(1R,7R,9R)-7-(3-aminophenyl)-2-oxo-8,10-dioxa-3-azabicyclo[5.2.1]decane-9-carboxylic acid dimethyl ester | 878790-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,7R,9R)-7-(3-aminophenyl)-2-oxo-8,10-dioxa-3-azabicyclo[5.2.1]decane-9-carboxylic acid dimethyl ester
• 英文别名: methyl (1R,7R,9R)-7-(3-aminophenyl)-2-oxo-8,10-dioxa-3-azabicyclo[5.2.1]decane-9-carboxylate
• CAS: 878790-18-2
• 化学式: C₁₅H₁₈N₂O₅
• 分子量: 306.318
• InChiKey: BIKARBGGFTVDBO-LALPHHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,7R,9R)-7-(3-aminophenyl)-2-oxo-8,10-dioxa-3-azabicyclo[5.2.1]decane-9-carboxylic acid dimethyl ester 在 lithium hydroxide 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 24.5h， 生成 (1R,2S,7R,9R)-7-{3-[2-(9H-fluoren-9-yl-methoxycarbonylamino)propionylamino]phenyl}-2-oxo-8,10-dioxa-3-azabicyclo[5.2.1]decane-9-carboxylic acid
  参考文献：
  名称：

  3-Aza-8,10-dioxa-bicyclo[5.2.1]decane (9-exo BTKa) carboxylic acid as a new reverse turn inducer: synthesis and conformational analysis of a model peptide

  摘要：

  Dipeptide isostere 5, belonging to the class of 9-exo BTKa, was synthesised starting from R,R-tartaric acid and 4-nitro-1-(3-nitrophenyl)butan-1-one. The nine-membered lactam showed interesting structural features and was inserted in a 5-residue model peptide. The conformational properties of this modified peptide have been Studied by NMR and molecular modelling, indicating that Compound 5 acted as it reverse turn inducer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.008
• 作为产物：
  描述：

  (4R,5R)-2-(3-nitrophenyl)-2-(3-nitropropyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以40%的产率得到(1R,7R,9R)-7-(3-aminophenyl)-2-oxo-8,10-dioxa-3-azabicyclo[5.2.1]decane-9-carboxylic acid dimethyl ester
  参考文献：
  名称：

  3-Aza-8,10-dioxa-bicyclo[5.2.1]decane (9-exo BTKa) carboxylic acid as a new reverse turn inducer: synthesis and conformational analysis of a model peptide

  摘要：

  Dipeptide isostere 5, belonging to the class of 9-exo BTKa, was synthesised starting from R,R-tartaric acid and 4-nitro-1-(3-nitrophenyl)butan-1-one. The nine-membered lactam showed interesting structural features and was inserted in a 5-residue model peptide. The conformational properties of this modified peptide have been Studied by NMR and molecular modelling, indicating that Compound 5 acted as it reverse turn inducer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.008