methyl (1S,4R,5R)-2-[(1S,4R,5R)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[2.1.1]hexane-5-carbonyl]-2-azabicyclo[2.1.1]hexane-5-carboxylate | 1256914-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (1S,4R,5R)-2-[(1S,4R,5R)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[2.1.1]hexane-5-carbonyl]-2-azabicyclo[2.1.1]hexane-5-carboxylate
• CAS: 1256914-31-4
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: GQSHVPRXGFPLNP-SNIKSBKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1S,4R,5R)-2-[(1S,4R,5R)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[2.1.1]hexane-5-carbonyl]-2-azabicyclo[2.1.1]hexane-5-carboxylate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (1S,4R,5R)-2-((1S,4R,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-5-carbonyl)-2-azabicyclo[2.1.1]hexane-5-carboxylic acid
  参考文献：
  名称：

  Oligomers of a 5-Carboxy-methanopyrrolidine β-Amino Acid. A Search for Order

  摘要：

  CD spectra for homooligomers (n = 4, 6, 8) of (1S,4R,5R)-5-syn-carboxy-2-azabicyclo[2.1.1]hexane (MPCA), a methano-bridged pyrrolidine beta-carboxylic acid, suggest an ordered secondary structure. Even in the absence of internal hydrogen bonding, solution NMR, X-ray, and in silico analyses of the tetramer are indicative of conformations with trans-amides and C-5-amide-carbonyls oriented toward the C-4 bridgehead This highly constrained beta-amino acid could prove useful in the ongoing development of well-defined foldamers.

  DOI：

  10.1021/ol1022917
• 作为产物：
  描述：

  syn-N-(t-butoxycarbonyl)-5-carboxy-2-azabicyclo[2.1.1]hexane 、 (1S, 4R, 5R)-(-)-5-syn-methoxycarbonyl-N-Boc-2-azabicyclo[2.1.1]hexane 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 以34%的产率得到methyl (1S,4R,5R)-2-[(1S,4R,5R)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[2.1.1]hexane-5-carbonyl]-2-azabicyclo[2.1.1]hexane-5-carboxylate
  参考文献：
  名称：

  Oligomers of a 5-Carboxy-methanopyrrolidine β-Amino Acid. A Search for Order

  摘要：

  CD spectra for homooligomers (n = 4, 6, 8) of (1S,4R,5R)-5-syn-carboxy-2-azabicyclo[2.1.1]hexane (MPCA), a methano-bridged pyrrolidine beta-carboxylic acid, suggest an ordered secondary structure. Even in the absence of internal hydrogen bonding, solution NMR, X-ray, and in silico analyses of the tetramer are indicative of conformations with trans-amides and C-5-amide-carbonyls oriented toward the C-4 bridgehead This highly constrained beta-amino acid could prove useful in the ongoing development of well-defined foldamers.

  DOI：

  10.1021/ol1022917