was observed by analysis of the H-1 NMR spectra of the succinamide mixtures with de's of 77-88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1,4-diols and established that addition of hydrogen takes place selectively on the re-face of 14 fumaramides 1. The stereoselectivity was confirmed by estimating the ee's from the F-19 NMR spectra of the Mosher's diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.023
• 作为产物：
  描述：

  diethyl (2-phenylethyl)fumarate 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 (2-phenylethyl)fumaric acid
  参考文献：
  名称：

  Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives

  摘要：

  Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)-Oppolzer's sultam was observed by analysis of the H-1 NMR spectra of the succinamide mixtures with de's of 77-88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1,4-diols and established that addition of hydrogen takes place selectively on the re-face of 14 fumaramides 1. The stereoselectivity was confirmed by estimating the ee's from the F-19 NMR spectra of the Mosher's diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.023

文献信息

• Method for modifying polyfumaric acid diester
  申请人：NIPPON OIL AND FATS COMPANY, LIMITED

  公开号：EP0192997A2

  公开（公告）日：1986-09-03

  According to the invention, a method for modifying a polyfumaric acid diester is provided. The method comprises subjecting the polyfumaric acid diester to thermal treatment to thereby obtain a polyfumarate having carboxyl groups. ; The polyfumaric acid diester is obtained by polymerizing a fumaric acid diester represented by the following general formula of: wherein R represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms or an organic residue having at least one aromatic ring.

  根据本发明，提供了一种改性聚富马酸二酯的方法。该方法包括将聚富马酸二酯进行热处理，从而获得具有羧基的聚富马酸盐。 聚富马酸二酯是通过聚合由以下通式代表的富马酸二酯而获得的： 其中 R 代表具有 1 至 12 个碳原子的烷基、具有 3 至 12 个碳原子的环烷基或具有至少一个芳香环的有机残基。
• Cordier, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1928, vol. 186, p. 870,871
  作者：Cordier

  DOI：——

  日期：——
• COOKE M. P., TETRAHEDRON LETT., 1981, 22, NO 5, 381-384
  作者：COOKE M. P.

  DOI：——

  日期：——
• Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives
  作者：Samaila Jawaid、Louis J. Farrugia、David J. Robins

  DOI：10.1016/j.tetasy.2004.11.023

  日期：2004.12

  Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)-Oppolzer's sultam was observed by analysis of the H-1 NMR spectra of the succinamide mixtures with de's of 77-88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1,4-diols and established that addition of hydrogen takes place selectively on the re-face of 14 fumaramides 1. The stereoselectivity was confirmed by estimating the ee's from the F-19 NMR spectra of the Mosher's diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form. (C) 2004 Elsevier Ltd. All rights reserved.