(-)-(3S,4aS,8aS,2'R,3'S)-2-[3'-bromo-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide | 1014685-47-2

• 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: (-)-(3S,4aS,8aS,2'R,3'S)-2-[3'-bromo-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide
• 英文别名: (3S,4aS,8aS)-2-[(2R,3S)-3-bromo-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide
• CAS: 1014685-47-2
• 化学式: C₂₄H₃₇BrN₂O₂
• 分子量: 465.474
• InChiKey: HAIYKPPANCVTIC-LILSUDLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(3S,4aS,8aS,2'R,3'S)-2-[3'-bromo-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide 在 sodium azide 、 18-冠醚-6 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 48.0h， 以72%的产率得到(3S,4aS,8aS,2'R,3'R)-2-[3'-azido-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir

  摘要：

  A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidomimetics with various residues. Finally the total synthesis of two diastereoisomer analogues of HIV-Protease inhibitor Saquinavir has been achieved and their biological activity evaluated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.020
• 作为产物：
  描述：

  (-)-(3S,4aS,8aS,2'R,3'R)-2-[2',3'-epoxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide 在 magnesium bromide 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以68%的产率得到(-)-(3S,4aS,8aS,2'R,3'S)-2-[3'-bromo-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  MgBr 2介导的2,3-三元杂环胺的打开

  摘要：

  描述了可商购的MgBr 2对2，3-环氧胺和2，3-氮丙啶胺的区域和立体控制的打开。据报道，这种新方法可能代表了制备有前途的中间体的一般和有用的方法。而且，在特定情况下，反应发展为令人感兴趣的恶唑烷丁-2-酮结构。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.354

文献信息

• Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir
  作者：Giuliana Righi、Simona Ciambrone、Carlo Bonini、Pietro Campaner

  DOI：10.1016/j.bmc.2007.10.020

  日期：2008.1

  A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidomimetics with various residues. Finally the total synthesis of two diastereoisomer analogues of HIV-Protease inhibitor Saquinavir has been achieved and their biological activity evaluated. (C) 2007 Elsevier Ltd. All rights reserved.
• MgBr₂-mediated opening of 2,3-three membered heterocyclic amines
  作者：Giuliana Righi、Simona Ciambrone、Evelina Esuperanzi、Francesca Montini、Romina Pelagalli

  DOI：10.1002/jhet.354

  日期：——

  Regio- and stereo-controlled opening of 2,3-epoxy amines and 2,3-aziridine amines by the commercially available MgBr2 is described. As reported, this new method could represent a general and useful approach for the preparation of promising intermediates. Moreover, in particular cases, the reaction evolves toward an interesting oxazolidin-2-one structure. J. Heterocyclic Chem., (2010).

  描述了可商购的MgBr 2对2，3-环氧胺和2，3-氮丙啶胺的区域和立体控制的打开。据报道，这种新方法可能代表了制备有前途的中间体的一般和有用的方法。而且，在特定情况下，反应发展为令人感兴趣的恶唑烷丁-2-酮结构。J.杂环化​​学。（2010）。