9-acetyl-9-azabicyclo[3.3.1]non-2-ene-3-carbaldehyde | 1006867-22-6

• 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: 9-acetyl-9-azabicyclo[3.3.1]non-2-ene-3-carbaldehyde
• CAS: 1006867-22-6
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: PVADCRLBIKPAAB-UHFFFAOYSA-N

物化性质

• 沸点：
  367.6±42.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-acetyl-9-azabicyclo[3.3.1]non-2-ene-3-carbaldehyde 、 2-((1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)isoindoline-1,3-dione 在 titanium(IV) isopropylate 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到
  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：

  、 一氧化碳 在 palladium diacetate 三乙基硅烷 、 1,3-双(二苯基膦)丙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到9-acetyl-9-azabicyclo[3.3.1]non-2-ene-3-carbaldehyde
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives

  摘要：

  The optimization of a series of 1-aryl-3-piperidinyl urea derivatives is described in which incorporation of tropenyl and homotropenyl moieties has led to significant improvements in activity and drug-like properties. Replacement of the central piperidine with an exo-tropanyl unit led to the identification of compound 15 which provides a combination of excellent potency against human and murine receptors, drug-like properties and pharmacokinetics, thus providing a valuable tool for the evaluation of CXCR3 antagonists in models of human disease. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.109