(E)-2-cyano-N-(4-methylphenyl)-3-phenylprop-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)-2-cyano-N-(4-methylphenyl)-3-phenylprop-2-enamide
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: SIFISIXUYPJTDE-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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)-2-cyano-N-(4-methylphenyl)-3-phenylprop-2-enamide 、 二溴丙二酸二乙酯 在 锌 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以68%的产率得到ethyl 5-cyano-3-(4-methylphenyl)-2,4-dioxo-6-phenyl-3-azabicyclo[3.1.0]hexene-1-carboxylate
  参考文献：
  名称：

  Reactions of organozinc reagents derived from dialkyl 2,2-dibromomalonates with 3-aryl-2-cyanoprop-2-enamides

  摘要：

  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.

  DOI：

  10.1134/s1070363206060156

文献信息

• Tandem halogenation/Michael-initiated ring-closing reaction of α,β-unsaturated nitriles and activated methylene compounds: one-pot diastereoselective synthesis of functionalized cyclopropanes
  作者：Xiaoqing Xin、Qian Zhang、Yongjiu Liang、Rui Zhang、Dewen Dong

  DOI：10.1039/c4ob00087k

  日期：——

  An efficient one-pot synthetic route to highly substituted cyclopropanes has been developed from readily available α,β-unsaturated nitriles and doubly activated methylene compounds under very mild conditions in a highly diastereoselective manner, which involves halogenation, Michael addition and intramolecular ring-closing reaction sequences.

  已经从易于获得的α，β-不饱和腈和双活化的亚甲基化合物在非常温和的条件下以高度非对映选择性的方式开发了一种高效的一锅合成路线，该路线涉及卤化，迈克尔加成和分子内闭环反应序列。
• 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.
• HASSANEEN, HAMDI M.;FARAG, AHMAD M.;ALGHARIB, MOHAMAD S.;SHAWALI, AHMAD S+, GAZZ. CHIM. ITAL., 118,(1988) N 8, C. 569-572
  作者：HASSANEEN, HAMDI M.、FARAG, AHMAD M.、ALGHARIB, MOHAMAD S.、SHAWALI, AHMAD S+

  DOI：——

  日期：——