1-(3-chlorophenyl)-2-((trifluoromethyl)thio)propan-1-one | 1612226-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-chlorophenyl)-2-((trifluoromethyl)thio)propan-1-one
• 英文别名: 1-(3-Chlorophenyl)-2-(trifluoromethylsulfanyl)propan-1-one
• CAS: 1612226-20-6
• 化学式: C₁₀H₈ClF₃OS
• 分子量: 268.687
• InChiKey: RZPAOVIUZJYYES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-溴-3'-氯苯丙酮 、 (三氟甲基)三甲基硅烷 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 potassium fluoride 、 1,10-菲罗啉 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以64%的产率得到1-(3-chlorophenyl)-2-((trifluoromethyl)thio)propan-1-one
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of α-Trifluoromethylthio-Substituted Ketones

  摘要：

  The CF3S-substituted moiety serves as an important structural element in many bioactive molecules. A versatile copper catalyst that allowed for trifluoromethylthiolation of primary and secondary α-bromoketones is described. The reaction with readily available elemental sulfur and CF3SiMe3 afforded a broad scope and moderate to good yields of α-trifluoromethylthio-substituted ketones. This procedure represents a very operationally simple yet powerful strategy for the synthesis of α-trifluoromethylthio-substituted ketones, a useful and versatile class of synthetic synthons.

  DOI：

  10.1021/ol501290p

文献信息

• An Improved Protocol for the Synthesis of α-Trifluoromethylthio-Substituted Ketones by Copper-Mediated Trifluoromethylthiolation of α-Bromo Ketones
  作者：Yangjie Huang、Xing He、Haohong Li、Zhiqiang Weng

  DOI：10.1002/ejoc.201403221

  日期：2014.11

  An efficient and practical approach to α-trifluoromethylthio-substituted ketones was developed. The trifluoromethylthiolation of (bpy)Cu(SCF3) (bpy = 2,2′-bipyridyl) with various α-bromo ketones afforded the desired α-trifluoromethylthio-substituted ketones in good yields. The reaction tolerates more functionally than previously reported methods and demonstrates efficient scalability and practicality

  开发了一种有效且实用的 α-三氟甲硫基取代酮方法。(bpy)Cu(SCF3)（bpy = 2,2'-联吡啶）与各种 α-溴酮的三氟甲硫基化以良好的产率提供了所需的 α-三氟甲硫基取代的酮。该反应比以前报道的方法在功能上具有更多的耐受性，并证明了有效的可扩展性和实用性。
• An Unconventional Mechanistic Insight into SCF₃Formation from Difluorocarbene: Preparation of¹⁸F-Labeled α-SCF₃Carbonyl Compounds
  作者：Jian Zheng、Ran Cheng、Jin-Hong Lin、Dong-Hai Yu、Longle Ma、Lina Jia、Lan Zhang、Lu Wang、Ji-Chang Xiao、Steven H. Liang

  DOI：10.1002/anie.201611761

  日期：2017.3.13

  trifluoromethyl anion‐based theory. Mechanistic elucidation reveals an unprecedented chemical process for the formation of thiocarbonyl fluoride and also enables transition‐metal‐mediated trifluoromethylthiolation and [18F]trifluoromethylthiolation of α‐bromo carbonyl compounds with broad substrate scope and compatibility.

  首次描述了通过用元素硫将二氟卡宾硫化来进行三氟甲基硫醇化反应，该方法取代了长期以来基于三氟甲基阴离子的理论。机理的揭示揭示了形成硫代羰基氟化物的空前的化学过程，还使过渡金属介导的α-溴代羰基化合物的三氟甲基硫醇化和[ 18 F]三氟甲基硫代化具有广泛的底物范围和相容性。