N-vinyl-trans-cinnamide | 862658-25-1

• 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: N-vinyl-trans-cinnamide
• 英文别名: N-vinylcinnamyl amide；(E)-N-ethenyl-3-phenylprop-2-enamide
• CAS: 862658-25-1
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: BJRUUWFCRKQWOP-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-vinyl-trans-cinnamide 在 1,1'-双(二苯基膦)二茂铁 、 Wilkinson's catalyst 、 tris(dibenzylideneacetone)dipalladium (0) 氢气 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 1.0h， 生成 N-(1-naphthalen-2-ylethyl)-3-phenylpropionamide
  参考文献：
  名称：

  Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

  摘要：

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

  DOI：

  10.1021/jo050669u
• 作为产物：
  描述：

  碘化乙烯 、 反-肉桂酰胺 在 copper(l) iodide 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以50%的产率得到N-vinyl-trans-cinnamide
  参考文献：
  名称：

  Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

  摘要：

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

  DOI：

  10.1021/jo050669u

文献信息

• Vinylation of pyridylcarboxamides with vinyltrimethoxysilane
  作者：P. Arsenyan、A. Petrenko、S. Belyakov

  DOI：10.1007/s10593-012-0943-0

  日期：2012.3

  A convenient method has been developed for the direct N-vinylation of pyridylcarboxamides with vinyltrimethoxysilane in the presence of copper(II) acetate and tetrabutylammonium fluoride. The yield of N-vinylamides depends on the nature of the starting amide and the solvent. The molecular structure of the products was confirmed by X-ray structural analysis.
• VINYLAMINE CONTAINING COPOLYMER MICROPARTICLES AS ADDITIVES IN PAPERMAKING
  申请人：Hercules Incorporated

  公开号：EP2776481A1

  公开（公告）日：2014-09-17
• US8894816B2
  申请人：——

  公开号：US8894816B2

  公开（公告）日：2014-11-25
• [EN] VINYLAMINE CONTAINING COPOLYMER MICROPARTICLES AS ADDITIVES IN PAPERMAKING<br/>[FR] MICROPARTICULES DE COPOLYMÈRE CONTENANT UNE VINYLAMINE À TITRE D'ADDITIFS DANS LA FABRICATION DU PAPIER
  申请人：HERCULES INC

  公开号：WO2013070489A1

  公开（公告）日：2013-05-16

  Surfactant mediated, free radical initiated emulsion/dispersion polymerization of n-vinylformamide with styrene or substituted styrene copolymers, and its subsequently hydrolyzed products bearing formamide, amine and styrenic functionality are disclosed. Processes for polymerization, polymer composition, and hydrolysis of such polymers are also disclosed. These polymers bearing cationic functionality can be used in papermaking applications as dry strength additives, wet strength additives, retention aids, drainage aids, sizing agent, sizing promoter and pitch and stickies control agents.