phenyl(2,2,2-trifluoro-1-phenylethyl)sulfane | 123228-00-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl(2,2,2-trifluoro-1-phenylethyl)sulfane
• 英文别名: Benzene, [(2,2,2-trifluoro-1-phenylethyl)thio]-；(2,2,2-trifluoro-1-phenylethyl)sulfanylbenzene
• CAS: 123228-00-2
• 化学式: C₁₄H₁₁F₃S
• 分子量: 268.303
• InChiKey: YCHPFOXGVGKIJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl(2,2,2-trifluoro-1-phenylethyl)sulfane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 间氯过氧苯甲酸 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1,1,1-trifluoro-2-phenylpent-4-en-2-ylsulfonyl)benzene
  参考文献：
  名称：

  Decarboxylative Allylation of Trifluoroethyl Sulfones and Approach to Difluoromethyl Compounds

  摘要：

  Ally, carbonates undergo palladium-catalyzed decarboxylative allylation of trifluoroethyl phenyl sulfones. The success of the allylation, which is not efficient under typical strong base-mediated conditions, is the result of mild conditions thanks to a progressive delivery of ethoxide. Indeed, ethyl allyl carbonates act as a latent source of ethoxide for generation of the trifluoroethyl carbanion that reacts with the pi-allylpalladium complex. The utility of the method is illustrated in a new approach to difluoromethyl compounds.

  DOI：

  10.1021/ol302589w
• 作为产物：
  描述：

  2,2,2-trifluoroethyl phenyl sulfide 在 磺酰氯 、 zinc(II) chloride 作用下， 以 硝基甲烷 、 正己烷 为溶剂， 反应 0.5h， 生成 phenyl(2,2,2-trifluoro-1-phenylethyl)sulfane
  参考文献：
  名称：

  2,2,2-三氟-1-苯基亚磺酰基乙基碳正离子的产生和反应

  摘要：

  路易斯酸催化的1-氯-2,2,2-三氟乙基苯硫醚的脱氯反应生成2,2,2-三氟-1-苯基亚磺酰基乙基碳正离子，它与芳族化合物发生亲电反应。

  DOI：

  10.1016/s0040-4039(00)99666-7

文献信息

• Copper-Catalyzed Insertion into Heteroatom-Hydrogen Bonds with Trifluorodiazoalkanes
  作者：Stephen Hyde、Janis Veliks、Benoît Liégault、David Grassi、Marc Taillefer、Véronique Gouverneur

  DOI：10.1002/anie.201511954

  日期：2016.3.7

  Copper‐catalyzed Si−H, B−H, P−H, S−H, and N−H insertion reactions of 2,2,2‐trifluoro‐1‐diazoethane and 1‐aryl 2,2,2‐trifluorodiazoethanes generated a large number of new fluorine‐containing chemical entities for medicinal chemists. With selected Si−H and B−H insertion reactions, we demonstrate successful extension to asymmetric catalysis.

  铜催化的2,2,2-三氟-1-重氮乙烷和1-芳基2,2,2-三氟重氮乙烷的Si-H，B-H，P-H，S-H和N-H插入反应产生了大量用于药物化学家的新的含氟化学实体。通过选择的Si-H和B-H插入反应，我们证明了不对称催化的成功延伸。
• Functional group transformation of α-trifluoromethylated alcohol derivatives
  作者：Toshiki Hagiwara、Katsumi Tanaka、Takamasa Fuchikami

  DOI：10.1016/0040-4039(96)01857-6

  日期：1996.11

  Functional group transformation of α-trifluoromethylated alcohols was investigated. Nucleophilic substitutions of their sulfonates was achieved in the presence of metal fluoride as a base with complete inversion of the configuration.

  研究了α-三氟甲基化醇的官能团转化。它们的磺酸盐的亲核取代是在金属氟化物作为碱的存在下实现的，该构型完全反转。
• Efficient synthesis of novel α-aryl(alkyl)-β, β-difluorovinyl and α-aryl(alkyl)-β-fluoro-β-perfluoroalkylvinyl sulfides
  作者：In Howa Jeong、Yong Ki Min、Young Sup Kim、Bum Tae Kim、Kwang Yun Cho

  DOI：10.1016/0040-4039(94)80117-7

  日期：1994.10

  1-vis(phenylthio)perfluoroalkyl aromatics or alkanes with a mixture of 2 equiv. of TiCl4 and 4 equiv. of LiAlH4 in THF at reflux temperature for 3 hours afforded α-aryl(alkyl)-β-fluoro-β-perfluoroalkylvinyl and α-aryl (alkyl)-β-fluoro-β-perfluoroalkylvinyl sulfides in good yields.

  1,1-对（苯硫基）全氟烷基芳烃或烷烃与2当量混合物的反应 TiCl 4和4当量的 将LiAlH 4在THF中在回流温度下反应3小时，以良好的收率得到α-芳基（烷基）-β-氟-β-全氟烷基乙烯基硫化物和α-芳基（烷基）-β-氟-β-全氟烷基乙烯基硫化物。
• TFA‐Promoted Intermolecular Friedel‐Crafts Alkylation of Arenes with 2,2,2‐Trifluoroethylaryl Sulfoxides
  作者：Zhen Deng、Liu‐Yan Qiu、Wenjie Pan、Baiyu Qian、Jie Chen、Hui Zhang、Qing‐Yun Chen、Weiguo Cao、Xiao‐Jun Tang

  DOI：10.1002/asia.202200190

  日期：2022.7.15

  corresponding 2,2,2-trifluoroethylaryl sulfoxide. When using TFA.as the solvent at elevated temperature, this analogue of trifluoroethyl carbocation can be restored from S,O-acetal to achieve Friedel-Crafts alkylation of arenes.

  α-CF 3 thionium是相应的 2,2,2-三氟乙基芳基亚砜的 Pummerer 重排反应中间体。当在高温下使用TFA.作为溶剂时，这种三氟乙基碳正离子类似物可以从S，O-缩醛中还原，从而实现芳烃的Friedel-Crafts烷基化。
• Electrolytic reactions of fluoro organic compounds. 7. Anodic methoxylation and acetoxylation of 2,2,2-trifluoroethyl sulfides. Preparation of highly useful trifluoromethylated building blocks
  作者：Toshio Fuchigami、Kayoko Yamamoto、Yuki Nakagawa

  DOI：10.1021/jo00001a028

  日期：1991.1

  Anodic methoxylation and acetoxylation of 2,2,2-trifluoroethyl sulfides and the corresponding nonfluorinated sulfides were comparatively studied. It was found that a trifluoromethyl group remarkably promoted anodic substitution and methoxy and acetoxy groups were introduced adjacent to the trifluoromethyl group of the sulfides. Longer perfluoroalkyl groups also promoted these anodic substitutions. These products were shown to be highly useful building blocks for the synthesis of fluoro organic compounds.