2-benzoyl-1-cyano-2-methyl-N-(3-methylphenyl)-3-phenylcyclopropane-1-carboxamide

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: 2-benzoyl-1-cyano-2-methyl-N-(3-methylphenyl)-3-phenylcyclopropane-1-carboxamide
• 英文别名: (1R,2R,3S)-2-benzoyl-1-cyano-2-methyl-N-(3-methylphenyl)-3-phenylcyclopropane-1-carboxamide
• 化学式: C₂₆H₂₂N₂O₂
• 分子量: 394.473
• InChiKey: ACLHWTNOKIPEGY-HRNNMHKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-2-cyano-N-(3-methylphenyl)-3-phenylprop-2-enamide 、 2,2-dibromo-1-phenylpropan-1-one 在 锌 、 溶剂黄146 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.5h， 以67%的产率得到2-benzoyl-1-cyano-2-methyl-N-(3-methylphenyl)-3-phenylcyclopropane-1-carboxamide
  参考文献：
  名称：

  Cyclopropanation of N-substituted 3-aryl-2-cyanoprop-2-enamides and derivatives of 5,5-Dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid and 2-oxochromene-3-carboxylic acid with bromine-containing zinc enolates

  摘要：

  Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-substituted 3-aryl-2-cyanoprop-2-enamides and 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic and 2-oxochromene-3-carboxylic acid derivatives to give, respectively, N-substituted 2-alkyl-3-aryt-2-aroyl-1-cyanocyclopropane-1-carboxamides, 6-(4-bromobenzoyi)-4,4,6-trimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester and morpholide, and 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxylic acids as a single geometric isomer. Treatment of 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-la-carboxylic acids with carboxylic acid anhydrides leads to the formation of the corresponding 9c-alkyl-1-aryl-3,4-dioxo-9b,9c-dihydro-2,5-dioxacyclopenta[2,3]cyclopropa[1,2-a]naphthalen-1-yl carboxylates.

  DOI：

  10.1134/s1070428006070086

文献信息

• Cyclopropanation of N-substituted 3-aryl-2-cyanoprop-2-enamides and derivatives of 5,5-Dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid and 2-oxochromene-3-carboxylic acid with bromine-containing zinc enolates
  作者：V. V. Shchepin、P. S. Silaichev、Yu. G. Stepanyan、M. M. Kalyuzhnyi、N. Yu. Russkikh、M. I. Kodess

  DOI：10.1134/s1070428006070086

  日期：2006.7

  Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-substituted 3-aryl-2-cyanoprop-2-enamides and 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic and 2-oxochromene-3-carboxylic acid derivatives to give, respectively, N-substituted 2-alkyl-3-aryt-2-aroyl-1-cyanocyclopropane-1-carboxamides, 6-(4-bromobenzoyi)-4,4,6-trimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester and morpholide, and 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxylic acids as a single geometric isomer. Treatment of 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-la-carboxylic acids with carboxylic acid anhydrides leads to the formation of the corresponding 9c-alkyl-1-aryl-3,4-dioxo-9b,9c-dihydro-2,5-dioxacyclopenta[2,3]cyclopropa[1,2-a]naphthalen-1-yl carboxylates.