(3S,6S,9S)-1-aza-2-oxo-3-aminocarbonyl-3-(1'-naphthylmethyl)-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane | 208455-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (3S,6S,9S)-1-aza-2-oxo-3-aminocarbonyl-3-(1'-naphthylmethyl)-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane
• CAS: 208455-25-8
• 化学式: C₂₅H₃₀N₂O₄
• 分子量: 422.524
• InChiKey: MDESCLIYFIUTOY-AOUJKTHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  89.7
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,6S,9S)-1-aza-2-oxo-3-aminocarbonyl-3-(1'-naphthylmethyl)-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane 在 sodium hydroxide 、 benzyltrimethylammonium tribromide 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以40%的产率得到(3R,6S,9S)-1-aza-2-oxo-3-amino-3-(1'-naphthylmethyl)-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：

  (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester 在 4-二甲氨基吡啶 、 氰化钠 、 氨 、 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 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 129.0h， 生成 (3S,6S,9S)-1-aza-2-oxo-3-aminocarbonyl-3-(1'-naphthylmethyl)-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