(Z)-N,N-diethyl-4-fluoro-2-(trifluoromethyl)icos-4-enamide | 1415414-41-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-N,N-diethyl-4-fluoro-2-(trifluoromethyl)icos-4-enamide
• CAS: 1415414-41-3
• 化学式: C₂₅H₄₅F₄NO
• 分子量: 451.632
• InChiKey: SYQBOAKYJOZJSZ-XDOYNYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.76
• 重原子数：
  31.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-fluorooctadec-1-en-3-ol 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以72%的产率得到(Z)-N,N-diethyl-4-fluoro-2-(trifluoromethyl)icos-4-enamide
  参考文献：
  名称：

  Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols

  摘要：

  A new, mild method to prepare alpha-trifluoromethylated amides bearing an additional trans-configured double bond in gamma-position is described. Treatment at room temperature of fluorinated and non-fluorinated allylic alcohols 1 and 2 with the 1,1,3,3,3-pentafluoropropene-diethylamine adduct (PFPDEA) in the presence of triethylamine as base gave the products of [3,3]-sigmatropic Eschenmoser-Claisen-type rearrangements with good yields and excellent diastereoselectivity due to chair-like conformations of transition states. Starting with enantiomerically enriched allylic alcohols chirality transfer from carbon 3 of the allylic system to carbon 2 of the final alpha-trifluoromethyl carboxamides was observed. This methodology was applied to both simple and more complex, including terpenic, allylic alcohols and might be developed to an alternative strategy to the well-known electrophilic alpha-trifluoromethylation of carbonyl compounds. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.07.011