苯乙胺,a,4-二甲基-b-苯基- | 380230-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 苯乙胺,a,4-二甲基-b-苯基-
• 英文名称: (1S,4S)-7-methyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine
• 英文别名: (1S,8R)-11-methyl-4,11-diazatricyclo[6.2.1.02,7]undeca-2(7),3,5-triene
• CAS: 380230-11-5
• 化学式: C₁₀H₁₂N₂
• 分子量: 160.219
• InChiKey: CMZQLVRJTCRKKE-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯乙胺,a,4-二甲基-b-苯基- 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 18.0h， 以151 mg的产率得到(1S,4S)-7-methyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine dihydrochloride
  参考文献：
  名称：

  Enantiospecific Synthesis of Annulated Nicotine Analogues from d-Glutamic Acid. 7-Azabicyclo[2.2.1]heptano[2.3-c]pyridines

  摘要：

  The conformationally restricted nicotinoid (1S,4S)-7-methyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine dihydrochloride has been prepared enantiospecifically from D-glutamic acid, The method involved a lithium cis-2,6-dimethylpiperidide-mediated intramolecular anionic cyclization of (2S,5R)-N-(tert-butyloxycarbonyl)-5-[3-(4-N-chloropyridinyl]proline methyl ester in tandem with a standard decarboxylation sequence. Reductive amination afforded the desired N-methylated [2.2.1]bicyclonicotinoid. Cyclization of the corresponding iodopyridinylproline methyl ester, obtained via ultrasound-facilitated chloro-iodo exchange, was also effected.

  DOI：

  10.1021/jo010534y
• 作为产物：
  描述：

  tert-butyl (1S,8R)-8-(1-oxidopyridin-1-ium-2-yl)sulfanylcarbonyl-4,11-diazatricyclo[6.2.1.02,7]undeca-2(7),3,5-triene-11-carboxylate 在 盐酸 、 sodium hydroxide 、 叔丁基硫醇 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 41.0h， 生成 苯乙胺,a,4-二甲基-b-苯基-
  参考文献：
  名称：

  Enantiospecific Synthesis of Annulated Nicotine Analogues from d-Glutamic Acid. 7-Azabicyclo[2.2.1]heptano[2.3-c]pyridines

  摘要：

  The conformationally restricted nicotinoid (1S,4S)-7-methyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine dihydrochloride has been prepared enantiospecifically from D-glutamic acid, The method involved a lithium cis-2,6-dimethylpiperidide-mediated intramolecular anionic cyclization of (2S,5R)-N-(tert-butyloxycarbonyl)-5-[3-(4-N-chloropyridinyl]proline methyl ester in tandem with a standard decarboxylation sequence. Reductive amination afforded the desired N-methylated [2.2.1]bicyclonicotinoid. Cyclization of the corresponding iodopyridinylproline methyl ester, obtained via ultrasound-facilitated chloro-iodo exchange, was also effected.

  DOI：

  10.1021/jo010534y

文献信息

• Enantiospecific Synthesis of Annulated Nicotine Analogues from <scp>d</scp>-Glutamic Acid. 7-Azabicyclo[2.2.1]heptano[2.3-<i>c</i>]pyridines
  作者：Joseph R. Lennox、Sean C. Turner、Henry Rapoport

  DOI：10.1021/jo010534y

  日期：2001.10.1

  The conformationally restricted nicotinoid (1S,4S)-7-methyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine dihydrochloride has been prepared enantiospecifically from D-glutamic acid, The method involved a lithium cis-2,6-dimethylpiperidide-mediated intramolecular anionic cyclization of (2S,5R)-N-(tert-butyloxycarbonyl)-5-[3-(4-N-chloropyridinyl]proline methyl ester in tandem with a standard decarboxylation sequence. Reductive amination afforded the desired N-methylated [2.2.1]bicyclonicotinoid. Cyclization of the corresponding iodopyridinylproline methyl ester, obtained via ultrasound-facilitated chloro-iodo exchange, was also effected.