dimethyl 1-(4-chlorobenzyl)-4,6,6-triphenyl-1,6-dihydropyridine-2,3-dicarboxylate | 1450999-78-6

• 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: dimethyl 1-(4-chlorobenzyl)-4,6,6-triphenyl-1,6-dihydropyridine-2,3-dicarboxylate
• 英文别名: Dimethyl 1-[(4-chlorophenyl)methyl]-4,6,6-triphenylpyridine-2,3-dicarboxylate；dimethyl 1-[(4-chlorophenyl)methyl]-4,6,6-triphenylpyridine-2,3-dicarboxylate
• CAS: 1450999-78-6
• 化学式: C₃₄H₂₈ClNO₄
• 分子量: 550.054
• InChiKey: DWHQWGWBNSFSDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl 2-((4-chlorobenzyl)amino)but-2-enedioate 、 1,1,3-三苯基-2-丙炔醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 dimethyl 1-(4-chlorobenzyl)-4,6,6-triphenyl-1,6-dihydropyridine-2,3-dicarboxylate
  参考文献：
  名称：

  Lewis acid-promoted cascade reaction of primary amine, 2-butynedioate, and propargylic alcohol: a convenient approach to 1,2-dihydropyridines and 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones

  摘要：

  1,2-Dihydropyridine-5,6-dicarboxylates were efficiently constructed through a cascade reaction of primary amine, 2-butynedioate and propargylic alcohol in the presence of Lewis acid under mild conditions. As exceptional, 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones were approached when the primary amine was methylamine. Possible mechanism for the formation of 1,2-dihydropyridine skeleton is proposed. The process involves 1,3,4-pentatrien-1-amine as a key intermediate that formed in situ by trapping allenic carbocations with enamines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.076

文献信息

• Lewis acid-promoted cascade reaction of primary amine, 2-butynedioate, and propargylic alcohol: a convenient approach to 1,2-dihydropyridines and 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones
  作者：Guangwei Yin、Yuanxun Zhu、Ningning Wang、Ping Lu、Yanguang Wang

  DOI：10.1016/j.tet.2013.07.076

  日期：2013.9

  1,2-Dihydropyridine-5,6-dicarboxylates were efficiently constructed through a cascade reaction of primary amine, 2-butynedioate and propargylic alcohol in the presence of Lewis acid under mild conditions. As exceptional, 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones were approached when the primary amine was methylamine. Possible mechanism for the formation of 1,2-dihydropyridine skeleton is proposed. The process involves 1,3,4-pentatrien-1-amine as a key intermediate that formed in situ by trapping allenic carbocations with enamines. (C) 2013 Elsevier Ltd. All rights reserved.