(E)-3,7-dimethyl-1-(trifluoromethoxy)octa-2,6-diene | 1241960-14-4

• 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: (E)-3,7-dimethyl-1-(trifluoromethoxy)octa-2,6-diene
• 英文别名: (6E)-2,6-dimethyl-8-(trifluoromethoxy)octa-2,6-diene；(2E)-3,7-dimethyl-1-(trifluoromethoxy)octa-2,6-diene
• CAS: 1241960-14-4
• 化学式: C₁₁H₁₇F₃O
• 分子量: 222.251
• InChiKey: DBIFRFTYXWQUFL-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三氟甲烷磺酸三氟甲酯 、 1-碘-3,7-二甲基辛-2,6-二烯 在 四丁基氟化铵 作用下， 反应 2.0h， 生成 (E)-3,7-dimethyl-1-(trifluoromethoxy)octa-2,6-diene
  参考文献：
  名称：

  A deeper insight into direct trifluoromethoxylation with trifluoromethyl triflate

  摘要：

  Commercially available fluorides (silver fluoride and n-tetrabutylammonium triphenyldifluorosilicate), combined with TFMT, allow a simple generation, in situ, of silver and n-tetrabutylammonium trifluoromethoxides which were able to react with electrophilic substrates. Silver trifluoromethoxide, which is usually more efficient than n-tetrabutylammonium trifluoromethoxide, converts, under mild conditions, primary aliphatic bromides and iodides, as well as primary and secondary benzylic or allylic bromides to the corresponding trifluoromethoxylated compounds. Several trifluoromethyl ethers, which could be valuable building-blocks, were prepared in such a way. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.11.006

文献信息

• Study of a Stable “Trifluoromethoxide Anion Solution” Arising from 2,4‐Dinitro‐Trifluoromethoxybenzene
  作者：Clémence Bonnefoy、Emmanuel Chefdeville、Armen Panosian、Gilles Hanquet、Frédéric R. Leroux、Fabien Toulgoat、Thierry Billard

  DOI：10.1002/chem.202102809

  日期：2021.11.17

  A stable solution of the trifluoromethoxide anion was readily obtained by mixing 2,4-dinitro-trifluoromethoxybenzene (DNTFB) and DMAP. A detailed study and characterization of this solution has been described, in particular highlighting the crucial role of the DNTFB/DMAP ratio. This “trifluoromethoxide anion solution” was applied to perform metal-free SN2 reactions on alkyl bomides with yields up to

  通过混合 2,4-二硝基-三氟甲氧基苯 (DNTFB) 和 DMAP，很容易获得三氟甲氧基阴离子的稳定溶液。该解决方案的详细研究和表征已被描述，特别强调了 DNTFB/DMAP 比率的关键作用。这种“三氟甲氧基阴离子溶液”用于对烷基硼化物进行无金属的 S N 2 反应，产率高达 77%。
• Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers
  作者：Jian-Bo Liu、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1021/acs.orglett.5b02522

  日期：2015.10.16

  The development of an efficient and practical method for the preparation of alkyl trifluoromethyl ethers is urgently demanding. The silver-mediated oxidative O-trifluoromethylation of primary, secondary, and tertiary alcohols with TMSCF3 under mild reaction conditions is established to provide a novel approach to a broad range of alkyl trifluoromethyl ethers. Further, this method is applied to the late-stage O-trifluoromethylation of complex natural products and prescribed pharmaceutical agents.