1-methyl-2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-methyl-2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
• 英文别名: (1S,2R,4R,5R)-2,4-bis(4-methoxyphenyl)-1-methyl-3-azabicyclo[3.3.1]nonan-9-one
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: OHLFQYILFQZWMO-SRUXOGRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one 在 盐酸 、 sodium nitrite 作用下， 以 氯仿 、 水 为溶剂， 反应 1.0h， 生成 N-nitroso-1-methyl-2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
  参考文献：
  名称：

  Spontaneous generation of chirality and chiroptical spectra of N-nitroso-2,4-diaryl-3-azabicyclo[3.3.1]nonanes

  摘要：

  The crystal structures of several bicyclic N-nitrosamines indicate that they crystallize in the chiral (Sohncke) space group P2(1)2(1)2(1) as conglomerates. This allows the resolution of these compounds by manual picking of the enantiomorphous crystals. The optical activity of the single crystals was confirmed by their CD spectra taken in KBr disks. The absolute configurations of the title nitrosamines were assigned by crystallographic measurements and by a comparison of their CD spectra with those of a reference compound resolved by classical methods. The observed Cotton effect signs, corresponding to the n-pi* transition, were correlated with the helicity of the inherently chiral nitrosamine chromophore. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.02.012
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 2-甲基环己酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以61%的产率得到1-methyl-2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
  参考文献：
  名称：

  Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents

  摘要：

  Libraries of 1-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/O-methyloximes 1-14/15-28/29-42 and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/O-methyloximes 43-48/49-54/55-60 were synthesized and their stereochemistry was established by 1D/2D NMR spectral and single crystal XRD studies. All the synthesized oximes and oxime ethers were screened for their in vitro antimicrobial activity against a panel of pathogenic bacteria (Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumoniae and Pseudomonas aeruginosa) and fungi (Candida albicans, Candida parapsilosis, Aspergillus niger and Cryptococcus neoformans) using Gentamicin and Fluconazole as standards, respectively. From the SAR profile, the lead molecules were identified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.048