Benzoic acid (R)-1-methoxycarbonyl-3-{3-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-3,4,5,6-tetrahydro-pyridin-2-yl}-propyl ester | 1026409-96-0

• 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: Benzoic acid (R)-1-methoxycarbonyl-3-{3-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-3,4,5,6-tetrahydro-pyridin-2-yl}-propyl ester
• 英文别名: [(2R)-1-methoxy-4-[(5E)-5-[(4-methoxyphenyl)methylidene]-3,4-dihydro-2H-pyridin-6-yl]-1-oxobutan-2-yl] benzoate
• CAS: 1026409-96-0
• 化学式: C₂₅H₂₇NO₅
• 分子量: 421.493
• InChiKey: JPSKUZFCAPIWIJ-VEYZUFFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  Benzoic acid (R)-1-methoxycarbonyl-3-{3-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-3,4,5,6-tetrahydro-pyridin-2-yl}-propyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 <3R-(3β,9E,9a-α)>-3-(Benzoyloxy)octahydro-9-<(4-methoxyphenyl)methylene>-4H-quinolizin-4-one 、 <3R-(3β,9E,9a-β)>-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 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 139.0h， 生成 Benzoic acid (R)-1-methoxycarbonyl-3-{3-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-3,4,5,6-tetrahydro-pyridin-2-yl}-propyl ester
  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.