(1R,3R,5S)-3-Methoxycarbonylmethyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester | 548458-95-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (1R,3R,5S)-3-Methoxycarbonylmethyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester
• CAS: 548458-95-3
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: CJPWBROLBXLZAM-JGPRNRPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,5S)-3-Methoxycarbonylmethyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-{2-[bis-(4-fluorophenyl)methoxy]ethyl}-8-methyl-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis of dopamine transporter selective 3-{2-(Diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo[3.2.1]octanes

  摘要：

  A series of 3-{2-(diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo[3.2.1]octanes was synthesized and the binding affinities of the compounds were determined at the dopamine and serotonin transporters. The 8-phenylpropyl analogues 8a (K-i = 4.1 nM) and 8b (K-i = 3.7 nM) were the most potent compounds of the series with binding affinities 3 times greater than GBR12909. In addition, 8a (SERT DAT 327) was over 300-fold more selective for the dopamine transporter than the serotonin transporter. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01051-x
• 作为产物：
  描述：

  8-ethoxycarbonyl-3-methoxycarbomethylidenyl-8-azabicyclo[3.2.1]octane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到(1R,3R,5S)-3-Methoxycarbonylmethyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of dopamine transporter selective 3-{2-(Diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo[3.2.1]octanes

  摘要：

  A series of 3-{2-(diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo[3.2.1]octanes was synthesized and the binding affinities of the compounds were determined at the dopamine and serotonin transporters. The 8-phenylpropyl analogues 8a (K-i = 4.1 nM) and 8b (K-i = 3.7 nM) were the most potent compounds of the series with binding affinities 3 times greater than GBR12909. In addition, 8a (SERT DAT 327) was over 300-fold more selective for the dopamine transporter than the serotonin transporter. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01051-x