(5S,6R,7R,11S)-6-hydroxy-1-methoxy-5-(4-methoxybenzyl)-6,7,9,10-tetrahydro-3H-7,10a-methanopyrrolo[1,2-a]azocine-8(5H)-one | 915027-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5S,6R,7R,11S)-6-hydroxy-1-methoxy-5-(4-methoxybenzyl)-6,7,9,10-tetrahydro-3H-7,10a-methanopyrrolo[1,2-a]azocine-8(5H)-one
• 英文别名: (1S,6S,7R,8R)-7-hydroxy-2-methoxy-6-[(4-methoxyphenyl)methyl]-5-azatricyclo[6.3.1.01,5]dodec-2-en-9-one
• CAS: 915027-11-1
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: WTFBQUOARCFLNY-FEHORTKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S,6R,7R,11S)-6-hydroxy-1-methoxy-5-(4-methoxybenzyl)-6,7,9,10-tetrahydro-3H-7,10a-methanopyrrolo[1,2-a]azocine-8(5H)-one 、 cesium acetate 在 4-二甲氨基吡啶 、 三乙胺 、 对硝基苯磺酰氯 、 18-冠醚-6 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以50%的产率得到(5S,6R,7S,11S)-6-chloro-1-methoxy-5-(4-methoxybenzyl)-6,7,9,10-tetrahydro-3H-7,10a-methanopyrrolo[1,2-a]azocine-8(5H)-one
  参考文献：
  名称：

  Efficient Approach to the Azaspirane Core of FR 901483

  摘要：

  An efficient approach to the azaspirane core of FR 901483 is described employing lithiated methoxyallene as a crucial C3 building block and a suitably protected enantiopure ketimine as the second component. The resulting dihydropyrrole derivative was smoothly converted into a spiro keto aldehyde which under acidic conditions provided a novel azanorbornane derivative 15. Under basic reaction conditions, the desired 5-azatricyclo[6.3.1.0(1,5)] dodecane skeleton 16 was generated. The ratio of diastereomers strongly depends on the reaction conditions employed with L-proline in DMSO providing the highest selectivity in favor of one azaspirane product.

  DOI：

  10.1021/ol061538y
• 作为产物：
  描述：

  (S)-2-amino-3-(4-methoxyphenyl)propan-1-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 pyridine-SO3 complex 、 四丁基氟化铵 、 potassium carbonate 、 silver nitrate 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 、 L-脯氨酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 97.55h， 生成 (5S,6R,7R,11S)-6-hydroxy-1-methoxy-5-(4-methoxybenzyl)-6,7,9,10-tetrahydro-3H-7,10a-methanopyrrolo[1,2-a]azocine-8(5H)-one
  参考文献：
  名称：

  Efficient Approach to the Azaspirane Core of FR 901483

  摘要：

  An efficient approach to the azaspirane core of FR 901483 is described employing lithiated methoxyallene as a crucial C3 building block and a suitably protected enantiopure ketimine as the second component. The resulting dihydropyrrole derivative was smoothly converted into a spiro keto aldehyde which under acidic conditions provided a novel azanorbornane derivative 15. Under basic reaction conditions, the desired 5-azatricyclo[6.3.1.0(1,5)] dodecane skeleton 16 was generated. The ratio of diastereomers strongly depends on the reaction conditions employed with L-proline in DMSO providing the highest selectivity in favor of one azaspirane product.

  DOI：

  10.1021/ol061538y

文献信息

• Efficient Approach to the Azaspirane Core of FR 901483
  作者：Silvia Kaden、Hans-Ulrich Reissig

  DOI：10.1021/ol061538y

  日期：2006.10.1

  An efficient approach to the azaspirane core of FR 901483 is described employing lithiated methoxyallene as a crucial C3 building block and a suitably protected enantiopure ketimine as the second component. The resulting dihydropyrrole derivative was smoothly converted into a spiro keto aldehyde which under acidic conditions provided a novel azanorbornane derivative 15. Under basic reaction conditions, the desired 5-azatricyclo[6.3.1.0(1,5)] dodecane skeleton 16 was generated. The ratio of diastereomers strongly depends on the reaction conditions employed with L-proline in DMSO providing the highest selectivity in favor of one azaspirane product.