dimethyl 4'-phenyl-1'-(p-tolyl)-1'H-spiro[fluorene-9,2'-pyridine]-5',6'-dicarboxylate | 1450999-54-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: dimethyl 4'-phenyl-1'-(p-tolyl)-1'H-spiro[fluorene-9,2'-pyridine]-5',6'-dicarboxylate
• 英文别名: Dimethyl 1'-(4-methylphenyl)-4'-phenylspiro[fluorene-9,6'-pyridine]-2',3'-dicarboxylate
• CAS: 1450999-54-8
• 化学式: C₃₄H₂₇NO₄
• 分子量: 513.593
• InChiKey: GEUSFNITWWHEQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• 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：

  9-phenylethynylfluoren-9-ol 、 dimethyl 2-(p-tolylamino)but-2-enedioate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以62%的产率得到dimethyl 4'-phenyl-1'-(p-tolyl)-1'H-spiro[fluorene-9,2'-pyridine]-5',6'-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