3-dibenzothiophen-4-yl-N,N-dimethyl-4-thiophen-2-ylpent-4-enamide | 1118669-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-dibenzothiophen-4-yl-N,N-dimethyl-4-thiophen-2-ylpent-4-enamide
• CAS: 1118669-30-9
• 化学式: C₂₃H₂₁NOS₂
• 分子量: 391.558
• InChiKey: SADQNRMAPASMBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,1-二甲氧基-N,N-二甲基乙胺 、 3-dibenzothiophen-4-yl-2-thiophen-2-ylprop-2-en-1-ol 在 四丁基氟化铵 作用下， 以 水 、 甲苯 为溶剂， 反应 3.0h， 以95%的产率得到3-dibenzothiophen-4-yl-N,N-dimethyl-4-thiophen-2-ylpent-4-enamide
  参考文献：
  名称：

  Tetra-n-butylammonium Fluoride–Catalyzed Eschenmoser–Claisen [3,3]-Sigmatropic Rearrangement

  摘要：

  Condensation of dibenzofuran and dibenzothiophene carboxaldehydes with various aryl acetic acids followed by esterification of the acid intermediate afforded the 2,3-diaryl acrylates in good overall yields. Reduction of the esters with diisobutylaluminium hydride afforded the allylic alcohols, which underwent a smooth Eschenmoser-Claisen [3,3]-sigmatropic rearrangement on exposure to N,N-dimethylacetamide dimethylacetal in the presence of tetra n-butylammonium fluoride as catalyst to give 3,4-diaryl ,-unstaturated amides in excellent yields.

  DOI：

  10.1080/00397910802374075

文献信息

• Tetra-<i>n</i>-butylammonium Fluoride–Catalyzed Eschenmoser–Claisen [3,3]-Sigmatropic Rearrangement
  作者：V. S. Prasada Rao Lingam、Ramanatham Vinodkumar、Khagga Mukkanti、Abraham Thomas、Balasubramanian Gopalan

  DOI：10.1080/00397910802374075

  日期：2008.12.31

  Condensation of dibenzofuran and dibenzothiophene carboxaldehydes with various aryl acetic acids followed by esterification of the acid intermediate afforded the 2,3-diaryl acrylates in good overall yields. Reduction of the esters with diisobutylaluminium hydride afforded the allylic alcohols, which underwent a smooth Eschenmoser-Claisen [3,3]-sigmatropic rearrangement on exposure to N,N-dimethylacetamide dimethylacetal in the presence of tetra n-butylammonium fluoride as catalyst to give 3,4-diaryl ,-unstaturated amides in excellent yields.