(Z)-N-(2-(5-methoxybenzofuran-3-yl)-1-(thiophen-2-yl)vinyl)-N-phenylacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-N-(2-(5-methoxybenzofuran-3-yl)-1-(thiophen-2-yl)vinyl)-N-phenylacetamide
• 英文别名: N-[(Z)-2-(5-methoxy-1-benzofuran-3-yl)-1-thiophen-2-ylethenyl]-N-phenylacetamide
• 化学式: C₂₃H₁₉NO₃S
• 分子量: 389.475
• InChiKey: FIMXPYPRDDFCPZ-BKUYFWCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰溴 、 以 二氯甲烷 为溶剂， 反应 8.0h， 以85%的产率得到(Z)-N-(2-(5-methoxybenzofuran-3-yl)-1-(thiophen-2-yl)vinyl)-N-phenylacetamide
  参考文献：
  名称：

  从酰基亚胺/酰胺基烯丙基到高度官能化的丙二烯中间体：Z-酰胺基呋喃，-吡咯，-噻吩，-苯并呋喃和-苯并噻吩的立体选择性制备

  摘要：

  AbstractThis paper describes the development of a facile protocol to a highly functionalized amidoallenylium by treatment of alkynylimine with acyl bromide in dichloromethane, which may give tetrasubstituted allene intermediates and yield furans, pyrroles, thiophenes, benzofurans and benzothiophenes. The plausible mechanism was discussed and a reaction intermediate was isolated. With the stereoselective transformation of the tetrasubstituted allene intermediate and efficient conversion to versatile heterocyclic compounds, this protocol will be useful to the organic and medicinal chemistry community.magnified image

  DOI：

  10.1002/adsc.201400713

文献信息

• From Acyliminiums/Amidoallenyliums to Highly Functionalized Allene Intermediates: Stereoselective Preparation of<i>Z</i>-Amidovinyl-Furans, -Pyrroles, -Thiophenes, -Benzofurans and -Benzothiophenes
  作者：Le Liu、Dianpeng Chen、Hongwei Zhou

  DOI：10.1002/adsc.201400713

  日期：2015.2.9

  AbstractThis paper describes the development of a facile protocol to a highly functionalized amidoallenylium by treatment of alkynylimine with acyl bromide in dichloromethane, which may give tetrasubstituted allene intermediates and yield furans, pyrroles, thiophenes, benzofurans and benzothiophenes. The plausible mechanism was discussed and a reaction intermediate was isolated. With the stereoselective transformation of the tetrasubstituted allene intermediate and efficient conversion to versatile heterocyclic compounds, this protocol will be useful to the organic and medicinal chemistry community.magnified image