ethyl 2,3,4,5-tetrahydro-2-hydroxy-5-oxo-4-(2-nitrophenyl)-2-(trifluoromethyl)-1H-indeno[1,2-b]pyridine-3-carboxylate | 1354199-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: ethyl 2,3,4,5-tetrahydro-2-hydroxy-5-oxo-4-(2-nitrophenyl)-2-(trifluoromethyl)-1H-indeno[1,2-b]pyridine-3-carboxylate
• CAS: 1354199-72-6
• 化学式: C₂₂H₁₇F₃N₂O₆
• 分子量: 462.382
• InChiKey: RKFWLOUQPJQZDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  118.77
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  1,3-茚满二酮 、 三氟乙酰乙酸乙酯 、 邻硝基苯甲醛 在 ammonium acetate 、 碘 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以53%的产率得到ethyl 1,3-dihydro-6'-hydroxy-1,3-dioxo-2',4'-di(2-nitrophenyl)-6'-(trifluoromethyl)spiro[indene-2,3'-piperidine]-5'-carboxylate
  参考文献：
  名称：

  Iodine catalyzed one-pot multi-component reaction to CF3-containing spiro[indene-2,3′-piperidine] derivatives

  摘要：

  In the presence of a catalytic amount of molecular iodine (0.1 equiv.), the one-pot multi-component reaction of ethyl trifluoroacetoacetate 1, indan-1,3-dione 2, ammonium acetate 3 and aromatic aldehyde 4 mainly gave the ethyl-6'-hydroxy-1,3-dioxo-2',4'-diary1-6'-(trifluoromethyl)-1,3-dihydrospiro[indene-2,3'-piperidinej-5'-carboxylate derivatives 5, along with the minor product 2-trifluoromethy12,3,4,5-tetrahydro-1H-indeno[1,2-b]pyridine derivatives 6. A plausible reaction mechanism for the formation of 5,6 was presented. The structures of compounds 5,6 were fully confirmed by H-1 NMR, F-19 NMR, MS, IR spectroscopies and elemental analysis or high resolution mass spectra (HRMS). Meanwhile, the representative 5a and 6h were further confirmed by XRD analysis. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.09.006