ethyl 2'-amino-6'-(hydroxymethyl)-5-methyl-2,8'-dioxo-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-3'-carboxylate | 1431403-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 2'-amino-6'-(hydroxymethyl)-5-methyl-2,8'-dioxo-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-3'-carboxylate
• 英文别名: ethyl 2'-amino-6'-(hydroxymethyl)-5-methyl-2,8'-dioxospiro[1H-indole-3,4'-pyrano[3,2-b]pyran]-3'-carboxylate
• CAS: 1431403-17-6
• 化学式: C₂₀H₁₈N₂O₇
• 分子量: 398.372
• InChiKey: IHXFUZLNTISHLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  曲酸 、 5-甲基靛红 、 氰乙酸乙酯 在 三乙烯二胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以89%的产率得到ethyl 2'-amino-6'-(hydroxymethyl)-5-methyl-2,8'-dioxo-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-3'-carboxylate
  参考文献：
  名称：

  Three-Component Synthesis of Spiro[Indoline-3,4'-Pyrano[3,2-b]Pyran]- 2,8'-Diones Using a One-Pot Reaction

  摘要：

  本文描述了一种一锅法的三组分反应，其中使用了异靛酮和曲酸与活性亚甲基化合物（如氰基乙酸乙酯、氰基乙酸甲酯和马隆腈）在甲醇中反应，使用催化量的DABCO，在回流条件下有效地生成2'-氨基-6'-(羟甲基)-8'H-螺旋[吲哚-3,4'-吡喃[3,2-b]吡喃]-2,8'-二酮，产率良好到优异。

  DOI：

  10.2174/13862073113166660067

文献信息

• Cu(OTf)2 catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines
  作者：K. Parthasarathy、C. Praveen、C. Balachandran、P. Senthil kumar、S. Ignacimuthu、P.T. Perumal

  DOI：10.1016/j.bmcl.2013.02.086

  日期：2013.5

  Cu(OTf)(2) catalyzed efficient synthesis of spiropyrano[3,2-b]pyran-4(8H)-ones is accomplished via one-pot three component reaction between isatin, kojic acid and active methylenes. This synthetic protocol is operationally simple and affords product with good to excellent yields at a short reaction time. The synthesized compounds were evaluated for their tumor cell growth inhibitory activity against the human lung cancer cell line (A549) and found that 13 compounds exhibited moderate to good anticancer potency. Molecular docking studies were performed for all the synthesized compounds and the results showed that compound 4e showed greater affinity for anaplastic lymphoma kinase (ALK) receptor. (C) 2013 Elsevier Ltd. All rights reserved.
• Three-Component Synthesis of Spiro[Indoline-3,4'-Pyrano[3,2-b]Pyran]- 2,8'-Diones Using a One-Pot Reaction
  作者：Abbas Rahmati、Zahra Khalesi、Tahmineh Kenarkoohi

  DOI：10.2174/13862073113166660067

  日期：2014.1.31

  A one-pot, three-component reaction of an isatin and kojic acid with an active methylene compound such as ethyl cyanoacetate, methyl cyanoacetate and malononitrile in methanol using catalytic amount of DABCO to give 2'- amino-6'-(hydroxymethyl)-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-2,8'-diones in good to excellent yields under reflux conditions, is described.

  本文描述了一种一锅法的三组分反应，其中使用了异靛酮和曲酸与活性亚甲基化合物（如氰基乙酸乙酯、氰基乙酸甲酯和马隆腈）在甲醇中反应，使用催化量的DABCO，在回流条件下有效地生成2'-氨基-6'-(羟甲基)-8'H-螺旋[吲哚-3,4'-吡喃[3,2-b]吡喃]-2,8'-二酮，产率良好到优异。