(E)-N-benzyl-2-cyano-3-phenylacrylamide

• 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)-N-benzyl-2-cyano-3-phenylacrylamide
• 英文别名: (2E)-N-benzyl-2-cyano-3-phenylprop-2-enamide；(E)-N-benzyl-2-cyano-3-phenylprop-2-enamide
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: GUURNUUYOORXRM-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 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)-N-benzyl-2-cyano-3-phenylacrylamide 在 (L)-2-{diphenyl[(triphenylsilyl)oxy]methyl}pyrrolidine 、 间氯过氧苯甲酸 、 对硝基苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  有机催化级联反应：面向多样性的合成氢异喹啉支架的建设。

  摘要：

  提出了由三烯胺介导的具有2，4-二烯丙基的氰基丙烯酰胺的[4 + 2]-环加成/亲核闭环反应级联序列的有机催化对映选择性合成的高功能化氢异喹啉。相应的环加合物以高收率和优异的立体选择性形成。此外，一系列转化证明了所获得的氢异喹啉的合成应用。

  DOI：

  10.1039/c4cc01231c
• 作为产物：
  描述：

  2-氰基-N-(苯基甲基)-乙酰胺 、 苯甲醛 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 以80%的产率得到(E)-N-benzyl-2-cyano-3-phenylacrylamide
  参考文献：
  名称：

  在无金属条件下，由3-取代的2-氰基丙烯酰胺与N-甲苯磺酰hydr高度立体选择性地合成1-氰基环丙烷甲酰胺

  摘要：

  已经成功地开发了具有N-甲苯磺酰hydr的缺电子烯烃3-取代的2-氰基丙烯酰胺的无金属环丙烷化。该策略提供了一种简单的方法，可合成具有四价立体异构中心的非常有价值的1-氰基环丙烷甲酰胺，且产率高，非对映选择性高（在19：1 dr时产率高达90％）。该反应可以以一锅的方式和以克为单位由芳基醛进行。

  DOI：

  10.1016/j.tetlet.2017.05.070

文献信息

• Highly stereoselective synthesis of 1-cyanocyclopropane-carboxamides from 3-substituted-2-cyanoacrylamides with N -tosylhydrazones under metal-free conditions
  作者：Xufeng Nie、Yachuan Wang、Lijun Yang、Zaijun Yang、Tairan Kang

  DOI：10.1016/j.tetlet.2017.05.070

  日期：2017.8

  lamides with N-tosylhydrazones has been successfully developed. This strategy provide a simple route to the synthesis of very valuable 1-cyanocyclopropanecarboxamides with a quaternary stereogenic center in good yields and with high diastereoselectivities (up to 90% yield with 19:1 dr). The reaction could be performed in one-pot fashion and in a gram-scale from aryl aldehydes.

  已经成功地开发了具有N-甲苯磺酰hydr的缺电子烯烃3-取代的2-氰基丙烯酰胺的无金属环丙烷化。该策略提供了一种简单的方法，可合成具有四价立体异构中心的非常有价值的1-氰基环丙烷甲酰胺，且产率高，非对映选择性高（在19：1 dr时产率高达90％）。该反应可以以一锅的方式和以克为单位由芳基醛进行。
• 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.
• One-Pot Synthesis of Optically Enriched 2-Piperidinones from Aliphatic Aldehydes and Cyanoacrylamides
  作者：Ying He、Tai-Ran Kang、Quan-Zhong Liu、Lian-Mei Chen、Yi-Lian Tu、Ya-Jun Liu、Tang-Bin Chen、Zhi-Qiang Wang、Jie Liu、Yong-Mei Xie、Jin-Liang Yang、Long He

  DOI：10.1021/ol401951g

  日期：2013.8.16

  A highly stereoselective one-pot reaction of aliphatic aldehydes and cyanoacrylamides has been developed. The one-pot reaction includes an organocatalytic Michael addition followed by an intramolecular hemiaminalization. After reduction, optically enriched 2-piperidinones with three contiguous chiral centers were obtained in up to 95% yield and 9:1 dr with 99% ee.
• 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.
• Cyclopropanation of 2-arylmethylidenemalononitriles, alkyl 3-aryl-2-cyanoprop-2-enoates, and N-substituted 3-aryl-2-cyanoprop-2-enamides with bromine-containing zinc enolates
  作者：V. V. Shchepin、Yu. G. Stepanyan、P. S. Silaichev、M. A. Ezhikova、M. I. Kodess

  DOI：10.1134/s1070428007070111

  日期：2007.7

  Zinc enolates derived from 2,2-dibromoindan-1-one and 2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one reacted with 2-arylmethylidenemalononitriles, alkyl 3-aryl-2-cyanoprop-2-enoates, and N-substituted 3-aryl-2-cyanoprop-2-enamides to give, respectively, 3-aryl-1'-oxo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-2-2-dicarbonitriles, 3-aryl-1'-oxo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalene]-2,2-dicarbonitriles, alkyl 3-aryl-2-cyano-1'-oxo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-2-carboxylates, alkyl 3-aryl-2-cyano-1'-oxo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalene]-2-carboxylates, and N-substituted 3-aryl-2-cyanol-1'-oxo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalene]-2-carboxamides as a single diastereoisomer. The stereoconfiguration of the products was determined by H-1 and C-13 NMR spectroscopy.