1,2-bis(phenylsulfanyl)cyclohexane | 71778-43-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,2-bis(phenylsulfanyl)cyclohexane
• 英文别名: 1,2-bis(phenylsulfinyl)cyclohexane；1,1'-[Cyclohexane-1,2-diylbis(thio)]dibenzene；(2-phenylsulfanylcyclohexyl)sulfanylbenzene
• CAS: 71778-43-3
• 化学式: C₁₈H₂₀S₂
• 分子量: 300.489
• InChiKey: HUUJXLSDFWKQKF-UHFFFAOYSA-N

物化性质

• 沸点：
  185-196 °C(Press: 0.1 Torr)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(phenylsulfanyl)cyclohexane 在 bis(acetylacetonate)oxovanadium 、 (S)-2-((1-hydroxy-3-methylbutan-2-ylimino)methyl)-4,6-diiodophenol 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.17h， 以15%的产率得到(1R,2R,S[S],S[S])-1,2-bis(phenylsulfinyl)cyclohexane
  参考文献：
  名称：

  An Effective Deracemization of trans-1,2-Bis (phenylsulfenyl)cyclohexane

  摘要：

  A chiral S,S-donating C2-symmetric ligand containing two stereogenic centers was prepared from rac-trans-1,2-cyclohexanediol. An effective deracemization of trans-1,2-bis(phenylsulfenyl)cyclohexane was achieved by the catalyzed enantioselective sulfoxidation, followed by the chromatographic separation of diastereomeric mono- and bis-sulfoxides. Subsequent recrystallization of enantiomerically enriched bissulfoxide and its final deoxygenation gave optically pure (1R,2R)-bis(phenylsulfenyl)cyclohexane.

  DOI：

  10.1080/10426500902856420
• 作为产物：
  描述：

  二苯二硫醚 、 环己烯 在 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以25%的产率得到1,2-bis(phenylsulfanyl)cyclohexane
  参考文献：
  名称：

  Iodine-catalyzed disulfidation of alkenes

  摘要：

  The disulfidation reactions of alkenes with disulfides were thoroughly investigated in this paper. Using H(2)O or DCE as the solvent, most reactions occurred smoothly to give the corresponding disulfidated products in good to high yields at room temperature within 12 h. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.081

文献信息

• DEOXYGENATIVE THIOACETALIZATION OF CARBONYL COMPOUNDS WITH ORGANIC DISULFIDE AND TRIBUTYLPHOSPHINE
  作者：Masato Tazaki、Makoto Takagi

  DOI：10.1246/cl.1979.767

  日期：1979.7.5

  A new deoxygenative thioether formation from carbonyl compounds as well as epoxides is presented (eq. 1–3). The reaction proceeds with the combined use of alkyl or aryl disulfide and tributylphosphine under neutral and mild conditions. The reaction with aldehydes proceeds with special ease to give thioacetals in high yields, and can be a valuable synthetic reaction.

  提出了一种由羰基化合物和环氧化物形成的新脱氧硫醚（方程式 1-3）。在中性和温和条件下，该反应在烷基或芳基二硫化物和三丁基膦的组合使用下进行。与醛的反应特别容易以高产率得到硫代缩醛，并且可以是有价值的合成反应。
• One-step, Enantiospecific Transformationof Cyclic, Five-membered-1,2-diols into their Respective 1,2-Bis(phenylsulfanyl)Derivatives
  作者：Jacek Skarżewski、Anil Gupta、Elżbieta Wojaczyńska、Renata Siedlecka

  DOI：10.1055/s-2003-41015

  日期：——

  The enantiomeric cyclic, five-membered vic-diolsreacted with (PhS)2/Bu3P in benzeneat 80 °C giving the corresponding bis(phenylsulfanyl) derivatives(42-74%) with complete inversion of configurationat both stereogenic centers. Similar reaction conditions were alsosuccessfully used for the enantiospecific transformation of a singlehydroxy group into the respective enantiomeric thioether function.For other vic-diols the neighboring groupparticipation hampered the stereoselectivity of the double substitution.

  对映体环状五元沧二醇与 (PhS)2/Bu3P 在苯中于 80 °C 发生反应，生成相应的双（苯硫基）衍生物（42-74%），两个立体中心的构型完全反转。类似的反应条件也成功地用于将单羟基对映体转化为相应对映体的硫醚官能团。
• TAZAKI MASATO; TAKAGI MAKOTO, CHEM. LETT., 1979, NO 7, 767-770
  作者：TAZAKI MASATO、 TAKAGI MAKOTO

  DOI：——

  日期：——
• An Effective Deracemization of <i>trans</i>-1,2-Bis (phenylsulfenyl)cyclohexane
  作者：Elżbieta Wojaczyńska、Jacek Skarżewski

  DOI：10.1080/10426500902856420

  日期：2009.5.14

  A chiral S,S-donating C2-symmetric ligand containing two stereogenic centers was prepared from rac-trans-1,2-cyclohexanediol. An effective deracemization of trans-1,2-bis(phenylsulfenyl)cyclohexane was achieved by the catalyzed enantioselective sulfoxidation, followed by the chromatographic separation of diastereomeric mono- and bis-sulfoxides. Subsequent recrystallization of enantiomerically enriched bissulfoxide and its final deoxygenation gave optically pure (1R,2R)-bis(phenylsulfenyl)cyclohexane.
• Iodine-catalyzed disulfidation of alkenes
  作者：Xiu-Ren Wang、Fan Chen

  DOI：10.1016/j.tet.2011.04.081

  日期：2011.6

  The disulfidation reactions of alkenes with disulfides were thoroughly investigated in this paper. Using H(2)O or DCE as the solvent, most reactions occurred smoothly to give the corresponding disulfidated products in good to high yields at room temperature within 12 h. (C) 2011 Elsevier Ltd. All rights reserved.