(1S)-[2-(tert-butyldimethylsiloxy)-1-(4-methoxybenzyl)ethyl]-N-[8-(1-methoxypropa-1,2-dienyl)-1,4-dithiaspiro[4.5]dec-8-yl]amine | 915027-01-9

• 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: (1S)-[2-(tert-butyldimethylsiloxy)-1-(4-methoxybenzyl)ethyl]-N-[8-(1-methoxypropa-1,2-dienyl)-1,4-dithiaspiro[4.5]dec-8-yl]amine
• CAS: 915027-01-9
• 化学式: C₂₈H₄₅NO₃S₂Si
• 分子量: 535.888
• InChiKey: PGAKFUMURLBGTA-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.02
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  90.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S)-[2-(tert-butyldimethylsiloxy)-1-(4-methoxybenzyl)ethyl]-N-[8-(1-methoxypropa-1,2-dienyl)-1,4-dithiaspiro[4.5]dec-8-yl]amine 在 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 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 28.3h， 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
• 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 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 69.25h， 生成 (1S)-[2-(tert-butyldimethylsiloxy)-1-(4-methoxybenzyl)ethyl]-N-[8-(1-methoxypropa-1,2-dienyl)-1,4-dithiaspiro[4.5]dec-8-yl]amine
  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.