(S)-2-benzyl-[N-(benzyloxycarbonyl)]propandiamine | 254990-84-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-benzyl-[N-(benzyloxycarbonyl)]propandiamine
• 英文别名: (S)-benzyl (3-amino-2-benzylpropyl)carbamate；benzyl N-[(2S)-2-(aminomethyl)-3-phenylpropyl]carbamate
• CAS: 254990-84-6
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: RBXDKLLIXLIYOC-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-benzyl-[N-(benzyloxycarbonyl)]propandiamine 在 palladium on activated charcoal N-甲基吗啉 、 (benzotriazolyl-1-oxy)tripyrrolidinophospho. hexafluorophosp 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (R)-2-benzyl-[N-(benzyloxycarbonyl)glycyl]-[N'-(tert-butoxycarbonyl)-D-alanyl]-1,3-propanediamine
  参考文献：
  名称：

  Synthesis of asymmetrized 2-benzyl-1,3-diaminopropane by a chemoenzymatic route: a tool for combinatorially developing peptidomimetics

  摘要：

  Both enantiomers of monoacetamide 5, together with 'dipeptides' 30a,b and monocarbamates 24, (R)-43 and (S)-43, all derived from 2-benzyl-1,3-diaminopropane 4, were synthesized by a chemoenzymatic route starting from the known monoacetate 12. The behaviour of 4 and of the bis(acylated) derivatives 8-11 with respect to hydrolytic enzymes is also presented, together with an extensive study on the configurational stability of monoacylated derivatives of 4. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00371-7
• 作为产物：
  描述：

  (S)-1-acetoxy-2-benzyl-3-(methanesulfonyloxy)propane 在 sodium hydroxide 、 sodium azide 、 lipase Amano P 、 pH 7 buffer 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.17h， 生成 (S)-2-benzyl-[N-(benzyloxycarbonyl)]propandiamine
  参考文献：
  名称：

  Synthesis of asymmetrized 2-benzyl-1,3-diaminopropane by a chemoenzymatic route: a tool for combinatorially developing peptidomimetics

  摘要：

  Both enantiomers of monoacetamide 5, together with 'dipeptides' 30a,b and monocarbamates 24, (R)-43 and (S)-43, all derived from 2-benzyl-1,3-diaminopropane 4, were synthesized by a chemoenzymatic route starting from the known monoacetate 12. The behaviour of 4 and of the bis(acylated) derivatives 8-11 with respect to hydrolytic enzymes is also presented, together with an extensive study on the configurational stability of monoacylated derivatives of 4. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00371-7

文献信息

• Enzymatic Desymmetrization of Prochiral 2-Substituted-1,3-Diamines: Preparation of Valuable Nitrogenated Compounds
  作者：Nicolás Ríos-Lombardía、Eduardo Busto、Eduardo García-Urdiales、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1021/jo8025912

  日期：2009.3.20

  A wide range of prochiral 1,3-diamines were first efficiently synthesized and subsequently desymmetrized by using lipase from Pseudomonas cepacia as catalyst and diallyl carbonate as alkoxycarbonylating agent. In all cases, the amino carbamates of R-configuration were recovered. Final selective cleavage of the N-allyloxycarbonyl moiety was carried out under mild reaction conditions, which demonstrates

  首先有效地合成了多种前手性的1,3-二胺，然后使用洋葱假单胞菌的脂肪酶作为催化剂，碳酸二烯丙酯作为烷氧基羰基化剂进行了脱对称。在所有情况下，都回收了R-构型的氨基氨基甲酸酯。N-烯丙氧羰基部分的最终选择性裂解是在温和的反应条件下进行的，这表明该化学酶促途径具有很高的通用性和潜力，可作为相关旋光性氮化衍生物合成中的中间体来源。
• Chemical compounds
  申请人：AstraZeneca AB

  公开号：US10336725B2

  公开（公告）日：2019-07-02

  The present invention provides a compound of a formula (I): or a pharmaceutically acceptable salt thereof; a process for preparing such a compound; and to the use of such a compound in the treatment of an ENaC mediated disease state (such as asthma, CF or COPD).

  本发明提供了一种式 (I) 的化合物： 或其药学上可接受的盐；制备这种化合物的工艺；以及这种化合物在治疗 ENaC 介导的疾病（如哮喘、CF 或 COPD）中的用途。
• Chemical Compounds
  申请人：AstraZeneca AB

  公开号：US20170107195A1

  公开（公告）日：2017-04-20

  The present invention provides a compound of a formula (I): or a pharmaceutically acceptable salt thereof; a process for preparing such a compound; and to the use of such a compound in the treatment of an ENaC mediated disease state (such as asthma, CF or COPD).
• US9873678B2
  申请人：——

  公开号：US9873678B2

  公开（公告）日：2018-01-23
• Synthesis of asymmetrized 2-benzyl-1,3-diaminopropane by a chemoenzymatic route: a tool for combinatorially developing peptidomimetics
  作者：Luca Banfi、Giuseppe Guanti、Renata Riva

  DOI：10.1016/s0957-4166(99)00371-7

  日期：1999.9

  Both enantiomers of monoacetamide 5, together with 'dipeptides' 30a,b and monocarbamates 24, (R)-43 and (S)-43, all derived from 2-benzyl-1,3-diaminopropane 4, were synthesized by a chemoenzymatic route starting from the known monoacetate 12. The behaviour of 4 and of the bis(acylated) derivatives 8-11 with respect to hydrolytic enzymes is also presented, together with an extensive study on the configurational stability of monoacylated derivatives of 4. (C) 1999 Elsevier Science Ltd. All rights reserved.