(Z)-3-(butylamino)-3-oxo-1-phenylprop-1-en-2-yl 2-phenylacetate | 1187670-23-0

• 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: (Z)-3-(butylamino)-3-oxo-1-phenylprop-1-en-2-yl 2-phenylacetate
• 英文别名: (Z)-1-(n-butylcarbamoyl)-2-phenylvinyl 2-phenylacetate；[(Z)-3-(butylamino)-3-oxo-1-phenylprop-1-en-2-yl] 2-phenylacetate
• CAS: 1187670-23-0
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: SVLVBQPDZHOZBN-CYVLTUHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-(butylamino)-3-oxo-1-phenylprop-1-en-2-yl 2-phenylacetate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 0.5h， 以60%的产率得到3-benzyl-1-butyl-3-hydroxy-4-phenylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Isocyanides and Arylacetic Acids: Synthesis and Reactivity of 3-Aryl-2-acyloxyacrylamides, an Example of Serendipity-Oriented Synthesis

  摘要：

  Research progress is often promoted by unexpected results that open the way to new scenarios. In this communication, an unprecedented condensation of arylacetic acids and isocyanides and the unusual base-mediated rearrangement of the resulting products to give two novel classes of polysubstituted pyrrolones and pyrrolidinediones are reported.

  DOI：

  10.1021/ol901512c
• 作为产物：
  描述：

  苯乙酸 、 异腈基正丁烷 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到(Z)-3-(butylamino)-3-oxo-1-phenylprop-1-en-2-yl 2-phenylacetate
  参考文献：
  名称：

  Isocyanides and Arylacetic Acids: Synthesis and Reactivity of 3-Aryl-2-acyloxyacrylamides, an Example of Serendipity-Oriented Synthesis

  摘要：

  Research progress is often promoted by unexpected results that open the way to new scenarios. In this communication, an unprecedented condensation of arylacetic acids and isocyanides and the unusual base-mediated rearrangement of the resulting products to give two novel classes of polysubstituted pyrrolones and pyrrolidinediones are reported.

  DOI：

  10.1021/ol901512c

文献信息

• On the reaction of carboxylic acids and isonitriles with conventional heating
  作者：Jason G. Polisar、Jack R. Norton

  DOI：10.1016/j.tet.2012.09.068

  日期：2012.12

  Control over the formation of N-formylamides versus the formation of captodative alkenes from the reaction of arylacetic acids with isonitriles has been achieved. Low temperatures and high concentrations favor alkenes, and high temperatures and low concentrations favor N-formylamides. (c) 2012 Elsevier Ltd. All rights reserved.
• Isocyanides and Arylacetic Acids: Synthesis and Reactivity of 3-Aryl-2-acyloxyacrylamides, an Example of Serendipity-Oriented Synthesis
  作者：Andrea Basso、Luca Banfi、Andrea Galatini、Giuseppe Guanti、Federico Rastrelli、Renata Riva

  DOI：10.1021/ol901512c

  日期：2009.9.17

  Research progress is often promoted by unexpected results that open the way to new scenarios. In this communication, an unprecedented condensation of arylacetic acids and isocyanides and the unusual base-mediated rearrangement of the resulting products to give two novel classes of polysubstituted pyrrolones and pyrrolidinediones are reported.