ethyl 3-dimethylaminomethyl-2-indolylacetate | 252637-04-0

• 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 3-dimethylaminomethyl-2-indolylacetate
• 英文别名: ethyl 3-[(dimethylamino)methyl]-1H-indole-2-acetate；ethyl 2-[3-[(dimethylamino)methyl]-1H-indol-2-yl]acetate
• CAS: 252637-04-0
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: ZPFZRAMJWCMJOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-dimethylaminomethyl-2-indolylacetate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis of new biologically active isothiazolo[4,5-b]carbazole-type tetracyclic derivatives via an indole-2,3-quinodimethane approach

  摘要：

  A number of isothiazolo[4,5-b]carbazole derivatives were prepared via a Diels Alder approach involving thermally induced indole-2,3-quinodimethane intermediates. Preliminary biological tests revealed a CSK-3 beta kinase inhibitor (29) and some free NH group containing compounds (17d, 19c, 29) displayed selective human carbonic anhydrase I inhibitory activities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.015
• 作为产物：
  描述：

  聚合甲醛 、 吲哚-2-乙酸乙酯 、 二甲胺 以95%的产率得到ethyl 3-dimethylaminomethyl-2-indolylacetate
  参考文献：
  名称：

  Synthesis and resolution of a C2-symmetrical indolo-2,3-quinodimethane dimer

  摘要：

  Thermolysis of ethyl 3-dimethylaminomethyl-2-indolylacetate generated an indolo-2,3-quinodimethane as evidenced by its dimerization to a first '4+2' dimer, which rearranged at a higher temperature to a cyclooctadienic diester. Resolution of this last diester in the form of the amides derived from (-)-alpha-methyl-benzylamine proved it to be C-2-symmetrical. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01348-9

文献信息

• The gramine route to the Diels-Alder adducts of indolo-2,3-quinodimethanes
  作者：Khalid Diker、Michèle Döéde Maindreville、Daniel Royer、Fabien Le Provost、Jean Lévy

  DOI：10.1016/s0040-4039(99)01349-0

  日期：1999.10

  Indolo-2,3-quinodimethanes were smoothly generated by thermal fragmentation of 2-substituted 3-aminomethylindoles, and engaged in Diers-Alder reactions yielding 1,2,3,4-tetrahydrocarbazoles with a large array of possible substituents at either position. An intramolecular variant of the procedure generated a tetracyclic (unnatural) indolomonoterpene with complete control of three stereocenters. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis and resolution of a C2-symmetrical indolo-2,3-quinodimethane dimer
  作者：Khalid Diker、Michèle Döé de Maindreville、Jean Lévy

  DOI：10.1016/s0040-4039(99)01348-9

  日期：1999.10

  Thermolysis of ethyl 3-dimethylaminomethyl-2-indolylacetate generated an indolo-2,3-quinodimethane as evidenced by its dimerization to a first '4+2' dimer, which rearranged at a higher temperature to a cyclooctadienic diester. Resolution of this last diester in the form of the amides derived from (-)-alpha-methyl-benzylamine proved it to be C-2-symmetrical. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of new biologically active isothiazolo[4,5-b]carbazole-type tetracyclic derivatives via an indole-2,3-quinodimethane approach
  作者：Raimundo F. Miambo、Marie Laronze-Cochard、Ata-Martin Lawson、Régis Guillot、Brigitte Baldeyrou、Amélie Lansiaux、Claudiu T. Supuran、Janos Sapi

  DOI：10.1016/j.tet.2014.09.015

  日期：2014.11

  A number of isothiazolo[4,5-b]carbazole derivatives were prepared via a Diels Alder approach involving thermally induced indole-2,3-quinodimethane intermediates. Preliminary biological tests revealed a CSK-3 beta kinase inhibitor (29) and some free NH group containing compounds (17d, 19c, 29) displayed selective human carbonic anhydrase I inhibitory activities. (C) 2014 Elsevier Ltd. All rights reserved.