trans-1-Phenyl-2-(difluoromethyl)-4-(p-tolyl)-1,2,3,4-tetrahydroquinoline | 128644-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: trans-1-Phenyl-2-(difluoromethyl)-4-(p-tolyl)-1,2,3,4-tetrahydroquinoline
• CAS: 128644-92-8；137608-03-8
• 化学式: C₂₃H₂₁F₂N
• 分子量: 349.423
• InChiKey: IVZSJJQEPCQPMU-UNMCSNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  N-(2,2-Difluoroethyl)-N,N-diphenylamine 在 氢氧化钾 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 trans-1-Phenyl-2-(difluoromethyl)-4-(p-tolyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks

  摘要：

  Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH(2)R(f) (R(f) = CF3, CHF2, CH2F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position a to the fluoromethyl (R(f)) group, depending on the R(f) and R groups. The effect of the R(f) group on the promotion of the anodic alpha-methoxylation decreased in the order CF3, CHF2, and CH2F. This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the alpha-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines. The alpha-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds alpha to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods.

  DOI：

  10.1021/jo00082a018

文献信息

• Cationic Polar Cycloaddition with Anodically Prepared a-Tri- and a-Difluoromethylated N,O-Acetals: Preparation of Fluoromethylated Tetra- and Dihydroquinoline Derivatives
  作者：Toshio Fuchigami、Shinji Ichikawa、Zaghloul e. Kandeel、Akinori Konno、Tsutomu Nonaka

  DOI：10.3987/com-89-5295

  日期：——