3-phenethyl-8-β-amino-3-azabicyclo<3.2.1>octan-8-α-carbonitrile | 138043-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-phenethyl-8-β-amino-3-azabicyclo<3.2.1>octan-8-α-carbonitrile
• CAS: 138043-00-2
• 化学式: C₁₆H₂₁N₃
• 分子量: 255.363
• InChiKey: UQCNLKNYIDJTER-ZSHCYNCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  53.05
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  氰化钾 、 3-phenethyl-3-azabicyclo<3.2.1>octan-8-one 在 ammonium chloride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 576.0h， 以5%的产率得到3-phenethyl-8-β-amino-3-azabicyclo<3.2.1>octan-8-α-carbonitrile
  参考文献：
  名称：

  Synthesis and structural and conformational study of some esters derived from 8-β-hydroxy-3-phenethyl-3- azabicyclico [3.2.11] octan-8-α-carboxylic acid

  摘要：

  A series of 8-beta-hydroxy-8-alpha-alkoxycarbonyl-N-phenethyl-3-azabicyclo[3.2.1]octane derivatives have been synthesized and studied by IR, H-1 and C-13 NMR spectroscopy, and the crystal structure of ethyl-8-beta-hydroxy-3-phenethyl-3-azabicyclo[3.2.1]octan-8-alpha-carboxylate (Va) has been determined by X-ray diffraction. In deuterochloroform and deuterobenzene the cyclopentane and piperidine rings of the title compounds shown an envelope conformation flattened at C8 and a distorted chair conformation puckered at C8 and flattened at N3, respectively, with the N-substituent in an equatorial position. These results are in close agreement with that found for compound Va in the crystalline state. By comparing the NMR and X-ray parameters of the title compounds with those of the corresponding 8-alpha-hydroxy-8-beta-alkoxycarbonyl-N-phenethyl-3-azabicyclo[3.2.1]octane epimers and 3-phenethyl-3-azabicyclo[3.2.1]octan-8-alpha-(and betol, several stereoelectronic effects have been deduced.

  DOI：

  10.1016/0022-2860(91)85068-e