5-Phenylimino-3-methyl-2,5-dihydrofuran-2-one | 75066-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-Phenylimino-3-methyl-2,5-dihydrofuran-2-one
• 英文别名: 3-methyl-5-phenylimino-5H-furan-2-one；2-Methyl-N-phenylmaleinisoimid；2(5H)-Furanone, 3-methyl-5-(phenylimino)-；3-methyl-5-phenyliminofuran-2-one
• CAS: 75066-65-8
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: GAEZDJPCIUSYAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C(Solv: benzene (71-43-2); ethyl ether (60-29-7))
• 沸点：
  292.8±23.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Phenylimino-3-methyl-2,5-dihydrofuran-2-one 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 2-甲基-N-苯基马来酰亚胺
  参考文献：
  名称：

  Bestmann, Hans Juergen; Schade, Gerold; Luetke, Harry, Chemische Berichte, 1985, vol. 118, # 7, p. 2640 - 2658

  摘要：

  DOI：
• 作为产物：
  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

文献信息

• Bestmann, Hans Juergen; Schade, Gerold; Schmid, Guenther, Angewandte Chemie, 1980, vol. 92, # 10, p. 856 - 858
  作者：Bestmann, Hans Juergen、Schade, Gerold、Schmid, Guenther

  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.
• Bestmann, Hans Juergen; Schade, Gerold; Luetke, Harry, Chemische Berichte, 1985, vol. 118, # 7, p. 2640 - 2658
  作者：Bestmann, Hans Juergen、Schade, Gerold、Luetke, Harry、Moenius, Thomas

  DOI：——

  日期：——
• Cyanuric chloride: decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides
  作者：Kishan P. Haval、Santosh B. Mhaske、Narshinha P. Argade

  DOI：10.1016/j.tet.2005.10.027

  日期：2006.1

  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.