2-(cyanomethyl)-3-oxo-N-m-tolylbutanamide

• 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: 2-(cyanomethyl)-3-oxo-N-m-tolylbutanamide
• 英文别名: 2-(cyanomethyl)-N-(3-methylphenyl)-3-oxobutanamide
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: ATADYQFJDNQEQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(cyanomethyl)-3-oxo-N-m-tolylbutanamide 在 tin(IV) chloride pentahydrate 作用下， 以 xylene 为溶剂， 反应 8.0h， 生成 (3aRS,9bSR)-7,9b-dimethyl-3,3a-dihydro-1H-pyrrolo[3,2-c]quinoline-2,4(5H,9bH)-dione 、 (3aRS,9bSR)-9,9b-dimethyl-3,3a-dihydro-1H-pyrrolo[3,2-c]quinoline-2,4(5H,9bH)-dione
  参考文献：
  名称：

  One-Step Synthesis of the Tricyclic Core of Martinellic Acid from 2-(Cyanomethyl)-3-oxo-N-arylbutanamides

  摘要：

  [Graphics]A SnCl4 center dot 5H(2)O-mediated facile and efficient one-step synthesis of the tricyclic core of martinellic acid from readily available 2-(cyanomethyl)-3-oxo-N-arylbutanamides was developed and a mechanism involving consecutive hydrolysis of a cyano group and a double annulation process is proposed.

  DOI：

  10.1021/jo701551f
• 作为产物：
  描述：

  3-氧代-N-邻甲苯丁胺 、 溴乙腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到2-(cyanomethyl)-3-oxo-N-m-tolylbutanamide
  参考文献：
  名称：

  One-Step Synthesis of the Tricyclic Core of Martinellic Acid from 2-(Cyanomethyl)-3-oxo-N-arylbutanamides

  摘要：

  [Graphics]A SnCl4 center dot 5H(2)O-mediated facile and efficient one-step synthesis of the tricyclic core of martinellic acid from readily available 2-(cyanomethyl)-3-oxo-N-arylbutanamides was developed and a mechanism involving consecutive hydrolysis of a cyano group and a double annulation process is proposed.

  DOI：

  10.1021/jo701551f

文献信息

• One-Step Synthesis of the Tricyclic Core of Martinellic Acid from 2-(Cyanomethyl)-3-oxo-<i>N</i>-arylbutanamides
  作者：Zhiguo Zhang、Qian Zhang、Zihong Yan、Qun Liu

  DOI：10.1021/jo701551f

  日期：2007.12.1

  [Graphics]A SnCl4 center dot 5H(2)O-mediated facile and efficient one-step synthesis of the tricyclic core of martinellic acid from readily available 2-(cyanomethyl)-3-oxo-N-arylbutanamides was developed and a mechanism involving consecutive hydrolysis of a cyano group and a double annulation process is proposed.