6-(1-methoxy-2-phenylpropenyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester | 473895-22-6

• 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: 6-(1-methoxy-2-phenylpropenyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester
• 英文别名: methyl 6-[(E)-1-methoxy-2-phenylprop-1-enyl]-3,4-dihydro-2H-pyridine-1-carboxylate
• CAS: 473895-22-6
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: KZHFQFONRQIQOS-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(1-methoxy-2-phenylpropenyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester 在 Amberlyst 15 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以93%的产率得到6-(2-phenylpropionyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of α-Acyl-Functionalized Azacycles by Pd-Catalyzed Cross-Coupling Reactions of α-Alkoxyboronates with Lactam-Derived Vinyl Triflates

  摘要：

  Alkoxydienyl- and alkoxystyrylboronates were used for Pd-catalyzed cross-coupling reactions with lactam-derived vinyl triflates. The hydrolysis of the coupling products with alkoxystyrylboronates provided the corresponding (x-acyl-substituted 3,4-dihydro-(2H)-pyridines and 2,3,4,5-tetrahydroazepines in good to high yields. The hydrolysis of the coupling products with alkoxydienylboronates, performed in the presence of Amberlyst 15, resulted in a Nazarov-type cyclization that afforded hexahydro[1]pyrindin-7-ones and 3,4,5,6,7,8-hexahydro-(2H)-cyclopenta[b]azepin-8-ones. This methodology represents a novel and efficient procedure for the preparation of these classes of azacyclic compounds.

  DOI：

  10.1021/jo025930a
• 作为产物：
  描述：

  methyl 6-(trifluoromethylsulfonyloxy)-1,2,3,4-tetrahydropyridine-1-carboxylate 、 2-[(E)-1-methoxy-2-phenylprop-1-enyl]-5,5-dimethyl-1,3,2-dioxaborinane 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 以68%的产率得到6-(1-methoxy-2-phenylpropenyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of α-Acyl-Functionalized Azacycles by Pd-Catalyzed Cross-Coupling Reactions of α-Alkoxyboronates with Lactam-Derived Vinyl Triflates

  摘要：

  Alkoxydienyl- and alkoxystyrylboronates were used for Pd-catalyzed cross-coupling reactions with lactam-derived vinyl triflates. The hydrolysis of the coupling products with alkoxystyrylboronates provided the corresponding (x-acyl-substituted 3,4-dihydro-(2H)-pyridines and 2,3,4,5-tetrahydroazepines in good to high yields. The hydrolysis of the coupling products with alkoxydienylboronates, performed in the presence of Amberlyst 15, resulted in a Nazarov-type cyclization that afforded hexahydro[1]pyrindin-7-ones and 3,4,5,6,7,8-hexahydro-(2H)-cyclopenta[b]azepin-8-ones. This methodology represents a novel and efficient procedure for the preparation of these classes of azacyclic compounds.

  DOI：

  10.1021/jo025930a