c-hexyl trifluorothioacetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: c-hexyl trifluorothioacetate
• 英文别名: S-cyclohexyl 2,2,2-trifluoroethanethioate
• 化学式: C₈H₁₁F₃OS
• 分子量: 212.236
• InChiKey: CFTLQJJWWNLJHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  c-hexyl trifluorothioacetate 、 苯硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 噻吩-2-甲酸亚铜(I) 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 为溶剂， 以26%的产率得到2,2,2-三氟苯乙酮
  参考文献：
  名称：

  Palladium-catalyzed fluoroacylation of (Hetero)arylboronic acid with fluorothioacetates at ambient temperature

  摘要：

  A palladium-catalyzed fluoroacylation of (hetero)aryl boronic acid with the fluorothioacetates is described at ambient temperature. A variety of aryl, and heteroaryl boronic acids are compatible in the reaction, affording the corresponding fluoroalkyl ketones in moderate to good yields. Further late-stage di-, and trifluoroacylation of drug molecule clofibrate and estrone demonstrated the synthetic practicability of this protocol.2009 Elsevier Ltd. All rights reserved. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151780
• 作为产物：
  描述：

  环己硫醇 、 三氟乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到c-hexyl trifluorothioacetate
  参考文献：
  名称：

  Synthetic Uses of Thio- and Selenoesters of Trifluoromethylated Acids. 1. Preparation of Trifluoromethyl Sulfides and Selenides

  摘要：

  Trifluorothioacetates (CF3CO-S-R, from (CF3CO)(2)O and thiols) as well as trifluoromethanethio-or trifluoromethaneselenosulfonates (CF3SO2-Y-R; Y = S, Se; from CF3SO2Na, RYYR, and Br-2) can be formally decarbonylated or desulfonylated, respectively, provided that they are photolyzed at 40 degrees C in the presence of 1 equiv of the corresponding disulfide or diselenide. Trifluoromethyl sulfides or selenides are obtained, and the added disulfide (or diselenide) is recovered after reaction. In such a way, S-(trifluoromethyl)cysteine derivatives can be obtained.

  DOI：

  10.1021/jo980649a