(Z)-2-Methyl-4-oxo-4-phenylaminobut-2-enoic acid | 80818-21-9

• 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: (Z)-2-Methyl-4-oxo-4-phenylaminobut-2-enoic acid
• 英文别名: (Z)-4-anilino-2-methyl-4-oxobut-2-enoic acid
• CAS: 80818-21-9
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: JQAQLLLOJUHUSS-FPLPWBNLSA-N

物化性质

• 沸点：
  443.3±37.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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)-2-Methyl-4-oxo-4-phenylaminobut-2-enoic acid 在 三聚氯氰 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以97%的产率得到5-Phenylimino-3-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  Cyanuric chloride: decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides

  摘要：

  Starting from maleanitic and maleamic acids, a facile general approach to kinetically controlled isomaleimides has been described for the first time using cyanuric chloride as a dehydrating agent with 85-98% yields. The effect of a variety of substituents present on the aromatic ring in amine and maleic anhydride moiety, on these kinetic/thermodynamic dehydration processes of anilic acids has been also described. Under the same set of reaction conditions the phthalanilic acid gave kinetically controlled product, isoplitalimide in 91% yield, while the corresponding succinanilic acid furnished the thermodynamically more stable succinimide in high yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.027
• 作为产物：
  描述：

  3-methyl-3-phenylcarbamoyl-acrylic acid 以 氘代二甲亚砜 为溶剂， 生成 (Z)-2-Methyl-4-oxo-4-phenylaminobut-2-enoic acid
  参考文献：
  名称：

  胺对柠康酸酐的作用。（Z）-2-甲基-3-吡咯烷基羰基丙烯酸的X射线晶体结构

  摘要：

  柠康酸与15种伯胺和仲胺的反应得到了异丁烯二酸（2）和（3）的混合物，其中前者占主导地位。变暖时，更丰富的异构体重排为热力学稳定的N-取代的（Z）-2-甲基-3-氨基甲酰基丙烯酸（3）。通过X射线分析确认了吡咯烷化物（3q）的结构。描述了将吡咯烷化物转化为4-甲基-6-吡咯烷酮-1，3-恶嗪-2-酮（7）的失败尝试。

  DOI：

  10.1039/p19810002890

文献信息

• Synthesis and spectroscopic of triorganostannyl esters of amic acids. Crystal structure of the triphneylstannyl ester of citraconic acid monopyrrolidide
  作者：Areila Samuel-Lewis、Peter J. Smith、John.H. Aupers、David C. Povey

  DOI：10.1016/0022-328x(91)86246-m

  日期：1991.1

  triorganostannyl esters. The 119mSn Mössbauer spectra, at 80 K, show them all to be polymers containing pentacoordinate tin atoms and the infrared data at room temperature indicate that the amido carbonyl groups bridge intermoleculary between planar R3Sn moieties. The polymeric structure of the triphenylstannyl ester of citraconic acid monopyrrolidide has been confirmed by an X-ray study.

  七种酰胺酸与氢氧化三苯锡，氢氧化三环己基锡或双（三丁基锡）氧化物的反应产生了十八种新的三有机锡烷基酯。在80 K下的119m SnMössbauer光谱显示它们都是含有五配位锡原子的聚合物，室温下的红外数据表明酰胺羰基桥连了平面R 3 Sn部分之间的分子间。X射线研究证实了柠康酸单吡咯烷化物的三苯基锡烷基酯的聚合物结构。
• Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides
  作者：YELİZ FATURACI、NECDET COŞKUN

  DOI：10.3906/kim-1203-34

  日期：——

  Itaconic anhydride reacts with aryl amines to give a substituent controlled equilibrium mixture of regioisomeric (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids. Electron-donating groups favor nucleophilic attack on C-5 carbonyl, while the presence of electron-withdrawing groups enhances the bias for attack on C-2 carbonyl. The treatment of (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl_2-Et_3N in THF provided the corresponding maleimides in high yields while under the same conditions the maleic anhydride aryl amine addition products gave predominately the corresponding 3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent dependent ratio.

  伊托酸酐与芳胺反应生成一种取代基控制的区域异构体平衡混合物，包括(Z)-2-甲基-和(Z)-3-甲基-4-氧代-4-(芳胺基)丁-2-烯酸。电子供给基团有利于对C-5羰基的亲核攻击，而电子吸引基团的存在则增强了对C-2羰基攻击的偏好。将(Z)-2-甲基-和(Z)-3-甲基-4-氧代-4-(芳胺基)丁-2-烯酸与SOCl₂-Et₃N在THF中处理，得到相应的马来咪唑，产率较高；而在相同条件下，马来酸酐与芳胺的加成产物主要生成相应的3-氯-1-芳基吡咯烷-2,5-二酮和马来咪唑，比例依赖于取代基。
• Maleamic and Citraconamic Acids, Methyl Esters, and Imides
  作者：NARIMAN B. MEHTA、ARTHUR P. PHILLIPS、(MRS.) FLORENCE FU LUI、RONALD E. BROOKS

  DOI：10.1021/jo01076a038

  日期：1960.6
• Anschuetz, Justus Liebigs Annalen der Chemie, 1928, vol. 461, p. 168
  作者：Anschuetz

  DOI：——

  日期：——
• Product diversity in cyclisations of maleamic acids: the imide–isoimide dichotomy
  作者：John E. T. Corrie、Madeleine H. Moore、Giles D. Wilson

  DOI：10.1039/p19960000777

  日期：——

  Cyclisation of maleamic acids with acetic anhydride in dimethylacetamide (DMA) at ca. 75 degrees C, with or without added cobalt naphthenate, gives predominantly maleimides when the parent maleic anhydride is unsubstituted. However, when the maleic anhydride has either one or two methyl substituents, the products are greater than or equal to 95% maleisoimides (5-imino-2,5-dihydrofuran-2-ones). In contrast all maleamic acids investigated, regardless of the extent of substitution, give exclusively maleimides when heated in acetic acid under reflux. Isoimide formation in the Ac2O-DMA-cobalt naphthenate procedure appears to arise from kinetic control, since the isoimide preference was reduced at higher reaction temperature. The preferred Z-stereochemistry of the isoimide 3 is confirmed by X-ray crystallography.