(Z)-5-<<5-(4-Methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-<<5-(4-Methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoic acid
• 英文别名: (Z)-5-{[5-(4-Methoxyphenyl)-4-pentenyl]amino}-5-oxopentanoic acid；5-[[(Z)-5-(4-methoxyphenyl)pent-4-enyl]amino]-5-oxopentanoic acid
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: UIXOWAPDRDNDRN-UTCJRWHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-5-<<5-(4-Methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoic acid 在 六甲基二硅氧烷 、 phosphorus pentoxide 、 N,N-二异丙基乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-Ethyl 4-<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
• 作为产物：
  描述：

  (Z)-2-<5-(4-Methoxyphenyl)-4-pentenyl>-1H-isoindole-1,3(2H)-dione 在 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (Z)-5-<<5-(4-Methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoic acid
  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

文献信息

• Synthesis of Chiral Hydroxylated Quinolizidines via Vinylogous Bischler-Napieralski Nitrilium Ion Cyclizations
  作者：Angela L. Marquart、Brent L. Podlogar、Edward W. Huber、David A. Demeter、Norton P. Peet、Herschel J. R. Weintraub、Michael R. Angelastro

  DOI：10.1021/jo00087a026

  日期：1994.4

  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.