6-(1-methoxy-2-phenylpropenyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

• 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 benzyl ester
• 英文别名: benzyl 6-[(E)-1-methoxy-2-phenylprop-1-enyl]-3,4-dihydro-2H-pyridine-1-carboxylate
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.456
• InChiKey: ACEAOKWMFXYXIQ-RELWKKBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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 benzyl ester 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以78%的产率得到1-methoxy-1-(1phenylethyl)-1,5,6,7-tetrahydrooxazolo[3,4-a]pyridin-3-one
  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：

  6-trifluoroomethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 、 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 18.0h， 以64%的产率得到6-(1-methoxy-2-phenylpropenyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl 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

文献信息

• Synthesis of α-Acyl-Functionalized Azacycles by Pd-Catalyzed Cross-Coupling Reactions of α-Alkoxyboronates with Lactam-Derived Vinyl Triflates
  作者：Ernesto G. Occhiato、Cristina Prandi、Alessandro Ferrali、Antonio Guarna、Annamaria Deagostino、Paolo Venturello

  DOI：10.1021/jo025930a

  日期：2002.10.1

  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.