methyl (1R,2R,5S)-8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl (1R,2R,5S)-8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: XNWMGKAGYXRTAI-GZBFAFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1R,2R,5S)-8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 生成 methyl (1R,2R,5S)-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate
  参考文献：
  名称：

  Novel asymmetric dealkoxycarbonylation of 3-oxo-8-azabicyclo[3.2.1]-octane-2,4-dicar☐ylates using porcine liver esterase: A new route to (−)-anhydroecgonine methyl ester

  摘要：

  The porcine liver esterase-catalyzed dealkoxycarbonylation of 8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylates (4) was found to give high enantiomeric excess of the desymmetrized keto ester (5). This novel dealkoxylcarbonylation opened a new route to the asymmetric synthesis of (1R)cocaine related radiopharmaceuticals such as (1R)-beta-CIT, for diagnosis of Parkinson's disease. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00976-4
• 作为产物：
  描述：

  diisopropyl 8-benzyl-3-oxo-8-azabicyclo[3.2.1]-octane-2,4-dicarboxylate 在 porcine liver esterase 、 phosphate buffer 、 sodium 作用下， 以 水 为溶剂， 反应 24.0h， 生成 methyl (1R,2R,5S)-8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate
  参考文献：
  名称：

  Novel asymmetric dealkoxycarbonylation of 3-oxo-8-azabicyclo[3.2.1]-octane-2,4-dicar☐ylates using porcine liver esterase: A new route to (−)-anhydroecgonine methyl ester

  摘要：

  The porcine liver esterase-catalyzed dealkoxycarbonylation of 8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylates (4) was found to give high enantiomeric excess of the desymmetrized keto ester (5). This novel dealkoxylcarbonylation opened a new route to the asymmetric synthesis of (1R)cocaine related radiopharmaceuticals such as (1R)-beta-CIT, for diagnosis of Parkinson's disease. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00976-4

文献信息

• Novel asymmetric dealkoxycarbonylation of 3-oxo-8-azabicyclo[3.2.1]-octane-2,4-dicar☐ylates using porcine liver esterase: A new route to (−)-anhydroecgonine methyl ester
  作者：Manabu Node、Soichi Nakamura、Daisaku Nakamura、Takahiro Katoh、Kiyoharu Nishide

  DOI：10.1016/s0040-4039(99)00976-4

  日期：1999.7

  The porcine liver esterase-catalyzed dealkoxycarbonylation of 8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylates (4) was found to give high enantiomeric excess of the desymmetrized keto ester (5). This novel dealkoxylcarbonylation opened a new route to the asymmetric synthesis of (1R)cocaine related radiopharmaceuticals such as (1R)-beta-CIT, for diagnosis of Parkinson's disease. (C) 1999 Elsevier Science Ltd. All rights reserved.