isobutyl 2-cyano-3-phenylacrylate | 184765-38-6

• 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: isobutyl 2-cyano-3-phenylacrylate
• 英文别名: 2-Methylpropyl 2-cyano-3-phenylprop-2-enoate
• CAS: 184765-38-6
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: HDLAXWUPDSJCLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±30.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异丁醇 、 α-氰基肉桂酸 在 硫酸 、 乙腈 作用下， 反应 18.0h， 以85%的产率得到isobutyl 2-cyano-3-phenylacrylate
  参考文献：
  名称：

  One-Pot Esterification and Amide Formation via Acid-Catalyzed Dehydration and Ritter Reactions

  摘要：

  Esterification of carboxylic acid is achieved using acetonitrile as a water trap. Water liberated during esterification is consumed in cyanide hydrolysis, thereby driving the esterification to completion. Substrates having carboxylic acid and nitrile groups undergo intramolecular dehydration and rehydration to amido esters in the absence of acetonitrile. Cyano acids also undergo esterification and Ritter reaction in one pot when excess alcohol is used. For the first time, we have observed an interesting Ritter reaction of primary alcohols, leading to ester amide product in one pot. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.837485

文献信息

• One-Pot Esterification and Amide Formation via Acid-Catalyzed Dehydration and Ritter Reactions
  作者：Pankaj Dawar、M. Bagavan Raju、Ramesha Andagar Ramakrishna

  DOI：10.1080/00397911.2013.837485

  日期：2014.3.19

  Esterification of carboxylic acid is achieved using acetonitrile as a water trap. Water liberated during esterification is consumed in cyanide hydrolysis, thereby driving the esterification to completion. Substrates having carboxylic acid and nitrile groups undergo intramolecular dehydration and rehydration to amido esters in the absence of acetonitrile. Cyano acids also undergo esterification and Ritter reaction in one pot when excess alcohol is used. For the first time, we have observed an interesting Ritter reaction of primary alcohols, leading to ester amide product in one pot. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]