(3R,6S,9S)-1-aza-2-oxo-3-methoxycarbonyl-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane | 208455-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,6S,9S)-1-aza-2-oxo-3-methoxycarbonyl-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane
• 英文别名: 3-O-tert-butyl 6-O-methyl (3S,6R,8aS)-6-benzyl-5-oxo-1,2,3,7,8,8a-hexahydroindolizine-3,6-dicarboxylate
• CAS: 208455-21-4
• 化学式: C₂₂H₂₉NO₅
• 分子量: 387.476
• InChiKey: ADKXRUOEFIFTST-HYFFOGBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,6S,9S)-1-aza-2-oxo-3-methoxycarbonyl-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane 在 sodium hydroxide 、 benzyltrimethylammonium tribromide 、 氰化钠 、 氨 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 108.0h， 生成 (3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane
  参考文献：
  名称：

  Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics

  摘要：

  A flexible stereoselective synthetic scheme was developed to prepare 6,5-fused bicyclic lactams, that molecular mechanics calculations revealed to have a potential as reverse-turn mimetics. The convergence of the synthetic sequence was achieved by attachment of a properly substituted malonate unit to the (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester, Stereoselective intramolecular alkylation of the malonate afforded the 6-membered lactam fused to the 2-carbalkoxy pyrrolidine nucleus. X-ray diffraction analysis of a more advanced synthetic derivative allowed the unequivocal assignment of the configuration at the newly created quaternary stereocenter as R. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00207-5
• 作为产物：
  描述：

  2-benzyl-3-methoxy-3-oxopropanoic acid 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 33.0h， 生成 (3R,6S,9S)-1-aza-2-oxo-3-methoxycarbonyl-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane
  参考文献：
  名称：

  Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics

  摘要：

  A flexible stereoselective synthetic scheme was developed to prepare 6,5-fused bicyclic lactams, that molecular mechanics calculations revealed to have a potential as reverse-turn mimetics. The convergence of the synthetic sequence was achieved by attachment of a properly substituted malonate unit to the (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester, Stereoselective intramolecular alkylation of the malonate afforded the 6-membered lactam fused to the 2-carbalkoxy pyrrolidine nucleus. X-ray diffraction analysis of a more advanced synthetic derivative allowed the unequivocal assignment of the configuration at the newly created quaternary stereocenter as R. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00207-5

文献信息

• Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics
  作者：Lino Colombo、Marcello Di Giacomo、Gloria Brusotti、Nicola Sardone、Mauro Angiolini、Laura Belvisi、Sonia Maffioli、Leonardo Manzoni、Carlo Scolastico

  DOI：10.1016/s0040-4020(98)00207-5

  日期：1998.5

  A flexible stereoselective synthetic scheme was developed to prepare 6,5-fused bicyclic lactams, that molecular mechanics calculations revealed to have a potential as reverse-turn mimetics. The convergence of the synthetic sequence was achieved by attachment of a properly substituted malonate unit to the (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester, Stereoselective intramolecular alkylation of the malonate afforded the 6-membered lactam fused to the 2-carbalkoxy pyrrolidine nucleus. X-ray diffraction analysis of a more advanced synthetic derivative allowed the unequivocal assignment of the configuration at the newly created quaternary stereocenter as R. (C) 1998 Elsevier Science Ltd. All rights reserved.