(Z)-3-((S)-1-Phenyl-ethylcarbamoyl)-acrylic acid | 33139-84-3

• 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: (Z)-3-((S)-1-Phenyl-ethylcarbamoyl)-acrylic acid
• 英文别名: (Z)-4-oxo-4-[[(1S)-1-phenylethyl]amino]but-2-enoic acid
• CAS: 33139-84-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: YBCNEBVTRKGSFM-FUOZMLNRSA-N

物化性质

• 沸点：
  462.6±45.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-((S)-1-Phenyl-ethylcarbamoyl)-acrylic acid 在 六甲基二硅氮烷 、 zinc dibromide 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (S)-(-)-N-(1-苯基乙基)顺丁烯二酰亚胺
  参考文献：
  名称：

  Lewis Acid and Hexamethyldisilazane-Promoted Efficient Synthesis of N-Alkyl- and N-Arylimide Derivatives

  摘要：

  DOI：

  10.1021/jo962202c
• 作为产物：
  描述：

  马来酸酐 、 R(+)-alpha-甲基苄胺 以 苯 为溶剂， 反应 1.0h， 生成 (Z)-3-((S)-1-Phenyl-ethylcarbamoyl)-acrylic acid
  参考文献：
  名称：

  Lewis Acid and Hexamethyldisilazane-Promoted Efficient Synthesis of N-Alkyl- and N-Arylimide Derivatives

  摘要：

  DOI：

  10.1021/jo962202c

文献信息

• Rapid and Facile Synthesis of Isomaleimides: Dehydration of Maleamic Acids using Methanesulfonyl Chloride
  作者：Mitchell P. Croatt、Khyarul Alam、Elvis C. McFee

  DOI：10.1055/s-0041-1737414

  日期：2022.7

  The dehydration of maleamic acids using methanesulfonyl chloride as a dehydrating agent to selectively and rapidly (<15 min) generate isomaleimides is reported. A variety of maleamic acid derivatives produce the corresponding isomaleimides in good to excellent yields. Adaptation of this protocol under flow synthesis allows for similar efficiency and decreased reaction times (13 seconds residence time)

  报道了使用甲磺酰氯作为脱水剂对马来酸进行脱水，以选择性和快速（<15 分钟）生成异马来酰亚胺。多种马来酸衍生物以良好至优异的产率生产相应的异马来酰亚胺。在流动合成下对该协议的适应允许类似的效率和减少的反应时间（13 秒的停留时间）。还可以在两步、一瓶操作中将马来酸酐转化为所需的异马来酰亚胺。
• Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines
  作者：Kyohei Tokioka、Satoshi Masuda、Tomomi Fujii、Yasuo Hata、Yukio Yamamoto

  DOI：10.1016/s0957-4166(96)00473-9

  日期：1997.1

  Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C-2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization
  作者：Abderrahim Chihab-Eddine、Adam Daı̈ch、Abderrahim Jilale、Bernard Decroix

  DOI：10.1016/s0040-4039(00)02037-2

  日期：2001.1

  Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by pi -cationic cyclination of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.