(S)-2-(4-methoxy-8-oxo-1-azaspiro[4.5]dec-3-en-1-yl)-3-(4-methoxyphenyl)propanal | 915027-03-1

• 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: (S)-2-(4-methoxy-8-oxo-1-azaspiro[4.5]dec-3-en-1-yl)-3-(4-methoxyphenyl)propanal
• 英文别名: (2S)-2-(4-methoxy-8-oxo-1-azaspiro[4.5]dec-3-en-1-yl)-3-(4-methoxyphenyl)propanal
• CAS: 915027-03-1
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: VBZZSTPBXKILEA-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-methoxy-8-oxo-1-azaspiro[4.5]dec-3-en-1-yl)-3-(4-methoxyphenyl)propanal 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 三乙胺 、 对硝基苯磺酰氯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (5S,6R,7R,11S)-1-methoxy-5-(4-methoxybenzyl)-8-oxo-5,6,7,9,10-pentahydro-3H-7,10a-methanopyrrolo[1,2-a]azocine-6-ylacetate
  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 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 83.55h， 生成 (S)-2-(4-methoxy-8-oxo-1-azaspiro[4.5]dec-3-en-1-yl)-3-(4-methoxyphenyl)propanal
  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.