(S)-2-cyclohexyl-3,3,3-trifluoropropyl 2-naphthoate | 1373038-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-cyclohexyl-3,3,3-trifluoropropyl 2-naphthoate
• CAS: 1373038-23-3
• 化学式: C₂₀H₂₁F₃O₂
• 分子量: 350.381
• InChiKey: JERGDALHMOMNHH-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  环己基乙醛 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 Ir(ppy)2(dtb-bpy)PF₆ 、 (2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one trifluoroacetate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (S)-2-cyclohexyl-3,3,3-trifluoropropyl 2-naphthoate
  参考文献：
  名称：

  Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

  摘要：

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

  DOI：

  10.1021/ja9053338

文献信息

• A Simple Method for Asymmetric Trifluoromethylation of <i>N</i>-Acyl Oxazolidinones via Ru-Catalyzed Radical Addition to Zirconium Enolates
  作者：Aaron T. Herrmann、Lindsay L. Smith、Armen Zakarian

  DOI：10.1021/ja302552e

  日期：2012.4.25

  good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.

  已经开发了 Ru 催化的 N-酰基恶唑烷酮的直接热三氟甲基化和全氟烷基化。该反应在实验上很简单，需要廉价的试剂，同时提供良好的立体控制水平的产品收率。初步研究表明，与官能团、芳烃和某些杂芳烃取代基具有显着的相容性。所描述的方法为以实验方便的方式合成氟化材料提供了一种有用的替代方法。
• The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes
  作者：Anna E. Allen、David W. C. MacMillan

  DOI：10.1021/ja100748y

  日期：2010.4.14

  An enantioselective organocatalytic alpha-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched alpha-trifluoromethylated aldehydes through a nonphotolytic pathway.