(2S,6S,9S)-tert-butyl 2-oxo-3-(tert-butoxycarbonylamino)-1-azabicyclo[4.2.0]nonane-9-carboxylate | 296782-05-3

• 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: (2S,6S,9S)-tert-butyl 2-oxo-3-(tert-butoxycarbonylamino)-1-azabicyclo[4.2.0]nonane-9-carboxylate
• 英文别名: tert-butyl (3S,6S,8aS)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxylate
• CAS: 296782-05-3
• 化学式: C₁₈H₃₀N₂O₅
• 分子量: 354.447
• InChiKey: JRVWUVCLMXVQML-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,6S,9S)-tert-butyl 2-oxo-3-(tert-butoxycarbonylamino)-1-azabicyclo[4.2.0]nonane-9-carboxylate 在 三乙基硅烷 、 sodium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (3S,6S,9S)-2-oxo-3-(N-(9-fluorenylmethoxycarbonyl)amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid
  参考文献：
  名称：

  An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(N-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid

  摘要：

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.

  DOI：

  10.1021/jo0515935
• 作为产物：
  描述：

  Boc-L-焦谷氨酸甲酯 在 palladium on activated charcoal 氢气 、 caesium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -40.0 ℃ 、206.84 kPa 条件下， 反应 27.0h， 生成 (2S,6S,9S)-tert-butyl 2-oxo-3-(tert-butoxycarbonylamino)-1-azabicyclo[4.2.0]nonane-9-carboxylate
  参考文献：
  名称：

  An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(N-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid

  摘要：

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.

  DOI：

  10.1021/jo0515935

文献信息

• Synthesis of Azabicycloalkane Amino Acid Scaffolds as Reverse-Turn Inducer Dipeptide Mimics
  作者：Mauro Angiolini、Silvia Araneo、Laura Belvisi、Edoardo Cesarotti、Anna Checchia、Luca Crippa、Leonardo Manzoni、Carlo Scolastico

  DOI：10.1002/1099-0690(200007)2000:14<2571::aid-ejoc2571>3.0.co;2-d

  日期：2000.7

  In an effort to design dipeptide structural mimics of protein and peptide reverse-turns, a series of 5,5-, 6,5-, and 7,5-fused 2-oxo-1-azabicycloalkane amino acids has been synthesized. A new and convenient synthetic route utilizing a Horner−Emmons reaction followed by double-bond reduction has been used to prepare the bicyclic lactams in high yields.

  为了设计蛋白质和肽反转的二肽结构模拟物，合成了一系列 5,5-、6,5- 和 7,5-融合的 2-oxo-1-azabicycloalkane 氨基酸。一种利用霍纳-埃蒙斯反应和双键还原的新型便捷合成路线已被用于以高产率制备双环内酰胺。