tert-butyl (S)-(1-mercapto-4-methylpentan-2-yl)carbamate | 112157-38-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (S)-(1-mercapto-4-methylpentan-2-yl)carbamate
• 英文别名: tert-butyl N-[(2S)-4-methyl-1-sulfanylpentan-2-yl]carbamate
• CAS: 112157-38-7
• 化学式: C₁₁H₂₃NO₂S
• 分子量: 233.375
• InChiKey: RNMJAPKUHGNTBZ-VIFPVBQESA-N

物化性质

• 沸点：
  318.4±25.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-(1-mercapto-4-methylpentan-2-yl)carbamate 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 N-t-butoxycarbonyl-L-leucyl-Ψ(CH2S)-L-alanyl-α-azanorvaline benzyl ester
  参考文献：
  名称：

  Dutta, Anand S.; Giles, Michael, B.; Gormley, James J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 111 - 120

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 sodium hydroxide 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (S)-(1-mercapto-4-methylpentan-2-yl)carbamate
  参考文献：
  名称：

  C端亮氨酸硫醇作为阿片受体中硫醇基团探针的脑啡肽类似物的合成

  摘要：

  在 C 端具有硫醇基团的脑啡肽类似物 [D-Ala2, Leu(CH2SH)5] 脑啡肽被合成为阿片受体中必需硫醇基团的可能探针。为了保护亮氨酸硫醇的游离 SH 基团，从 L-亮氨酸（2-氨基-4-甲基-1-戊醇）制备氧化的 Boc-L-亮氨酸硫醇二聚体以延长脑啡肽序列。含 SH 的单体脑啡肽类似物是通过在 50% AcOH 中用锌处理从二聚体中获得的，它对 mu 阿片受体具有高亲和力。

  DOI：

  10.1246/cl.1987.997

文献信息

• Mild and selective silicon-mediated access to enantioenriched 1,2-mercaptoamines and β-amino arylchalcogenides
  作者：Damiano Tanini、Cosimo Borgogni、Antonella Capperucci

  DOI：10.1039/c9nj00657e

  日期：——

  Metal-free ring opening reactions of activated and unactivated aziridines with different silyl chalcogenides are described. Judicious tuning of the reaction conditions enables the synthesis of chiral enantioenriched N-Ts and N-Boc 1,2-mercaptoamines in good yields from the corresponding aziridines and bis(trimethylsilyl)sulfide. N-Protected and N-H unactivated aziridines are efficiently converted into

  描述了活化的和未活化的氮丙啶与不同的甲硅烷基硫属元素化物的无金属开环反应。通过适当调节反应条件，可以从相应的氮丙啶和双（三甲基甲硅烷基）硫化物以高收率合成手性对映体富集的N -Ts和N -Boc 1,2-巯基胺。用合适的芳族硫属元素硅烷处理后，N-保护的和N -H未活化的氮丙啶被有效地转化为相应的β-芳族硫属元素胺。硅介导的开环反应以优异的区域选择性和立体特异性进行，从而可以使用各种各样的合成和生物学上有价值的对映体富集的硫属元素胺。
• Synthesis of Enkephalin Analog with Leucinthiol at<i>C</i>-Terminus as Probe for Thiol Group in Opiate Receptors
  作者：Michio Kondo、Hiroaki Uchida、Hiroaki Kodama、Hiroshi Kitajima、Yasuyuki Shimohigashi

  DOI：10.1246/cl.1987.997

  日期：1987.5.5

  Enkephalin analog with thiol group at C-terminus, [D-Ala2, Leu(CH2SH)5]enkephalin, was synthesized as possible probe for the essential thiol group in opiate receptors. In order to protect the free SH group of leucinthiol, oxidized Boc-L-leucinthiol dimer was prepared from L-leucinol (2-amino-4-methyl-1-pentanol) to elongate the enkephalin sequence. SH-Containing monomeric enkephalin analog was obtained

  在 C 端具有硫醇基团的脑啡肽类似物 [D-Ala2, Leu(CH2SH)5] 脑啡肽被合成为阿片受体中必需硫醇基团的可能探针。为了保护亮氨酸硫醇的游离 SH 基团，从 L-亮氨酸（2-氨基-4-甲基-1-戊醇）制备氧化的 Boc-L-亮氨酸硫醇二聚体以延长脑啡肽序列。含 SH 的单体脑啡肽类似物是通过在 50% AcOH 中用锌处理从二聚体中获得的，它对 mu 阿片受体具有高亲和力。
• N-Chlorosuccinimide-Mediated Oxidative Chlorination of Thiols to Nα -Protected Amino Alkyl Sulfonyl Azides and Their Utility in the Synthesis of Sulfonyl Triazole Acids
  作者：Sharnabai. K. M、Krishnamurthy. M、Sagar. N. R、Santhosh. L、Vommina Sureshbabu

