N-(3-chloro-4-methylphenyl)itaconimide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(3-chloro-4-methylphenyl)itaconimide
• 英文别名: 1-(3-chloro-4-methylphenyl)-3-methylidenepyrrolidine-2,5-dione
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: JZAKBBAHEXKYPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-chloro-4-methylphenyl)itaconimide 在 溴 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 (1R,3R)-1-Bromo-5-(3-chloro-4-methyl-phenyl)-4,6-dioxo-5-aza-spiro[2.4]heptane-1-carboxylic acid methyl ester
  参考文献：
  名称：

  脂肪族重氮化合物的反应：V.重氮乙酸甲酯与衣康酸酰亚胺的反应

  摘要：

  Methyl diazoacetate regioselectively adds to N-substituted imides of itaconic acid to afford 2-pyrazolines, methyl 7-aryl-6,8-dioxo-1,2,7-triazaspiro[4.4]non-2-ene-3-carboxylates that in reaction with halogens (Cl-2, Br-2) yield methyl 5-aryl-1-halo-4,6-dioxo-5-azaspiro[2.4]heptane-1-carboxylates as a mixture of syn- and anti$(2$)-isomers.

  DOI：

  10.1023/a:1015534221121

文献信息

• Cascade recyclization of N-arylitaconimides as a new approach to the synthesis of polyfunctional octahydroquinolines
  作者：Yurii A. Kovygin、Khidmet S. Shikhaliev、Mikhail Yu. Krysin、Andrei Yu. Potapov、Irina V. Ledenyova、Yevgeniya A. Kosheleva、Dmitriy Yu. Vandyshev

  DOI：10.1007/s10593-019-02530-5

  日期：2019.8

  A new variant of Hantzsch reaction was developed for the synthesis of 1,2,3,4,5,6,7,8-octahydroquinolines on the basis of regioselective cascade recyclization of N-arylitaconimides in reactions with 3-aminocyclohex-2-enones. The mechanism of this domino process included С-nucleophilic addition of enaminone to the activated multiple bond of itaconimide and intramolecular transamidation with simultaneous

  开发了Hantzsch反应的新变体，用于在与3-氨基环己基-2-烯酮反应的N-芳基itaconimides的区域选择性级联环化的基础上合成1,2,3,4,5,6,7,8-八氢喹啉。该多米诺过程的机理包括将烯胺酮进行亲核加成到衣康酰亚胺的活化的多键上，并进行分子内转酰胺基化，同时使中间体再循环。
• Recyclization of N-arylitaconimides with hydrazines as a new effective synthesis of 2-(3-oxopyrazolidin-4-yl)acetanilides
  作者：Yuri A. Kovygin、Irina S. Zotova、Nikita M. Sotnikov、Vladimir A. Polikarchuk、Khidmet S. Shikhaliev

  DOI：10.1016/j.mencom.2024.02.040

  日期：2024.3

  -arylitaconimides with hydrazine in dioxane at room temperature selectively leads to 2-(3-oxopyrazolidin- 4-yl)acetanilide derivatives in moderate to good yields. The similar reaction with phenylhydrazine proceeds with the simultaneous formation of isomeric 3- and 5-oxo- 1-phenylpyrazolidine-containing acetanilides.

  在室温下，在二恶烷中，用肼将α-芳基衣康酰亚胺再环化，以中等至良好的收率选择性地生成2-(3-氧代吡唑烷-4-基)乙酰苯胺衍生物。与苯肼的类似反应同时形成含有异构体3-和5-氧代-1-苯基吡唑烷的乙酰苯胺。
• Efficient Synthesis of Pyrido[2,3-d]pyrimidines by Recyclization of N-Arylitaconimides with Aminopyrimidinones
  作者：Y. U. Shmoylova、Yu. A. Kovygin、D. Yu. Vandyshev、I. V. Ledenyova、E. A. Kosheleva、Kh. S. Shikhaliev

  DOI：10.1134/s107042802009002x

  日期：2020.9

  A convenient method has been proposed for the synthesis of 2-(4,7-dioxopyrido[2,3-d]pyrimidin-6-yl)acetanilides and 2-(2,4,7-trioxopyrido[2,3-d]pyrimidin-6-yl)acetanilides via reaction ofN-arylitaconimides with 6-aminopyrimidin-4(3H)-ones and 6-aminopyrimidine-2,4(1H,3H)-diones, respectively, in boiling acetic acid.
• Synthesis of new tetrahydropyrido[1,2-a]benzimidazoles based on recyclization of N-arylitaconimides with 2-cyanomethylbenzimidazole
  作者：Yana Yu. Shmoylova、Yuri A. Kovygin、Irina V. Ledenyova、Mikhail A. Prezent、Sergey V. Baranin、Khidmet S. Shikhaliev

  DOI：10.1016/j.mencom.2021.03.037

  日期：2021.3
• ——
  作者：A. P. Molchanov、A. V. Stepakov、R. R. Kostikov

  DOI：10.1023/a:1015534221121

  日期：——

  Methyl diazoacetate regioselectively adds to N-substituted imides of itaconic acid to afford 2-pyrazolines, methyl 7-aryl-6,8-dioxo-1,2,7-triazaspiro[4.4]non-2-ene-3-carboxylates that in reaction with halogens (Cl-2, Br-2) yield methyl 5-aryl-1-halo-4,6-dioxo-5-azaspiro[2.4]heptane-1-carboxylates as a mixture of syn- and anti$(2$)-isomers.