-Tetrahydro-N-<5-(4-methoxyphenyl)-4-pentenyl>-5-oxo-2-furancarboxamide | 1025893-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: -Tetrahydro-N-<5-(4-methoxyphenyl)-4-pentenyl>-5-oxo-2-furancarboxamide
• 英文别名: (2S)-N-[(Z)-5-(4-methoxyphenyl)pent-4-enyl]-5-oxooxolane-2-carboxamide
• CAS: 1025893-00-8
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: OGGDLHDCABIXOX-QTLSWZBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  -Tetrahydro-N-<5-(4-methoxyphenyl)-4-pentenyl>-5-oxo-2-furancarboxamide 在 六甲基二硅氧烷 、 sodium ethanolate 、 phosphorus pentoxide 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 72.5h， 生成 [(1S)-4-ethoxy-1-[(5E)-5-[(4-methoxyphenyl)methylidene]-3,4-dihydro-2H-pyridin-6-yl]-4-oxobutyl] benzoate
  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：

  (S)-(+)-5-氧代-2-四氢呋喃羧酸 在 氯化亚砜 、 TEA 作用下， 以 二氯甲烷 为溶剂， 生成 -Tetrahydro-N-<5-(4-methoxyphenyl)-4-pentenyl>-5-oxo-2-furancarboxamide
  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.