1-(3-(((1R,3s,5S)-3-amino-8-azabicyclo[3.2.1]octan-8-yl)methyl)-9-azabicyclo[3.3.1]non-2-en-9-yl)ethan-1-one | 1011533-41-7

• 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: 1-(3-(((1R,3s,5S)-3-amino-8-azabicyclo[3.2.1]octan-8-yl)methyl)-9-azabicyclo[3.3.1]non-2-en-9-yl)ethan-1-one
• CAS: 1011533-41-7
• 化学式: C₁₈H₂₉N₃O
• 分子量: 303.448
• InChiKey: VQYARGLPJUKHBD-QBXJUSAXSA-N

物化性质

• 沸点：
  459.3±45.0 °C(predicted)
• 密度：
  1.125±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.57
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(3-(((1R,3s,5S)-3-amino-8-azabicyclo[3.2.1]octan-8-yl)methyl)-9-azabicyclo[3.3.1]non-2-en-9-yl)ethan-1-one 、 2-氯-6-三氟甲基喹啉 在 sodium t-butanolate 、 2-(二环己基膦基)联苯 作用下， 以 N-甲基吡咯烷酮 、 甲苯 为溶剂， 生成 1-(3-(((1R,3s,5S)-3-((6-(trifluoromethyl)quinolin-2-yl)amino)-8-azabicyclo[3.2.1]octan-8-yl)methyl)-9-azabicyclo[3.3.1]non-2-en-9-yl)ethan-1-one
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 4: Discovery of 2-amino-(4-tropinyl)quinolines

  摘要：

  The synthesis and biological evaluation of a novel series of 2-aminoquinoline substituted piperidines and tropanes incorporating a homotropene moiety is herein described. The series exhibits potent antagonism of the CXCR3 receptor and superior physicochemical properties. Compound 24d was found to be orally bioavailable, and PK/PD studies suggested it as a suitable tool for studying the role of CXCR3 in models of disease. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.075
• 作为产物：
  描述：

  在 肼 作用下， 以 乙醇 为溶剂， 以81%的产率得到1-(3-(((1R,3s,5S)-3-amino-8-azabicyclo[3.2.1]octan-8-yl)methyl)-9-azabicyclo[3.3.1]non-2-en-9-yl)ethan-1-one
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 4: Discovery of 2-amino-(4-tropinyl)quinolines

  摘要：

  The synthesis and biological evaluation of a novel series of 2-aminoquinoline substituted piperidines and tropanes incorporating a homotropene moiety is herein described. The series exhibits potent antagonism of the CXCR3 receptor and superior physicochemical properties. Compound 24d was found to be orally bioavailable, and PK/PD studies suggested it as a suitable tool for studying the role of CXCR3 in models of disease. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.075