(1R,4S)-7-tert-butyloxycarbonyl-1-methoxycarbonyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine | 378791-82-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,4S)-7-tert-butyloxycarbonyl-1-methoxycarbonyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine
• 英文别名: 11-O-tert-butyl 8-O-methyl (1S,8R)-4,11-diazatricyclo[6.2.1.02,7]undeca-2(7),3,5-triene-8,11-dicarboxylate
• CAS: 378791-82-3
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: GBHPZZCBBQHHCU-BLLLJJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,4S)-7-tert-butyloxycarbonyl-1-methoxycarbonyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine 在 吡啶 、 盐酸 、 lithium hydroxide 、 sodium hydroxide 、 草酰氯 、 叔丁基硫醇 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 55.0h， 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
• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-(2R,5S)-5-[3-(4'-chloropyridinyl)]proline methyl ester 在 正丁基锂 、 (2R,6S)-2,6-dimethylpiperidine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以57%的产率得到(1R,4S)-7-tert-butyloxycarbonyl-1-methoxycarbonyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine
  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