(1R,2R,3S,5S)-3-Benzoyloxy-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester | 69610-28-2

• 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: (1R,2R,3S,5S)-3-Benzoyloxy-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester
• CAS: 69610-28-2
• 化学式: C₁₉H₂₀Cl₃NO₆
• 分子量: 464.73
• InChiKey: ATQKUZQJVKLCKX-LJISPDSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,5S)-3-Benzoyloxy-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 在 锌 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以74%的产率得到(1R,2R,3S,5S)-3-(苯甲酰氧基)-8-氮杂双环[3.2.1]辛烷-2-羧酸甲酯
  参考文献：
  名称：

  Applications of MTPA (Mosher) Amides of Secondary Amines:  Assignment of Absolute Configuration in Chiral Cyclic Amines

  摘要：

  Mosher's MTPA (methoxy(trifluoromethyl)phenylacetyl) technology is applied to the assignment of absolute configuration of several synthetic and natural chiral amines. The substrates are cyclic, secondary amines. The resulting amides usually contain significant populations of two rotamers, readily distinguished by H-1 NMR spectroscopy. Thus, two complementary sets of Delta delta values are obtained from a single analysis, thereby enhancing the power of the method. A strategy for the MTPA derivatization of (the N-methyl tertiary amine in) the tropane alkaloid, cocaine, is also described. The exceptionally large Delta delta values observed for these MTPA amides make this a valuable and reliable method for assignment of amine configuration (even in some cases where only one diastereomeric MTPA amide is readily available).

  DOI：

  10.1021/jo960373b
• 作为产物：
  描述：

  古卡因 、 氯甲酸-2,2,2-三氯乙酯 在 potassium carbonate 作用下， 以 苯 为溶剂， 反应 36.0h， 以166 mg的产率得到(1R,2R,3S,5S)-3-Benzoyloxy-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester
  参考文献：
  名称：

  Applications of MTPA (Mosher) Amides of Secondary Amines:  Assignment of Absolute Configuration in Chiral Cyclic Amines

  摘要：

  Mosher's MTPA (methoxy(trifluoromethyl)phenylacetyl) technology is applied to the assignment of absolute configuration of several synthetic and natural chiral amines. The substrates are cyclic, secondary amines. The resulting amides usually contain significant populations of two rotamers, readily distinguished by H-1 NMR spectroscopy. Thus, two complementary sets of Delta delta values are obtained from a single analysis, thereby enhancing the power of the method. A strategy for the MTPA derivatization of (the N-methyl tertiary amine in) the tropane alkaloid, cocaine, is also described. The exceptionally large Delta delta values observed for these MTPA amides make this a valuable and reliable method for assignment of amine configuration (even in some cases where only one diastereomeric MTPA amide is readily available).

  DOI：

  10.1021/jo960373b