(+)-(1S,2S)-2-(2-aminophenylsulfanyl)cyclohexylamine | 1351099-55-2

• 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)-2-(2-aminophenylsulfanyl)cyclohexylamine
• 英文别名: 2-[(1S,2S)-2-aminocyclohexyl]sulfanylaniline
• CAS: 1351099-55-2
• 化学式: C₁₂H₁₈N₂S
• 分子量: 222.354
• InChiKey: DZBPHOGQWMKSOA-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2S)-2-(2-aminophenylsulfanyl)cyclohexylamine 、 硫代异氰酸苯酯 以 二氯甲烷 为溶剂， 以50%的产率得到(+)-1-phenyl-3-[(1S,2S)-2-({2-[(phenylcarbamothioyl)amino]phenyl}sulfanyl)cyclohexyl]thiourea
  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
• 作为产物：
  描述：

  (+)-(1S,2S)-trans-2-(2-aminophenylsulfanyl)cyclohexyl azide 在 甲醇 、 三苯基膦 作用下， 反应 2.0h， 以90%的产率得到(+)-(1S,2S)-2-(2-aminophenylsulfanyl)cyclohexylamine
  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

• Enantiopure trans-1-amino-2-(arylsulfanyl)cyclohexanes: novel chiral motifs for ligands and organocatalysts
  作者：Anna E. Nowak、Elżbieta Wojaczyńska、Jacek Skarżewski

  DOI：10.1016/j.tetasy.2011.09.015

  日期：2011.9

  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.