(Z)-2,3-Dimethyl-4-oxo-4-benzylaminobut-2-enoic acid | 58349-91-0

• 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)-2,3-Dimethyl-4-oxo-4-benzylaminobut-2-enoic acid
• 英文别名: (2Z)-4-(benzylamino)-2,3-dimethyl-4-oxobut-2-enoic acid；(Z)-4-(benzylamino)-2,3-dimethyl-4-oxobut-2-enoic acid
• CAS: 58349-91-0
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: HOGNYCBPYCMVJR-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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)-2,3-Dimethyl-4-oxo-4-benzylaminobut-2-enoic acid 在 溶剂黄146 作用下， 反应 16.0h， 以1.48 g的产率得到N-benzyl-3,4-dimethylmaleimide
  参考文献：
  名称：

  Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2

  摘要：

  本文描述了一种实用方法，利用H2O2实现对多克规模电子缺失型烯烃（如富马酸二乙酯和N-烷基及N-芳基马来酰亚胺）的选择性顺式二羟基化。在该高效的锰基催化体系中，可在常温常压下，以高转化率（超过1000次）实现反应。该催化剂体系由锰盐、吡啶-2-羧酸、酮和碱在原位制备而成。在优化的条件下，富马酸二乙酯至少可实现1000次转化，仅使用1.5当量的H2O2，产物为唯一的（顺-二醇）d/l-酒石酸二乙酯。对于电子丰富的烯烃，如顺式-环辛烯，该催化剂可提供高效的环氧化作用。

  DOI：

  10.1039/c0ob00102c
• 作为产物：
  描述：

  2,3-二甲基马来酸酐 、 苄胺 以 乙醚 为溶剂， 生成 (Z)-2,3-Dimethyl-4-oxo-4-benzylaminobut-2-enoic acid
  参考文献：
  名称：

  Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2

  摘要：

  本文描述了一种实用方法，利用H2O2实现对多克规模电子缺失型烯烃（如富马酸二乙酯和N-烷基及N-芳基马来酰亚胺）的选择性顺式二羟基化。在该高效的锰基催化体系中，可在常温常压下，以高转化率（超过1000次）实现反应。该催化剂体系由锰盐、吡啶-2-羧酸、酮和碱在原位制备而成。在优化的条件下，富马酸二乙酯至少可实现1000次转化，仅使用1.5当量的H2O2，产物为唯一的（顺-二醇）d/l-酒石酸二乙酯。对于电子丰富的烯烃，如顺式-环辛烯，该催化剂可提供高效的环氧化作用。

  DOI：

  10.1039/c0ob00102c

文献信息

• Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2
  作者：Pattama Saisaha、Dirk Pijper、Ruben P. van Summeren、Rob Hoen、Christian Smit、Johannes W. de Boer、Ronald Hage、Paul L. Alsters、Ben L. Feringa、Wesley R. Browne

  DOI：10.1039/c0ob00102c

  日期：——

  A practical method for the multigram scale selective cis-dihydroxylation of electron deficient alkenes such as diethyl fumarate and N-alkyl and N-aryl-maleimides using H2O2 is described. High turnovers (>1000) can be achieved with this efficient manganese based catalyst system, prepared in situ from a manganese salt, pyridine-2-carboxylic acid, a ketone and a base, under ambient conditions. Under optimized conditions, for diethyl fumarate at least 1000 turnovers could be achieved with only 1.5 equiv. of H2O2 with d/l-diethyl tartrate (cis-diol product) as the sole product. For electron rich alkenes, such as cis-cyclooctene, this catalyst provides for efficient epoxidation.

  本文描述了一种实用方法，利用H2O2实现对多克规模电子缺失型烯烃（如富马酸二乙酯和N-烷基及N-芳基马来酰亚胺）的选择性顺式二羟基化。在该高效的锰基催化体系中，可在常温常压下，以高转化率（超过1000次）实现反应。该催化剂体系由锰盐、吡啶-2-羧酸、酮和碱在原位制备而成。在优化的条件下，富马酸二乙酯至少可实现1000次转化，仅使用1.5当量的H2O2，产物为唯一的（顺-二醇）d/l-酒石酸二乙酯。对于电子丰富的烯烃，如顺式-环辛烯，该催化剂可提供高效的环氧化作用。
• 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.
• Efficient asymmetric hydrogenation of the C–C double bond of 2-methyl- and 2,3-dimethyl-N-phenylalkylmaleimides by Aspergillus fumigatus
  作者：Maximiliano Sortino、Susana Alicia Zacchino

  DOI：10.1016/j.tetasy.2010.02.017

  日期：2010.3

  Eight N-phenylalkylmaleimides (four 2-methyl-N-phenylalkylmaleimides and four 2,3-dimethyl-N-phenylalkylmaleimides with an alkyl chain (CH(2))(n) (n = 1-4) between the imide N and the benzene ring) were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)(3) showed that enantiomeric excesses were >99%. (C) 2010 Elsevier Ltd. All rights reserved.