(E)-3-(4-bromophenyl)-2-cyano-N-cyclohexylprop-2-enamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-bromophenyl)-2-cyano-N-cyclohexylprop-2-enamide
• 化学式: C₁₆H₁₇BrN₂O
• 分子量: 333.228
• InChiKey: VRNWIWGSVXAPLC-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-bromophenyl)-2-cyano-N-cyclohexylprop-2-enamide 、 二溴丙二酸二乙酯 在 锌 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以78%的产率得到6-(4-bromophenyl)-5-cyano-3-cyclohexyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  基于修饰的重整反应，合成6-芳基-5-氰基-2,4-二氧代-3-氮杂双环[3.1.0]己烷-1-甲酸的3-取代的乙酯

  摘要：

  DOI：

  10.1007/s10593-006-0038-x

文献信息

• Reaction of the zinc enolate derived from 1,1-dibromo-3,3-dimethylbutan-2-one with 3-aryl-2-cyanopropenoic acid amides and esters and 2-oxochromene-3-carboxamides
  作者：V. V. Shchepin、P. S. Silaichev、Yu. G. Stepanyan、K. P. Lebedev、M. I. Vakhrin

  DOI：10.1134/s107036320605015x

  日期：2006.5

  Zinc enolate derived from 1,1-dibromo-3,3-dimethylbutan-2-one reacts with 3-aryl-2-cyanoprop2-enamides and aryl 3-aryl-2-cyanoprop-2-enoates to give the corresponding derivatives of 3-aryl-2-(2,2-dimethylpropanoyl)-1-cyanocyclopropane-1-carboxylic acid as a single stereoisomer with cis arrangement of the hydrogen atoms at the cyclopropane ring. The reactions of the same zinc enolate with 3-morpholinocarbonyl-2H-chromen-2-one and 2-morpholinocarbonyl-3H-benzo[f]chromen-3-one lead to formation of 1-(2,2dimethylpropanoyl)-1a-morpholinocarbonyl-1a,7b-dihydrocyclopropa[c]chromen-2-one and 1-(2,2-dimethylpropanoyl)-1a-morpholinocarbonyl-1a,9c-dihydrobenzo[f]cyclopropa[c]chromen-2-one, respectively as a single stereoisomer.
• Reactions of organozinc reagents derived from dialkyl 2,2-dibromomalonates with 3-aryl-2-cyanoprop-2-enamides
  作者：V. V. Shchepin、P. S. Silaichev、Yu. G. Stepanyan、M. I. Vakhrin

  DOI：10.1134/s1070363206060156

  日期：2006.6

  Organozinc compounds obtained by treatment of dialkyl 2,2-dibromomalonates with metallic zinc reacted with N-substituted 3-aryl-2-cyanoprop-2-enoic acid amides to give alkyl 3-R-6-aryl-5-cyano-2,4-dioxo-3-azabicyclo[3.1.0]hexane-1-carboxamides as a single stereoisomer.
• Reaction of organozinc reagents prepared from bromomalonic acid esters and zinc with 3-aryl-2-cyanopropenoic acid primary amides
  作者：V. V. Shchepin、P. S. Silaichev、Yu. G. Stepanyan、N. Yu. Russkikh、M. I. Vakhrin、M. A. Ezhikova、M. I. Kodess

  DOI：10.1134/s1070428006110054

  日期：2006.11

  Organozinc compounds prepared from bromomalonic acid esters and zinc react with 3-aryl-2-cyanopropenoic acid primary amides giving a single diastereomer of the corresponding 1-R'-4-aryl-2,6-dioxo-5-cyanopiperidine-3-carboxylic acid esters, or 3-R'-6-aryl-2,4-dioxo-5-cyano-3-azabicyclo[3.1.0]hexene-1-carboxylic acid esters.