(S)-1-Amino-pentane-2-thiol | 791048-55-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: (S)-1-Amino-pentane-2-thiol
• 英文别名: (2S)-1-aminopentane-2-thiol
• CAS: 791048-55-0
• 化学式: C₅H₁₃NS
• 分子量: 119.231
• InChiKey: QCRMUEMAFOAZPC-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  光气 、 (S)-1-Amino-pentane-2-thiol 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (S)-5-Propyl-thiazolidin-2-one
  参考文献：
  名称：

  Stereoselective follow-up reactions of (S)-2-sulfanyl nitriles

  摘要：

  Follow-up reactions of (S)-2-acetylthionitriles (S)-2 and (S)-2-benzylthionitriles (S)-4, respectively, are described. (S)-2-Acetylthionitriles were converted via Pinner reaction to ethyl (S)-2-mercaptocarboxylates (S)-3 almost without racemization. Two routes for the stereoselective preparation of 1,2-amino thiols (S)-5 have been investigated. Hydrogenation of (S)-2 with BH3. THF gave (S)-5 which, however, could not be isolated directly under the reaction conditions, but, by reaction with phosgene in an alkaline medium, the 1,2-amino thiols (S)-5 could be trapped as (S)-5-alkylthiazolidinones (S)-7 in good yields without racemization. (S)-Benzylthioamines (S)-6, derived from (S)-4 by hydrogenation with LiAlH4, were debenzylated with sodium in NH3 to give (S)-5 which were isolated as hydrochlorides with high enantiomeric excesses. Optically active thiomorpholines (S)-12 are accessible starting from (S)-2-(2-hydroxyethylthio)nitriles (S)-10 which are first chlorinated with SOCl2 to yield (S)-2-(2-chloroethylthio)nitriles (S)-11 which after hydrogenation with LiAlH4 cyclize to give thiomorpholines (S)-12. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00155-x
• 作为产物：
  描述：

  (S)-2-acetylthiopentanenitrile 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 (S)-1-Amino-pentane-2-thiol
  参考文献：
  名称：

  Stereoselective follow-up reactions of (S)-2-sulfanyl nitriles

  摘要：

  Follow-up reactions of (S)-2-acetylthionitriles (S)-2 and (S)-2-benzylthionitriles (S)-4, respectively, are described. (S)-2-Acetylthionitriles were converted via Pinner reaction to ethyl (S)-2-mercaptocarboxylates (S)-3 almost without racemization. Two routes for the stereoselective preparation of 1,2-amino thiols (S)-5 have been investigated. Hydrogenation of (S)-2 with BH3. THF gave (S)-5 which, however, could not be isolated directly under the reaction conditions, but, by reaction with phosgene in an alkaline medium, the 1,2-amino thiols (S)-5 could be trapped as (S)-5-alkylthiazolidinones (S)-7 in good yields without racemization. (S)-Benzylthioamines (S)-6, derived from (S)-4 by hydrogenation with LiAlH4, were debenzylated with sodium in NH3 to give (S)-5 which were isolated as hydrochlorides with high enantiomeric excesses. Optically active thiomorpholines (S)-12 are accessible starting from (S)-2-(2-hydroxyethylthio)nitriles (S)-10 which are first chlorinated with SOCl2 to yield (S)-2-(2-chloroethylthio)nitriles (S)-11 which after hydrogenation with LiAlH4 cyclize to give thiomorpholines (S)-12. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00155-x

文献信息

• Stereoselective follow-up reactions of (S)-2-sulfanyl nitriles
  作者：Sebastian Gaupp、Franz Effenberger

  DOI：10.1016/s0957-4166(99)00155-x

  日期：1999.5

  Follow-up reactions of (S)-2-acetylthionitriles (S)-2 and (S)-2-benzylthionitriles (S)-4, respectively, are described. (S)-2-Acetylthionitriles were converted via Pinner reaction to ethyl (S)-2-mercaptocarboxylates (S)-3 almost without racemization. Two routes for the stereoselective preparation of 1,2-amino thiols (S)-5 have been investigated. Hydrogenation of (S)-2 with BH3. THF gave (S)-5 which, however, could not be isolated directly under the reaction conditions, but, by reaction with phosgene in an alkaline medium, the 1,2-amino thiols (S)-5 could be trapped as (S)-5-alkylthiazolidinones (S)-7 in good yields without racemization. (S)-Benzylthioamines (S)-6, derived from (S)-4 by hydrogenation with LiAlH4, were debenzylated with sodium in NH3 to give (S)-5 which were isolated as hydrochlorides with high enantiomeric excesses. Optically active thiomorpholines (S)-12 are accessible starting from (S)-2-(2-hydroxyethylthio)nitriles (S)-10 which are first chlorinated with SOCl2 to yield (S)-2-(2-chloroethylthio)nitriles (S)-11 which after hydrogenation with LiAlH4 cyclize to give thiomorpholines (S)-12. (C) 1999 Elsevier Science Ltd. All rights reserved.