(3S,6R,7S,10S)-methyl 2-oxo-3-N-(Boc)amino-6-nitrooxy-1-azabicyclo[5.3.0]decane-10-carboxylate | 1312682-02-2

• 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,6R,7S,10S)-methyl 2-oxo-3-N-(Boc)amino-6-nitrooxy-1-azabicyclo[5.3.0]decane-10-carboxylate
• 英文别名: methyl (3S,6S,9R,9aS)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-9-nitrooxy-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylate
• CAS: 1312682-02-2
• 化学式: C₁₆H₂₅N₃O₈
• 分子量: 387.39
• InChiKey: NIGVEKWAKLLZFT-FIQHERPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Boc-L-高烯丙基甘氨酸 在 Grubbs catalyst first generation 、 碘 、 碳酸氢钠 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 silver nitrate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.33h， 生成 (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Boc)amino-6-nitrooxy-1-azabicyclo[5.3.0]decane-10-carboxylate
  参考文献：
  名称：

  Mimics of Peptide Turn Backbone and Side-Chain Geometry by a General Approach for Modifying Azabicyclo[5.3.0]alkanone Amino Acids

  摘要：

  Peptide mimics with constrained backbone and side-chain geometry are important tools for studying structure activity relationships of biologically active candidates. A general method for creating beta-turn mimics possessing side-chain diversity has been developed featuring diastereoselective S(N)1 displacements of an iodide precursor. In particular, 6-iodo-pyrroloazepin-2-one amino ester 10 has served as a common precursor in reactions with a variety of alcohol, phenol, nitrate, and azide nucleophiles to provide an array of constrained peptide mimics.

  DOI：

  10.1021/jo2006363

文献信息

• Mimics of Peptide Turn Backbone and Side-Chain Geometry by a General Approach for Modifying Azabicyclo[5.3.0]alkanone Amino Acids
  作者：Tanya A. Godina、William D. Lubell

  DOI：10.1021/jo2006363

  日期：2011.7.15

  Peptide mimics with constrained backbone and side-chain geometry are important tools for studying structure activity relationships of biologically active candidates. A general method for creating beta-turn mimics possessing side-chain diversity has been developed featuring diastereoselective S(N)1 displacements of an iodide precursor. In particular, 6-iodo-pyrroloazepin-2-one amino ester 10 has served as a common precursor in reactions with a variety of alcohol, phenol, nitrate, and azide nucleophiles to provide an array of constrained peptide mimics.