(1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] | 635298-66-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine]
• 英文别名: tert-butyl (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-azabicyclo[2.2.1]hept-2-ene-5,2'-imidazolidine]-7-carboxylate
• CAS: 635298-66-7
• 化学式: C₂₅H₂₉N₃O₂
• 分子量: 403.524
• InChiKey: ZXVHXUPKTUDJGX-DXBBTUNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine] 在 palladium on activated charcoal 磷酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 (1R,4S)-2-氧代-7-氮杂双环[2.2.1]庚烷-7-羧酸叔丁酯
  参考文献：
  名称：

  Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: formal syntheses of natural epibatidine and its enantiomer

  摘要：

  The efficient resolution of racemic N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one (+/-)-2 via aminal formation with (R,R)-1,2-diphenylethylenediamine 4 is reported. Acidic hydrolysis furnishes the enantiomeric ketones (+)-2 and (-)-2 that were transformed into 7-azabicyclo[2.2.1]heptan-2-one (-)-3 and (+)-3. The process constitutes a formal synthesis of (+)- and (-)-epibatidine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.021
• 作为产物：
  描述：

  (1S,4R)-5-Oxo-6-(toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 (1R,4R,4'R,5'R)-4',5'-diphenylspiro[7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-5-en-2,2'-imidazolidine]
  参考文献：
  名称：

  Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: formal syntheses of natural epibatidine and its enantiomer

  摘要：

  The efficient resolution of racemic N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one (+/-)-2 via aminal formation with (R,R)-1,2-diphenylethylenediamine 4 is reported. Acidic hydrolysis furnishes the enantiomeric ketones (+)-2 and (-)-2 that were transformed into 7-azabicyclo[2.2.1]heptan-2-one (-)-3 and (+)-3. The process constitutes a formal synthesis of (+)- and (-)-epibatidine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.021

文献信息

• Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: formal syntheses of natural epibatidine and its enantiomer
  作者：Antonio J. Moreno-Vargas、Pierre Vogel

  DOI：10.1016/j.tetasy.2003.08.021

  日期：2003.10

  The efficient resolution of racemic N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one (+/-)-2 via aminal formation with (R,R)-1,2-diphenylethylenediamine 4 is reported. Acidic hydrolysis furnishes the enantiomeric ketones (+)-2 and (-)-2 that were transformed into 7-azabicyclo[2.2.1]heptan-2-one (-)-3 and (+)-3. The process constitutes a formal synthesis of (+)- and (-)-epibatidine. (C) 2003 Elsevier Ltd. All rights reserved.