PhCH2SSO2CF3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: PhCH2SSO2CF3
• 英文别名: Trifluoromethylsulfonylsulfanylmethylbenzene
• 化学式: C₈H₇F₃O₂S₂
• 分子量: 256.27
• InChiKey: WTHJGUSKVVDUDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(hydridotris(3,5-diisopropylpyrazolyl)borate)Zn(hydrogensulfido)] 、 PhCH2SSO2CF3 在 N(CH₂CH₃)3 作用下， 以 二氯甲烷-D2 为溶剂， 生成 [(hydridotris(3,5-diisopropylpyrazolyl)borate)Zn(trifluoromethanesulfinate)]
  参考文献：
  名称：

  Synthesis, Characterization, and Reactivity of Alkyldisulfanido Zinc Complexes

  摘要：

  The alkyldisulfanido zinc complexes Tp(iPr,iPr) n(SSR) and Tp(Ph,Me) n(SSR) where Tp(iPr,iPr) is hydridotris-((3,5-isopropyl) pyrazolyl)borate, Tp(Ph,Me) is hydridotris-((3-phenyl,5-methyl)pyrazolyl)borate, and (SSR) is tert-butyldisulfanido or triphenylmethanedisulfanido were synthesized by reaction between the corresponding hydroxo complexes Tp n(OH) and the synthetic persulfide RSSH. All the complexes were characterized by elemental analysis and H-1 NMR spectroscopy, and representative members of the class were also structurally characterized. The reactivity of the alkyldisulfanido Tp n(SSR) complexes with thiols was studied. In the absence of base, a simple exchange reaction between the alkyldisulfanido ligand and the thiol was observed in dichloromethane; when in the presence of base, the corresponding hydrogen(sulfido) complexes Tp n(SH) were obtained. The mechanism of the latter reaction has been studied and does not involve the coordinated alkyldisulfanido group. Reaction of the hydrogen(sulfido) complexes Tp(iPr,iPr) n(SH) with the thiosulfonate PhCH2S-SO2CF3 did not yield the expected alkyldisulfanido complex but benzyltrisulfide and a new complex tentatively assigned as Tp(iPr,iPr) n(O2SCF3).

  DOI：

  10.1021/ic900238v
• 作为产物：
  描述：

  二苄基二硫 、 Langlois reagent 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到PhCH2SSO2CF3
  参考文献：
  名称：

  氧化条件下三氟甲磺酸硫酯和硒酸酯的新合成

  摘要：

  三氟甲硫基（或硒代）磺酸盐（CF 3 SO 2 YR，Y = S，Se）易于在0–20°C的一步中由二硫化物（或二硒化物），三氟甲亚磺酸钠和[双-（三氟乙酰氧基）碘]制得。苯（BTIB）。

  DOI：

  10.1016/s0022-1139(97)00009-2

文献信息

• Synthetic Uses of Thio- and Selenoesters of Trifluoromethylated Acids. 1. Preparation of Trifluoromethyl Sulfides and Selenides
  作者：Thierry Billard、Nicolas Roques、Bernard R. Langlois

  DOI：10.1021/jo980649a

  日期：1999.5.1

  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.
• A New Route to Thio- and Selenosulfonates from Disulfides and Diselenides. Application to the Synthesis of New Thio- and Selenoesters of Triflic Acid
  作者：Thierry Billard、Bernard R. Langlois、Sylvie Large、Daniel Anker、Nathalie Roidot、Philippe Roure

  DOI：10.1021/jo960619c

  日期：1996.1.1

  Alkyl and aryl trifluoromethanethiosulfonates(1) (or selenosulfonates) were prepared in one step either from alkyl and aryl sulfenyl (or selenenyl) chlorides and sodium trifluoromethanesulfinate (3) or, more generally, from disulfides (or diselenides), 3, and bromine. The second method involved trifluoromethanesulfonyl bromide as key intermediate. Benzenethiosulfonates were obtained in a similar way from disulfides, benzenesulfinate, and bromine but benzeneselenosulfonates could not be obtained by the same method from diselenides.
• Synthesis, Characterization, and Reactivity of Alkyldisulfanido Zinc Complexes
  作者：Erwan Galardon、Alain Tomas、Mohamed Selkti、Pascal Roussel、Isabelle Artaud

  DOI：10.1021/ic900238v

  日期：2009.7.6

  The alkyldisulfanido zinc complexes Tp(iPr,iPr) n(SSR) and Tp(Ph,Me) n(SSR) where Tp(iPr,iPr) is hydridotris-((3,5-isopropyl) pyrazolyl)borate, Tp(Ph,Me) is hydridotris-((3-phenyl,5-methyl)pyrazolyl)borate, and (SSR) is tert-butyldisulfanido or triphenylmethanedisulfanido were synthesized by reaction between the corresponding hydroxo complexes Tp n(OH) and the synthetic persulfide RSSH. All the complexes were characterized by elemental analysis and H-1 NMR spectroscopy, and representative members of the class were also structurally characterized. The reactivity of the alkyldisulfanido Tp n(SSR) complexes with thiols was studied. In the absence of base, a simple exchange reaction between the alkyldisulfanido ligand and the thiol was observed in dichloromethane; when in the presence of base, the corresponding hydrogen(sulfido) complexes Tp n(SH) were obtained. The mechanism of the latter reaction has been studied and does not involve the coordinated alkyldisulfanido group. Reaction of the hydrogen(sulfido) complexes Tp(iPr,iPr) n(SH) with the thiosulfonate PhCH2S-SO2CF3 did not yield the expected alkyldisulfanido complex but benzyltrisulfide and a new complex tentatively assigned as Tp(iPr,iPr) n(O2SCF3).
• A new synthesis of thioesters and selenoesters of triflic acid under oxidative conditions
  作者：Thierry Billard、Bernard R. Langlois

  DOI：10.1016/s0022-1139(97)00009-2

  日期：1997.8

  Trifluoromethanethio-(or seleno-)sulfonates (CF3SO2YR, Y=S, Se) are easily obtained in one step at 0–20 °C from disulfides (or diselenides), sodium trifluoromethanesulfinate and [bis-(trifluoroacetoxy)iodo]benzene (BTIB).

  三氟甲硫基（或硒代）磺酸盐（CF 3 SO 2 YR，Y = S，Se）易于在0–20°C的一步中由二硫化物（或二硒化物），三氟甲亚磺酸钠和[双-（三氟乙酰氧基）碘]制得。苯（BTIB）。