-Ethyl 4-<2-(benzoyloxy)-3,4,5,6-tetrahydro-3-<(4-methoxyphenyl)methylene>-2-pyridinyl>butanoate | 155768-51-7

• 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: -Ethyl 4-<2-(benzoyloxy)-3,4,5,6-tetrahydro-3-<(4-methoxyphenyl)methylene>-2-pyridinyl>butanoate
• 英文别名: [(2S)-1-ethoxy-4-[(5E)-5-[(4-methoxyphenyl)methylidene]-3,4-dihydro-2H-pyridin-6-yl]-1-oxobutan-2-yl] benzoate
• CAS: 155768-51-7
• 化学式: C₂₆H₂₉NO₅
• 分子量: 435.52
• InChiKey: ZTMIXEYXRMZYCA-XGMDJLNPSA-N

物化性质

• 沸点：
  597.5±50.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  -Ethyl 4-<2-(benzoyloxy)-3,4,5,6-tetrahydro-3-<(4-methoxyphenyl)methylene>-2-pyridinyl>butanoate 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 dimethyl sulfide borane 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.5h， 生成 <1S-(1α,7α,9a-β)>-Octahydro-2H-quinolizine-1,7-diol
  参考文献：
  名称：

  Synthesis of Chiral Hydroxylated Quinolizidines via Vinylogous Bischler-Napieralski Nitrilium Ion Cyclizations

  摘要：

  Treatment of the amido esters 9 and 17 with PPSE (polyphosphoric acid trimethylsilyl ester) followed by NaBH4 in ethanol gave the quinolizidinones 11-14 and 19 via a vinylogous Bischler-Napieralski nitrilium ion cyclization-reductive lactamization two-step process. Subsequent ozonolysis and reduction afforded chiral hydroxylated quinolizidines in moderate to good yield. In contrast to five-membered-ring formation, six-membered-ring formation via nitrilium-ion cyclization requires a p-methoxy-substituted styryl terminator. The effect para-substituted styryl terminators have on the energy of activation and Delta H for the cyclization process has been calculated by semiempirical and ab initio methods.

  DOI：

  10.1021/jo00087a026
• 作为产物：
  描述：

  -Ethyl 2-hydroxy-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate 在 六甲基二硅氧烷 、 phosphorus pentoxide 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 -Ethyl 4-<2-(benzoyloxy)-3,4,5,6-tetrahydro-3-<(4-methoxyphenyl)methylene>-2-pyridinyl>butanoate
  参考文献：
  名称：

  Synthesis of Chiral Hydroxylated Quinolizidines via Vinylogous Bischler-Napieralski Nitrilium Ion Cyclizations

  摘要：

  Treatment of the amido esters 9 and 17 with PPSE (polyphosphoric acid trimethylsilyl ester) followed by NaBH4 in ethanol gave the quinolizidinones 11-14 and 19 via a vinylogous Bischler-Napieralski nitrilium ion cyclization-reductive lactamization two-step process. Subsequent ozonolysis and reduction afforded chiral hydroxylated quinolizidines in moderate to good yield. In contrast to five-membered-ring formation, six-membered-ring formation via nitrilium-ion cyclization requires a p-methoxy-substituted styryl terminator. The effect para-substituted styryl terminators have on the energy of activation and Delta H for the cyclization process has been calculated by semiempirical and ab initio methods.

  DOI：

  10.1021/jo00087a026