(S)-1-Cbz-3-氨基吡咯烷盐酸盐 | 550378-39-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-Cbz-3-氨基吡咯烷盐酸盐
• 中文别名: (S)-1-苄氧羰基-3-氨基吡咯烷盐酸盐；(S)-3-氨基-1-Cbz-吡咯烷盐酸盐；(S)-3-氨基-1-苄氧羰基吡咯烷盐酸盐；(S)-N-CBZ-3-氨基吡咯烷；(S)-3-氨基-1-N-CBZ-吡咯烷盐酸盐
• 英文名称: (S)-benzyl 3-aminopyrrolidine-1-carboxylate hydrochloride
• 英文别名: 1-Cbz-3S-aminopyrrolidine hydrochloride；(S)-(+)-1-benzyloxycarbonyl-3-aminopyrrolidine hydrochloride；(S)-1-Cbz-3-Aminopyrrolidine hydrochloride；benzyl (3S)-3-aminopyrrolidine-1-carboxylate;hydrochloride
• CAS: 550378-39-7
• 化学式: C₁₂H₁₆N₂O₂*ClH
• 分子量: 256.732
• InChiKey: QNQVBYGRFHOBNO-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (S)-1-Cbz-3-氨基吡咯烷盐酸盐 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 (S)-benzyl 3-((S)-2-amino-2-cyclohexylacetamido)pyrrolidine-1-carboxylate hydrochloride
  参考文献：
  名称：

  Discovery of aminopiperidine-based Smac mimetics as IAP antagonists

  摘要：

  A series of structurally unique Smac mimetics that act as antagonists of inhibitor of apoptosis proteins (IAPs) has been discovered. While most previously described Smac mimetics contain the proline ring (or a similar cyclic motif) found in Smac, a key feature of the compounds described herein is that this ring has been removed. Despite this, compounds in this series potently bind to cIAP1 and elicit the expected phenotype of cIAP1 inhibition in cancer cells. Marked selectivity for cIAP1 over XIAP is observed for these compounds, which is attributed to a slight difference in the binding groove between the two proteins and the resulting steric interactions with the inhibitors. XIAP binding can be improved by constraining the inhibitor so that these unfavorable steric interactions are minimized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.109
• 作为产物：
  描述：

  氯甲酸苄酯 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-1-Cbz-3-氨基吡咯烷盐酸盐
  参考文献：
  名称：

  Discovery of aminopiperidine-based Smac mimetics as IAP antagonists

  摘要：

  A series of structurally unique Smac mimetics that act as antagonists of inhibitor of apoptosis proteins (IAPs) has been discovered. While most previously described Smac mimetics contain the proline ring (or a similar cyclic motif) found in Smac, a key feature of the compounds described herein is that this ring has been removed. Despite this, compounds in this series potently bind to cIAP1 and elicit the expected phenotype of cIAP1 inhibition in cancer cells. Marked selectivity for cIAP1 over XIAP is observed for these compounds, which is attributed to a slight difference in the binding groove between the two proteins and the resulting steric interactions with the inhibitors. XIAP binding can be improved by constraining the inhibitor so that these unfavorable steric interactions are minimized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.109

文献信息

• Antithrombotic agents
  申请人：——

  公开号：US20040010017A1

  公开（公告）日：2004-01-15

  This application relates to a compound of formula I (or a prodrug thereof or a pharmaceutically acceptable salt of the compound or prodrug thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

  本申请涉及到公式I的化合物（或其前药或其药学上可接受的盐或前药），如本文所定义，以及其药物组合物，以及其作为因子Xa抑制剂的用途，以及其制备方法和中间体。
• PREPARATION OF ALKYL ESTERS OF N-PROTECTED OXO-AZACYCLOALKYLCARBOXYLIC ACIDS
  申请人：Mangion Ian

  公开号：US20120053350A1

  公开（公告）日：2012-03-01

  A process for the preparation of alkyl esters of N-protected oxo-azacycloalkylcarboxylic acids of Formula III: comprises contacting a ketosulfoxonium ylide of Formula II: with an iridium catalyst to obtain Compound III, wherein P G1 is an amine protective group; k is 0, 1, or 2; and R U , R 1 , R 2 , and R 3 are defined herein. An embodiment of the process further com rises contacting a compound of Formula I: with a sulfoxonium halide of formula (R U ) 3 S(O)Z, wherein Z is halide, in the presence of a strong base to obtain Compound II. Additional embodiments add a series of process steps leading to the synthesis of 7-oxo-1,6-diazabicyclo[3.2.1]octanes suitable for use as β-lactamase inhibitors.

  一种制备式III的N-保护氧杂环烷基羧酸烷基酯的方法：包括将式II的酮亚磺酸叶立德与铱催化剂接触以获得化合物III，其中PG1为氨基保护基；k为0、1或2；RU、R1、R2和R3在此被定义。该方法的一种实施还包括将式I的化合物与式(RU)3S(O)Z的亚磺酸卤化物接触，在强碱存在下获得化合物II。其他实施例添加了一系列的过程步骤，可导致合成适用于作为β-内酰胺酶抑制剂的7-氧代-1,6-二氮杂双环[3.2.1]辛烷。
• [EN] PREPARATION OF ALKYL ESTERS OF N-PROTECTED OXO-AZACYCLOALKYLCARBOXYLIC ACIDS<br/>[FR] PRÉPARATION D'ESTERS ALKYLIQUES D'ACIDES OXO-AZACYCLOALKYLCARBOXYLIQUES N-PROTÉGÉS
  申请人：MERCK SHARP & DOHME

  公开号：WO2010126820A3

  公开（公告）日：2011-06-09
• ANTITHROMBOTIC AGENTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1311501B1

  公开（公告）日：2005-11-02
• US6924296B2
  申请人：——

  公开号：US6924296B2

  公开（公告）日：2005-08-02