ethyl (R)-2-mercapto-4-methylpentanoate | 142843-05-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (R)-2-mercapto-4-methylpentanoate
• 英文别名: ethyl (2R)-4-methyl-2-sulfanylpentanoate
• CAS: 142843-05-8
• 化学式: C₈H₁₆O₂S
• 分子量: 176.28
• InChiKey: ZGEYSTOQBSXLFH-SSDOTTSWSA-N

物化性质

• 沸点：
  227.4±13.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (R)-2-mercapto-4-methylpentanoate 在 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 115.5h， 生成 {1-[1-{1-Cyclohexylmethyl-2-hydroxy-3-[3-methyl-1-(2-morpholin-4-yl-ethylcarbamoyl)-butane-1-sulfonyl]-propylcarbamoyl}-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Inhibitors of human renin with C-termini derived from amides and esters of .alpha.-mercaptoalkanoic acids

  摘要：

  New transition-state analogues bearing C-termini derived from alpha-mercaptoalkanoic acids, esters, and amides were prepared and evaluated as inhibitors of human renin. Addition of alpha-mercaptoalkanoate esters to a chiral Boc-amino epoxide intermediate led ultimately to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. The corresponding sulfoxide and sulfone analogues were also investigated. Some of these derivatives, including one with a stable BocPhe replacement, were relatively potent inhibitors of human plasma renin, having IC50 values below 10 nM. When selected compounds were administered intravenously to sodium-deficient rhesus monkeys (Macaca mulatta) at 0.06-1 mg/kg, they reduced plasma renin activity by 87-94%. However, the accompanying drop in blood pressure was of short duration.

  DOI：

  10.1021/jm00093a009
• 作为产物：
  描述：

  乙醇 、 (R)-2-mercapto-4-methylpentanoic acid 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以59%的产率得到ethyl (R)-2-mercapto-4-methylpentanoate
  参考文献：
  名称：

  Inhibitors of human renin with C-termini derived from amides and esters of .alpha.-mercaptoalkanoic acids

  摘要：

  New transition-state analogues bearing C-termini derived from alpha-mercaptoalkanoic acids, esters, and amides were prepared and evaluated as inhibitors of human renin. Addition of alpha-mercaptoalkanoate esters to a chiral Boc-amino epoxide intermediate led ultimately to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. The corresponding sulfoxide and sulfone analogues were also investigated. Some of these derivatives, including one with a stable BocPhe replacement, were relatively potent inhibitors of human plasma renin, having IC50 values below 10 nM. When selected compounds were administered intravenously to sodium-deficient rhesus monkeys (Macaca mulatta) at 0.06-1 mg/kg, they reduced plasma renin activity by 87-94%. However, the accompanying drop in blood pressure was of short duration.

  DOI：

  10.1021/jm00093a009

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.