tert-butyl N-[(2S)-4-nitro-1-phenylbutan-2-yl]carbamate | 182937-19-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[(2S)-4-nitro-1-phenylbutan-2-yl]carbamate
• CAS: 182937-19-5
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: ZAKYLLIXPJSZKM-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-4-nitro-1-phenylbutan-2-yl]carbamate 在 4-二甲氨基吡啶 、 aluminum oxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of novel, pseudo C2 symmetric inhibitors of HIV protease

  摘要：

  A novel series of chain-extended, pseudo C2 symmetric 1,5-diaminoalcohol analogs was designed and synthesized using an efficient nitroaldol condensation mediated by triethylsilyl triflate and TBAF.xH(2)O. Prototypical acyclic compounds harboring a central spirolactam or a nitro group, and amide variants of an off-center 1,5-diaminoalcohol analog were synthesized and their activities against HIV protease evaluated. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00392-7
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 在 sodium tetrahydroborate 、 四丁基氟化铵 、 silica gel 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 异丙醇 为溶剂， 生成 tert-butyl N-[(2S)-4-nitro-1-phenylbutan-2-yl]carbamate
  参考文献：
  名称：

  Design and synthesis of novel, pseudo C2 symmetric inhibitors of HIV protease

  摘要：

  A novel series of chain-extended, pseudo C2 symmetric 1,5-diaminoalcohol analogs was designed and synthesized using an efficient nitroaldol condensation mediated by triethylsilyl triflate and TBAF.xH(2)O. Prototypical acyclic compounds harboring a central spirolactam or a nitro group, and amide variants of an off-center 1,5-diaminoalcohol analog were synthesized and their activities against HIV protease evaluated. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00392-7

文献信息

• [EN] PROCESS FOR STEREOSELECTIVE PREPARATION OF AN INTERMEDIATE OF PROTEASE INHIBITORS<br/>[FR] PROCÉDÉ DE PRÉPARATION STÉRÉOSÉLECTIVE D'UN INTERMÉDIAIRE D'INHIBITEURS DE PROTÉASES
  申请人：PIRAMAL HEALTHCARE LTD

  公开号：WO2010143150A2

  公开（公告）日：2010-12-16

  The present invention provides a process for stereoselective preparation of N-[(1S,2R)-2- hydroxy-3-nitro-l-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester (nitroalcohol) comprising asymmetric reduction of the carbonyl group in [(1S)-3-nitro-2- oxo-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester (nitroketone) using sodium borohydride as the reducing agent in a solvent mixture of an alcohol and a halogenated solvent at a temperature ranging from -15°C to 00C to yield nitroalcohol in > 78 % yield and > 99 % chiral purity.