2'-(2,2,2-trifluoroethyl)acetophenone | 1393558-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(2,2,2-trifluoroethyl)acetophenone
• 英文别名: 1-(2-(2,2,2-trifluoroethyl)phenyl)ethanone；1-[2-(2,2,2-Trifluoroethyl)phenyl]ethanone；1-[2-(2,2,2-trifluoroethyl)phenyl]ethanone
• CAS: 1393558-72-9
• 化学式: C₁₀H₉F₃O
• 分子量: 202.176
• InChiKey: PUTHJMAHMYZVJN-UHFFFAOYSA-N

物化性质

• 沸点：
  217.9±40.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2,2’-bipyridine)Zn(CF₃)₂ 、 苯丙酮 在 copper(II) bis(trifluoromethanesulfonate) 、 1-methyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 以74%的产率得到2'-(2,2,2-trifluoroethyl)acetophenone
  参考文献：
  名称：

  铜催化后期苯甲酰C（sp 3）–H三氟甲基化

  摘要：

  C（sp 3）–H键的直接三氟甲基化，尤其是在后期阶段，仍然是一个艰巨的挑战。在这里，我们描述了铜催化的苄基C（sp 3）–H三氟甲基化。以Cu（I）或Cu（II）为催化剂，以（bpy）Zn（CF 3）2（bpy = 2,2'-联吡啶）作为CF 3源，以NFSI（或Selectfluor）作为氧化剂选择性苄基C（sp 3）–H三氟甲基化已在温和条件下成功高效地实施。该协议不仅展示了广泛的底物范围和广泛的官能团兼容性，而且还允许对天然产物或药物衍生物进行有效的后期C（sp 3）–H三氟甲基化。

  DOI：

  10.1016/j.chempr.2019.02.006

文献信息

• Benzylic C–H Trifluoromethylation via Photoenol
  作者：Takafumi Ide、Shuya Masuda、Yuji Kawato、Hiromichi Egami、Yoshitaka Hamashima

  DOI：10.1021/acs.orglett.7b01971

  日期：2017.9.1

  Photoenols generated in situ from ortho-methyl-substituted phenylketones such as benzophenones and acetophenones were trifluoromethylated with Togni reagent without any additive or catalyst. This trifluoromethylation reaction proceeded smoothly under photoirradiation conditions (365 nm). Various functional groups were tolerant of the reaction conditions. Interestingly, the trifluoromethyl group was exclusively introduced at the ortho-benzylic position. Mechanistic studies suggested that this reaction proceeds via formation of a photoenol, not via a radical pathway.
• 6,5-BICYCLIC OCTAHYDROPYRROLOPYRIDINE OREXIN RECEPTOR ANTAGONISTS
  申请人：Kim Ronald M.

  公开号：US20170320874A1

  公开（公告）日：2017-11-09

  The present invention is directed to 6,5-bicyclic octahydropyrrolopyridine compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
• Copper-Catalyzed Late-Stage Benzylic C(sp3)–H Trifluoromethylation
  作者：Haiwen Xiao、Zhonglin Liu、Haigen Shen、Benxiang Zhang、Lin Zhu、Chaozhong Li

  DOI：10.1016/j.chempr.2019.02.006

  日期：2019.4

  Direct trifluoromethylation of C(sp3)–H bonds, especially in late stages, remains a formidable challenge. Herein, we describe the copper-catalyzed benzylic C(sp3)–H trifluoromethylation. With Cu(I) or Cu(II) as the catalyst, (bpy)Zn(CF3)2 (bpy = 2,2′-bipyridine) as the CF3 source, and NFSI (or Selectfluor) as the oxidant, site-selective benzylic C(sp3)–H trifluoromethylation is successfully implemented

  C（sp 3）–H键的直接三氟甲基化，尤其是在后期阶段，仍然是一个艰巨的挑战。在这里，我们描述了铜催化的苄基C（sp 3）–H三氟甲基化。以Cu（I）或Cu（II）为催化剂，以（bpy）Zn（CF 3）2（bpy = 2,2'-联吡啶）作为CF 3源，以NFSI（或Selectfluor）作为氧化剂选择性苄基C（sp 3）–H三氟甲基化已在温和条件下成功高效地实施。该协议不仅展示了广泛的底物范围和广泛的官能团兼容性，而且还允许对天然产物或药物衍生物进行有效的后期C（sp 3）–H三氟甲基化。