(E)-N-benzyl-2-cyano-3-(4-bromophenyl)acrylamide

• 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-(4-bromophenyl)acrylamide
• 英文别名: N-benzyl-3-(4-bromophenyl)-2-cyanoacrylamide；(E)-N-benzyl-3-(4-bromophenyl)-2-cyano-2-propenamide；(E)-N-benzyl-3-(4-bromophenyl)-2-cyanoprop-2-enamide
• 化学式: C₁₇H₁₃BrN₂O
• 分子量: 341.207
• InChiKey: GIDBUZGWLNIYCF-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 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-(4-bromophenyl)acrylamide 、 二溴丙二酸二乙酯 在 锌 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以69%的产率得到3-benzyl-6-(4-bromophenyl)-5-cyano-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
• 作为产物：
  描述：

  2-氰基-N-(苯基甲基)-乙酰胺 、 对溴苯甲醛 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 生成 (E)-N-benzyl-2-cyano-3-(4-bromophenyl)acrylamide
  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

• Organocatalytic cascade reactions: diversity-oriented synthesis for the construction of hydroisoquinoline scaffolds
  作者：Clarisa Villegas Gómez、David Cruz Cruz、Rasmus Mose、Karl Anker Jørgensen

  DOI：10.1039/c4cc01231c

  日期：——

  highly functionalized hydroisoquinolines by trienamine-mediated [4+2]-cycloaddition/nucleophilic ring-closing reaction cascade sequence of cyanoacrylamides with 2,4-dienals is presented. The corresponding cycloadducts are formed in high yields and excellent stereoselectivities. Moreover, a series of transformations demonstrate the synthetic application of the obtained hydroisoquinolines.

  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。
• 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.
• Synthesis of 3-substituted ethyl esters of 6-aryl-5-cyano-2,4-dioxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid, based on a modified reformatsky reaction
  作者：V. V. Shchepin、P. S. Silaychev

  DOI：10.1007/s10593-006-0038-x

  日期：2005.12
• 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.