(S)-2-(mercaptomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine | 188625-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-2-(mercaptomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine
• 英文别名: N-Boc-pyrrolidinemethanethiol；(S)-2-(mercaptomethyl)-1-[(tert-butyloxy)carbonyl]pyrrolidine；(S)-tert-Butyl 2-(mercaptomethyl)pyrrolidine-1-carboxylate；tert-butyl (2S)-2-(sulfanylmethyl)pyrrolidine-1-carboxylate
• CAS: 188625-66-3
• 化学式: C₁₀H₁₉NO₂S
• 分子量: 217.332
• InChiKey: FSQKKUYXPMRNJF-QMMMGPOBSA-N

物化性质

• 沸点：
  298.5±13.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(mercaptomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (S)-(+)-2-Pyrrolidinmethanthiol
  参考文献：
  名称：

  Chemical synthesis of N-peptidyl 2-pyrrolidinemethanethiol for peptide ligation

  摘要：

  Peptides carrying a C-terminal 2-pyrrolidinemethanethiol (PMT) unit were synthesized using 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS), and were shown to ligate efficiently with cysteinyl-peptides. This novel PMT-mediated ligation tolerated many different C-terminal residues and was successfully applied to a one-pot N-to-C sequential ligation reaction and the semi-synthesis of lysine 16 acetylated histone H4, demonstrating the utility of the method in peptide and protein synthesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.013
• 作为产物：
  描述：

  tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 18.0h， 生成 (S)-2-(mercaptomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine
  参考文献：
  名称：

  [EN] AMINOPYRIDINE COMPOUNDS AND METHODS FOR THE PREPARATION AND USE THEREOF
  [FR] COMPOSÉS AMINOPYRIDINE ET PROCÉDÉS POUR LEUR PRÉPARATION ET LEUR UTILISATION

  摘要：

  本发明一般涉及治疗靶向细菌Porphyromonas gingivalis的治疗药物，包括其蛋白酶精氨酸龈蛋白酶A/B（Rgp），以及它们用于治疗与P. gingivalis感染相关的疾病，包括脑部疾病如阿尔茨海默病。在某些实施例中，本发明提供根据本文所述的Formula I和Formula III的化合物，以及其药用可接受的盐。

  公开号：

  WO2018209132A1

文献信息

• Organic Base-Facilitated Thiol–Thioalkyne Reaction with Exclusive Regio- and Stereoselectivity
  作者：Yunxin Sun、Ningning Song、Yanchen Han、Shengtao Ding

  DOI：10.1021/acs.joc.3c01621

  日期：2023.11.3

  thioalkynes with exclusive stereoselectivity facilitated by an organic base, which could proceed exceedingly fast under ambient atmosphere and room temperature, affording β trans addition products in up to nearly quantitative yields. The dual nature of the sulfur atom in attracting and donating electrons is supposed to be pivotal in determining the regio- and stereoselectivity. This system tolerates a

  在这里，我们报道了富电子硫代炔的区域特异性氢硫基化，在有机碱的促进下具有独特的立体选择性，该反应可以在环境大气和室温下非常快地进行，以接近定量的产率提供β反式加成产物。硫原子吸引和提供电子的双重性质被认为是决定区域选择性和立体选择性的关键。该系统可耐受多种硫醇和硫炔，在聚合物合成中显示出巨大的潜力。
• Aminopyridine compounds and methods for the preparation and use thereof
  申请人：Cortexyme, Inc.

  公开号：US11059786B2

  公开（公告）日：2021-07-13

  The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis, including its proteases arginine gingipain A/B (Rgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I and Formula III, as described herein, and pharmaceutically acceptable salts thereof.

  本发明一般涉及针对牙龈卟啉单胞菌的治疗药物，包括其蛋白酶精氨酸龈脂酶A/B (Rgp)，及其用于治疗与牙龈卟啉单胞菌感染相关的疾病，包括脑部疾病，如阿尔茨海默氏症。在某些实施方案中，本发明提供了本文所述的根据式 I 和式 III 的化合物及其药学上可接受的盐。
• Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors
  作者：Ljubomir Isakovic、Oscar M. Saavedra、David B. Llewellyn、Stephen Claridge、Lijie Zhan、Naomy Bernstein、Arkadii Vaisburg、Nadine Elowe、Andrea J. Petschner、Jubrail Rahil、Norman Beaulieu、France Gauthier、A. Robert MacLeod、Daniel Delorme、Jeffrey M. Besterman、Amal Wahhab

  DOI：10.1016/j.bmcl.2009.03.132

  日期：2009.5

  Potent SAH analogues with constrained homocysteine units have been designed and synthesized as inhibitors of human DNMT enzymes. The five membered (2S,4S)-4-mercaptopyrrolidine-2-carboxylic acid, in 1a, was a good replacement for homocysteine, while the corresponding six-member counterpart was less active. Further optimization of 1a, changed the selectivity pro. le of these inhibitors. A Chloro substituent at the 2-position of 1a, compound 1d, retained potency against DNMT1, while N-6 alkylation, compound 7a, conserved DNMT3b2 activity. The concomitant substitutions of 1a at both 2- and N-6 positions reduced activity against both enzymes. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of and Asymmetric Cycloaddition with Chiral Diiron Acyl Complexes
  作者：Scott R. Gilbertson、Omar D. Lopez

  DOI：10.1021/ja964195f

  日期：1997.4.1
• Dae Yoon Chi; O'Neil; Anderson, Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 928 - 937
  作者：Dae Yoon Chi、O'Neil、Anderson、Welch、Katzenellenbogen

  DOI：——

  日期：——