ethyl 4,4-di(1H-indol-3-yl)butanoate | 1165946-62-2

• 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 4,4-di(1H-indol-3-yl)butanoate
• CAS: 1165946-62-2
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: QYDQVLQRBCRZMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.88
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl 4,4-di(1H-indol-3-yl)butanoate 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4,4-di(1H-indol-3-yl)butanoic acid
  参考文献：
  名称：

  Exploring bis-(indolyl)methane moiety as an alternative and innovative CAP group in the design of histone deacetylase (HDAC) inhibitors

  摘要：

  In order to gather further knowledge about the structural requirements on histone deacetylase inhibitors (HDACi), starting from the schematic model of the common pharmacophore that characterizes this class of molecules (surface recognition CAP group-connection unit-linker region-Zinc Binding Group), we designed and synthesized a series of hydroxamic acids containing a bis-(indolyl) methane moiety. HDAC inhibition pro. le and antiproliferative activity were evaluated. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.101
• 作为产物：
  描述：

  吲哚 、 4-氧代丁酸乙基酯 在 dysprosium(III) trifluoromethanesulfonate 作用下， 以 甲醇 、 水 为溶剂， 生成 ethyl 4,4-di(1H-indol-3-yl)butanoate
  参考文献：
  名称：

  Exploring bis-(indolyl)methane moiety as an alternative and innovative CAP group in the design of histone deacetylase (HDAC) inhibitors

  摘要：

  In order to gather further knowledge about the structural requirements on histone deacetylase inhibitors (HDACi), starting from the schematic model of the common pharmacophore that characterizes this class of molecules (surface recognition CAP group-connection unit-linker region-Zinc Binding Group), we designed and synthesized a series of hydroxamic acids containing a bis-(indolyl) methane moiety. HDAC inhibition pro. le and antiproliferative activity were evaluated. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.101

文献信息

• Double π-Bond Isomerization/Friedel-Crafts Reaction Involving γ-­Amidocronates: Access to γ-Aryl/Heteroaryl GABA Scaffolds and Dihydropyrido[1,2-<i>a</i>]indoles
  作者：Anvita Srivastava、Sampak Samanta

  DOI：10.1002/ejoc.201501388

  日期：2016.2

  resultant N-protected enamines at room temperature by using B(C6F5)3 (5 mol-%) as an efficient Lewis acid catalyst. Moreover, the easy synthesis of the important class of 8,9-dihydropyrido[1,2-a]indole scaffolds was realized by this unique procedure. Thus, a simple, convenient, and metal-free-based protocol may provide an alternative powerful synthetic route for heteroarylation/arylation at the γ positions

  通过在 N-保护的 γ-氨基巴豆酸酯/γ-氨基巴豆酮的 π-键异构化，获得了一系列具有药理学吸引力的 γ-吲哚基/呋喃基/芳基取代的 γ-氨基酯/γ-氨基酮。三乙胺，然后使用 B(C6F5)3 (5 mol-%) 作为有效的路易斯酸催化剂，在室温下进行涉及几种吲哚/呋喃/芳烃衍生物的串联 Friedel-Crafts 烷基化反应和所得的 N 保护的烯胺。此外，通过这种独特的程序实现了重要类别 8,9-二氢吡啶并 [1,2-a] 吲哚支架的轻松合成。因此，一种简单、方便且不含金属的方案可以以实用的方式为 GABA 衍生物的 γ 位置的杂芳基化/芳基化提供另一种强大的合成路线。
• Ga(III) Catalyzed Addition of Indole Derivatives and Different Propiolates
  作者：Xun Zhu、Xiuqin Zhou、Dongsheng Xiang

  DOI：10.3987/com-15-13248

  日期：——

  Ga(III) was used to catalyze Michael addition of indole derivatives to different propiolates in aqueous solution. Good to excellent yields were obtained under our reaction conditions.