1-(trifluoromethylthio)hexadecan-2-one | 1612226-17-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 1-(trifluoromethylthio)hexadecan-2-one
• 英文别名: 1-(Trifluoromethylsulfanyl)hexadecan-2-one
• CAS: 1612226-17-1
• 化学式: C₁₇H₃₁F₃OS
• 分子量: 340.494
• InChiKey: BWVKCDLIIAQJDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-2-六癸酮 、 (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85%的产率得到1-(trifluoromethylthio)hexadecan-2-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。