(6E)-3-fluoro-3,7,11-trimethyldodeca-1,6,10-triene | 1422173-24-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (6E)-3-fluoro-3,7,11-trimethyldodeca-1,6,10-triene
• CAS: 1422173-24-7
• 化学式: C₁₅H₂₅F
• 分子量: 224.362
• InChiKey: ZVYDBALJQLKBDG-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol 在 potassium fluoride 、 1,3-双(2,6-二异丙苯基)-2,2-二氟-2,3-二氢-1H-咪唑 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以53%的产率得到(6E)-3-fluoro-3,7,11-trimethyldodeca-1,6,10-triene
  参考文献：
  名称：

  Late-Stage Deoxyfluorination of Alcohols with PhenoFluor

  摘要：

  An operationally simple protocol for the selective deoxyfluorination of structurally complex alcohols is presented. Several fluorinated derivatives of natural products and pharmaceuticals have been prepared to showcase the potential of the method for late-stage diversification and its functional group compatibility. A series of simple guidelines for predicting the selectivity in substrates with multiple alcohols is given.

  DOI：

  10.1021/ja3125405

文献信息

• Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols
  作者：Justyna Walkowiak、Magdalena Tomas-Szwaczyk、Günter Haufe、Henryk Koroniak

  DOI：10.1016/j.jfluchem.2012.07.011

  日期：2012.11

  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.