(-)-(1S,2S)-1,2-bis(2-pyridylsulfanyl)cyclohexane | 1351099-47-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (-)-(1S,2S)-1,2-bis(2-pyridylsulfanyl)cyclohexane
• 英文别名: trans-1,2-bis(2-pyridylthio)cyclohexane
• CAS: 1351099-47-2
• 化学式: C₁₆H₁₈N₂S₂
• 分子量: 302.464
• InChiKey: ZOHJHJNWDMFFDK-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  trans-1,2-cyclohexandiol 、 2,2'-二硫二吡啶 在 三丁基膦 作用下， 以 甲苯 为溶剂， 以62%的产率得到(-)-(1S,2S)-1,2-bis(2-pyridylsulfanyl)cyclohexane
  参考文献：
  名称：

  Enantiopure trans-1-amino-2-(arylsulfanyl)cyclohexanes: novel chiral motifs for ligands and organocatalysts

  摘要：

  In order to obtain the title compounds (1R,2R)-cyclohexane-1,2-diol was stereoselectively converted into cis-(1R,2S)-2-(arylsulfanyl)cyclohexanols and these products were submitted to the nucleophilic substitution via the Mitsunobu reaction (HN3, DEAD). Reduction of the isolated azides gave the desired trans-(1S,2S)-1-amino-2-(arylsulfanyl)cyclohexanes. The (1S,2S)-1-amino-2-(2-aminophenylsulfanyl)cyclohexanes thus prepared were reacted with 3,5-bis(trifluoromethyl)phenyl isothiocyanate to furnish the respective bis-thiourea compounds. An application of a derivative of this type as an organocatalyst (20 mol %) in the Baylis-Hillman reaction gave the respective product in up to 93% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.09.015

文献信息

• Metal Cation-Exchanged Montmorillonite-Catalyzed Addition of Organic Disulfides to Alkenes
  作者：Takahiro Nishimura、Tomoaki Yoshinaka、Sakae Uemura

  DOI：10.1246/bcsj.78.1138

  日期：2005.6

  The addition of organic disulfides to alkenes, giving vic-bis(alkylthio)alkanes and vic-bis(arylthio)alkanes, proceeds in chlorobenzene in the presence of a catalytic amount of a variety of metal c...

  有机二硫化物与烯烃的加成，得到 vic-双（烷硫基）烷烃和 vic-双（芳硫基）烷烃，在催化量的各种金属化合物存在下，在氯苯中进行。