-Ethyl 2-(benzoyloxy)-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate | 155768-49-3

• 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 2-(benzoyloxy)-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate
• 英文别名: [(2S)-1-ethoxy-5-[[(Z)-5-(4-methoxyphenyl)pent-4-enyl]amino]-1,5-dioxopentan-2-yl] benzoate
• CAS: 155768-49-3
• 化学式: C₂₆H₃₁NO₆
• 分子量: 453.535
• InChiKey: QWVIOSMMDJESCG-ZJZKVMBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  -Ethyl 2-(benzoyloxy)-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate 在 sodium tetrahydroborate 、 六甲基二硅氧烷 、 phosphorus pentoxide 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 3.0h， 生成 <3S-(3α,9E,9a-α)>-3-(Benzoyloxy)octahydro-9-<(4-methoxyphenyl)methylene>-4H-quinolizin-4-one
  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：

  (Z)-5-(4-Methoxyphenyl)-4-penten-1-amine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 138.0h， 生成 -Ethyl 2-(benzoyloxy)-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate
  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