1-chloro-2-trifluoromethylsulfenyl cyclohexane

• 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-chloro-2-trifluoromethylsulfenyl cyclohexane
• 英文别名: 1beta-[(Trifluoromethyl)thio]-2alpha-chlorocyclohexane；(1R,2R)-1-chloro-2-(trifluoromethylsulfanyl)cyclohexane
• 化学式: C₇H₁₀ClF₃S
• 分子量: 218.671
• InChiKey: ATTXNIPRGBFANT-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯环己基三氯甲基硫醚 在 (HF)10-pyridine 作用下， 反应 12.0h， 以83%的产率得到1-chloro-2-trifluoromethylsulfenyl cyclohexane
  参考文献：
  名称：

  Selective aliphatic fluorination by halogen exchange in mild conditions

  摘要：

  HF-Base media, in particular (HF)(10)-pyridine or (HF)(3)-triethylamine, allow aliphatic chlorine-fluorine exchanges on acid-sensitive molecules. Depending on the nature (pyridine or triethylamine), stoichiometry of the base and temperature, selective mono-, di-, or tri-chlorine-fluorine exchanges on trichloromethyl groups alpha to sulfur, oxygen and carbon atoms can be obtained. (C) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.10.006

文献信息

• Trifluoromethanesulfanylamides as Easy-to-Handle Equivalents of the Trifluoromethanesulfanyl Cation (CF₃S⁺): Reaction with Alkenes and Alkynes
  作者：Aurélien Ferry、Thierry Billard、Bernard R. Langlois、Eric Bacqué

  DOI：10.1002/anie.200903387

  日期：2009.10.26

  Making introductions: The CF3S unit can be added in an electrophilic fashion to alkenes and alkynes in reactions with trifluoromethanesulfanylamide reagents (see scheme; Ts=toluene‐4‐sulfonyl). The products obtained may be of interest, for example, in pharmaceutical chemistry and materials science.

  简介：CF 3 S单元可以在与三氟甲烷硫代酰胺试剂反应的情况下，以亲电方式添加到烯烃和炔烃中（见方案； Ts =甲苯-4-磺酰基）。所获得的产物可能是令人感兴趣的，例如，在药物化学和材料科学中。
• Catalytic addition of trihalogenomethanesulfenyl chlorides to olefinic compounds
  作者：A. Haas、M. Lieb、Yuanfa Zhang

  DOI：10.1016/s0022-1139(00)80889-1

  日期：1985.11

  Trifluoroacetic acid has been found to be an efficient catalyst for the addition of fluorochloromethanesulfenyl chlorides CFnCl3−nSCl (n = 1, 2, 3) to olefins such as cyclohexene, 1-hexene, allyl bromide and vinyl bromide. The reaction with cyclohexene led to trans adducts. The addition to asymmetrical olefins afforded a mixture of Markovnikov- and anti-Markovnikov oriented adducts. The factors influencing

  已发现三氟乙酸是将氟氯甲烷亚磺酰氯CF n Cl 3-n SCl（n = 1，2，3）加至烯烃如环己烯，1-己烯，烯丙基溴和乙烯基溴的有效催化剂。与环己烯的反应产生反式加合物。向不对称烯烃的加成提供了马尔可夫尼可夫和反马尔可夫尼可夫取向的加合物的混合物。讨论了影响反应过程的因素。
• First and second generation of trifluoromethanesulfenamide reagent: A trifluoromethylthiolating comparison
  作者：Quentin Glenadel、Sébastien Alazet、Thierry Billard

  DOI：10.1016/j.jfluchem.2015.06.007

  日期：2015.11

  Trifluoromethylthiolation of molecules is a more and more studied reaction. In particular, the direct electrophilic trifluoromethylthiolation plays an important role in this chemistry. Among the various developed reagents, trifluoromethanesulfenamides constitute an efficient family of reagents. However, no systematic comparison of these two generations has been realized. In this paper, the difference of reactivity of these reagents is studied towards various nucleophiles. (C) 2015 Elsevier B.V. All rights reserved.