  DOI：10.2174/0929866523666161130151218

  日期：2016.12.13

  An efficient oxidative chlorination of thiols to Nα-protected amino alkyl sulfonyl azides is delineated. The reaction involves in situ generation of sulfonyl chloride employing Nchlorosuccinimide and tetrabutylammonium chloride-water in acetonitrile, followed by the reaction with sodium azide. The protocol is simple, straight forward, mild and high yielding. Amino acids with simple as well as bifunctional

  描绘了将硫醇有效氧化氯化为Nα-保护的氨基烷基磺酰基叠氮化物的方法。该反应包括使用NHC琥珀酰亚胺和四丁基氯化铵-水在乙腈中原位产生磺酰氯，然后与叠氮化钠反应。该方案简单，直接，温和且产率高。具有简单以及双官能侧链的氨基酸用于获得Nα-保护的氨基烷基磺酰基叠氮化物。此外，磺酰叠氮化物被用于通过Cu（OAc）2 .H 2 O / 2-氨基苯酚与丙酸催化的点击反应来合成非天然氨基酸。
• Simple Preparation of N-Protected Chiral β-Amino Alkyl Thiols from Corresponding Iodides Employing Sodium Trithiocarbonate
  作者：Chilakapati Madhu、H. P. Hemantha、T. M. Vishwanatha、V. V. Sureshbabu

  DOI：10.1080/00397911.2011.595522

  日期：2013.1

  Abstract A simple protocol for the preparation of N-protected amino alkyl thiols is reported that employs a reaction of sodium trithiocarbonate (Na2CS3) with N-protected amino alkyl iodides. Na2CS3 is easy to prepare and the protocol circumvents the use of strong bases and multiple steps. All the thiol compounds made were obtained as enantiopure samples and were characterized employing NMR and mass

  摘要报道了一种制备 N-保护的氨基烷基硫醇的简单方案，该方案采用三硫代碳酸钠 (Na2CS3) 与 N-保护的氨基烷基碘的反应。Na2CS3 易于制备，该协议避免使用强碱和多个步骤。制备的所有硫醇化合物均作为对映体纯样品获得，并使用 NMR 和质谱法进行表征。图形概要
• Mixed-inhibitor-prodrug as a new approach toward systemically active inhibitors of enkephalin-degrading enzymes
  作者：Marie Claude Fournie-Zaluski、Pascal Coric、Serge Turcaud、Evelyne Lucas、Florence Noble、Raphael Maldonado、Bernard P. Roques

  DOI：10.1021/jm00091a016

  日期：1992.6

  In order to evaluate the possible advantages of potentiating the effects of the endogenous enkephalins, to obtain analgesia without the serious drawbacks of morphine, it was essential to design systemically active compounds which inhibit the two metabolizing enzymes, aminopeptidase N (APN) and neutral endopeptidase 24.11 (NEP). A new concept combining the idea of "prodrug" and "mixed inhibitor" was therefore developed. Given the high efficiency of beta-mercaptoalkylamines as APN inhibitors and of N-(mercaptoacyl) amino acids as NEP inhibitors, compounds associating these molecules through disulfide or thioester bonds, which are known to increase lipophilicity and to favor passage across the blood-brain barrier, have been synthesized. An HPLC study indicated that the disulfide bridge was resistant to serum enzymes but was cleaved by brain membrane homogenates, suggesting that the active inhibitors were released in the central nervous system. The validity of the approach was verified by the efficient antinociceptive responses obtained in the hot plate test in mice after iv administration of disulfide-containing inhibitors (ED50s of from 4 to 26 mg/kg on the jump latency time). The analgesic potencies of the "mixed inhibitor-prodrug" RB 101 [H2NCH(CH2CH2SCH3)CH2SSCH2CH(CH2Ph)CONHCH(CH2Ph)COOCH2Ph] after iv administration were three times greater than those of a similar combined dose of its two constitutive moieties. The separation of the two diastereoisomers constituting RB 101 showed that the analgesia has a stereochemical dependence, the (S,S,S)-isomer being more active than the (S,R,S)-isomer. Furthermore, in the tail flick test in the rat, RB 101 gave 38% analgesia at a dose of 80 mg/kg. Due to its high efficiency and its longer pharmacological effect, RB 101 was selected for a complete study of its analgesic properties.