3-dibenzofuran-4-yl-N,N-dimethyl-4-(4-phenylphenyl)pent-4-enamide | 1118669-15-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-dibenzofuran-4-yl-N,N-dimethyl-4-(4-phenylphenyl)pent-4-enamide
• CAS: 1118669-15-0
• 化学式: C₃₁H₂₇NO₂
• 分子量: 445.561
• InChiKey: VWPBCSYEYSMBEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  631.7±55.0 °C(predicted)
• 密度：
  1.162±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,1-二甲氧基-N,N-二甲基乙胺 、 3-dibenzofuran-4-yl-2-(4-phenylphenyl)prop-2-en-1-ol 在 四丁基氟化铵 作用下， 以 水 、 甲苯 为溶剂， 反应 5.0h， 以91%的产率得到3-dibenzofuran-4-yl-N,N-dimethyl-4-(4-phenylphenyl)pent-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.