1-(trifluoromethyl)ethenyl phenyl sulfide | 73194-33-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(trifluoromethyl)ethenyl phenyl sulfide
• 英文别名: α-(phenylthio)trifluoropropene；α-Phenylthiotrifluoropropene；2-phenylthio-1,1,1-trifluoropropene；2-phenylthio-3,3,3-trifluoropropene；3,3,3-trifluoroprop-1-en-2-ylsulfanylbenzene
• CAS: 73194-33-9
• 化学式: C₉H₇F₃S
• 分子量: 204.216
• InChiKey: XQPUZTFCOAKMKM-UHFFFAOYSA-N

物化性质

• 沸点：
  41-43 °C(Press: 0.5 Torr)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-(trifluoromethyl)ethenyl phenyl sulfide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到2-Trifluoromethyl-2-phenylsulfonyloxirane
  参考文献：
  名称：

  α- or β-trifluoromethyl epoxysulfones: New C3 reagents for heterocyclisation

  摘要：

  The syntheses of alpha- and beta-trifluoromethyl epoxysulfones 1 and 2 are described. Compound 1 reacts with nucleophiles and bis-nucleophiles to furnish trifluoromethyl ketones and triRuoromethyl heterocycles in good yield, while its isomer 2 leads to the opposite thiazole regioisomers with thioamides.

  DOI：

  10.1016/0022-1139(94)03212-i
• 作为产物：
  描述：

  苯次磺酰氯 在 氢氧化钾 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-(trifluoromethyl)ethenyl phenyl sulfide
  参考文献：
  名称：

  2-苯硫基3,3,3-三氟丙烯，其亚砜和砜：在1,3-偶极环加成中的合成和反应性

  摘要：

  3，3，3-三氟丙烯1的衍生物：α-硫化物2，亚砜3，砜4和溴化物6是有用的三氟甲基化合成子。与重氮化合物反应后，这些衍生物可以公平地以优异的收率得到三氟甲基取代的吡唑啉，吡唑，环丙烷或烯丙基砜。三氟丙烯衍生物2 – 4与N-苄基-偶氮甲亚胺叶立德的1,3-偶极环加成可提供双取代的3-三氟甲基-吡咯烷。

  DOI：

  10.1016/0040-4020(96)00082-8

文献信息

• 2-phenylthio-3,3,3-trifluoropropene, its sulfoxide or sulfone in Diels-Alder cycloadditions
  作者：Martine Redon、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/s0040-4020(97)00328-1

  日期：1997.5

  The Diels-Alder reaction of 2-phenylthio-3,3,3-trifluoropropene 1 and its derivatives sulfoxide 2 and sulfone 3, respectively was carried out with cyclopentadiene, 2,3-dimethylbutadiene, butadiene and isoprene to give the [4+2] cycloadducts in good to excellent yields. The particular reactivity of 2-phenylsulfinyl-3,3,3-trifluoropropene 2 is revealed as an α,β-isomerisation via cycloaddition, sulfenic

  分别与环戊二烯，2,3-二甲基丁二烯，丁二烯和异戊二烯进行2-苯基硫基3,3,3-三氟丙烯1及其衍生物亚砜2和砜3的Diels-Alder反应，得到[4 + 2 ]环加合物，收率好至极好。2-苯基亚磺酰基-3,3,3-三氟丙烯的特定反应性的2显露作为α，β异构化通过环加成，次磺酸消除readdition随后逆狄尔斯-阿尔德。
• Thiazolides as Novel Antiviral Agents. 2. Inhibition of Hepatitis C Virus Replication
  作者：Andrew V. Stachulski、Chandrakala Pidathala、Eleanor C. Row、Raman Sharma、Neil G. Berry、Alexandre S. Lawrenson、Shelley L. Moores、Mazhar Iqbal、Joanne Bentley、Sarah A. Allman、Geoffrey Edwards、Alison Helm、Jennifer Hellier、Brent E. Korba、J. Edward Semple、Jean-Francois Rossignol

  DOI：10.1021/jm201264t

  日期：2011.12.22

  We report the activities of a number of thiazolides [2-hydroxyaroyl-N-(thiazol-2-yl)amides] against hepatitis C virus (HCV) genotypes IA and IB, using replicon assays. The structure activity relationships (SARs) of thiazolides against HCV are less predictable than against hepatitis B virus (HBV), though an electron-withdrawing group at C(5') generally correlates with potency. Among the related salicyloylanilides, the m-fluorophenyl analogue was most promising; niclosamide and close analogues suffered from very low solubility and bioavailability. Nitazoxanide (NTZ) 1 has performed well in clinical trials against HCV. We show here that the 5'-Cl analogue 4 has closely comparable in vitro activity and a good cell safety index. By use of support vector analysis, a quantitative structure activity relationship (QSAR) model was obtained, showing good predictive models for cell safety. We conclude by updating the mode of action of the thiazolides and explain the candidate selection that has led to compound 4 entering preclinical development.
• 1-(Trifluoromethyl)ethenyl phenyl selenide and 1-(trifluoromethyl)ethenyl phenyl sulfide
  作者：Andrew E. Feiring

  DOI：10.1021/jo01298a041

  日期：1980.5
• FEIRING ANDREW E., J. ORG. CHEM., 1980, 45, NO 10, 1962-1964
  作者：FEIRING ANDREW E.

  DOI：——

  日期：——
• α- or β-trifluoromethyl epoxysulfones: New C3 reagents for heterocyclisation
  作者：Frédéric Laduron、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/0022-1139(94)03212-i

  日期：1995.7

  The syntheses of alpha- and beta-trifluoromethyl epoxysulfones 1 and 2 are described. Compound 1 reacts with nucleophiles and bis-nucleophiles to furnish trifluoromethyl ketones and triRuoromethyl heterocycles in good yield, while its isomer 2 leads to the opposite thiazole regioisomers with thioamides.