7-氯-4-吲哚羧酸甲酯 | 503816-69-1

• 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
• 中文名称: 7-氯-4-吲哚羧酸甲酯
• 英文名称: 7-chloro-1H-indole-4-carboxylic acid methyl ester
• 英文别名: 4-carbomethoxy-7-chloroindole；Methyl 7-chloro-1H-indole-4-carboxylate
• CAS: 503816-69-1
• 化学式: C₁₀H₈ClNO₂
• 分子量: 209.632
• InChiKey: YMAVXLSGYDNOML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-氯-4-吲哚羧酸甲酯 、 苯硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) cesium bicarbonate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以80%的产率得到
  参考文献：
  名称：

  Practical Synthesis and Elaboration of Methyl 7-Chloroindole-4-carboxylate

  摘要：

  A synthesis of a previously unknown indole derivative is presented. The route reported herein allows for the preparation of multihundred gram quantities of material without any chromatographic purification. Conditions are presented for the Pd-catalyzed elaboration of one of the "diversity generating elements" of this important pharmacophore.

  DOI：

  10.1021/jo026434p
• 作为产物：
  描述：

  Methyl 3-amino-4-chloro-2-[2-(2,2-dimethylpropanoyloxy)-1-methylsulfanylethyl]benzoate 在 吡啶 、 硫酸 、 双氧水 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 7-氯-4-吲哚羧酸甲酯
  参考文献：
  名称：

  Practical Synthesis and Elaboration of Methyl 7-Chloroindole-4-carboxylate

  摘要：

  A synthesis of a previously unknown indole derivative is presented. The route reported herein allows for the preparation of multihundred gram quantities of material without any chromatographic purification. Conditions are presented for the Pd-catalyzed elaboration of one of the "diversity generating elements" of this important pharmacophore.

  DOI：

  10.1021/jo026434p

文献信息

• Synthesis of diverse indole libraries on polystyrene resin – Scope and limitations of an organometallic reaction on solid supports
  作者：Kerstin Knepper、Sylvia Vanderheiden、Stefan Bräse

  DOI：10.3762/bjoc.8.132

  日期：——

  The synthesis of diverse substituted indole structures on solid supports is described. The immobilization of nitrobenzoic acid onto Merrifield resin and the subsequent treatment with alkenyl Grignard reagents delivered indole carboxylates bound to solid supports. In contrast to results in the liquid phase, ortho,ortho-unsubstituted nitroarenes also delivered indole moieties in good yields. Subsequent

  描述了在固体支持物上合成多种取代的吲哚结构。将硝基苯甲酸固定在 Merrifield 树脂上并随后用链烯基格氏试剂处理将吲哚羧酸盐结合到固体载体上。与液相中的结果相反，邻位、邻位未取代的硝基芳烃也以良好的产率递送吲哚部分。随后的钯催化反应（Suzuki、Heck、Sonogashira、Stille）在裂解后通过四个步骤以中等至良好的产率传递所需的分子。介绍了范围和限制。
• [EN] DIMERIC IAP INHIBITORS<br/>[FR] INHIBITEURS IAP DIMÉRIQUES
  申请人：NOVARTIS AG

  公开号：WO2012080271A1

  公开（公告）日：2012-06-21

  The present invention provides compounds of formula M-L-M' (where M and M' are each independently a monomeric moiety of Formula (I) and L is a linker). The dimeric compounds have been found to be effective in promoting apoptosis in rapidly dividing cells. (I)

  本发明提供了公式M-L-M'的化合物（其中M和M'分别独立地是公式（I）的单体基团，L是连接基团）。已发现二聚化合物在促进快速分裂细胞凋亡方面具有有效性。（I）
• Bartoli Indole Synthesis on Solid Supports
  作者：Kerstin Knepper、Stefan Bräse

  DOI：10.1021/ol034851y

  日期：2003.8.1

  [reaction: see text] Bartoli indole synthesis has been performed for the first time on solid supports. Starting from Merrifield resin, immobilization of five nitro benzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic cleavage leads to substituted methyl indole carboxylates in excellent purities. Features of this reaction are the stability of halide groups, ester

  [反应：见正文]首次在固体载体上进行Bartoli吲哚合成。从Merrifield树脂开始，进行了五种硝基苯甲酸的固定化。添加四种不同的烯基格利雅试剂和进行碱性裂解，可得到纯度极高的取代的甲基吲哚羧酸盐。该反应的特征是卤化物基团的稳定性，酯部分和o，o′-未取代的硝基树脂的耐受性。固定的吲哚也可能发生Heck和Sonogashira反应。
• DIMERIC IAP INHIBITORS
  申请人：Chen Zhuoliang

  公开号：US20130309247A1

  公开（公告）日：2013-11-21

  The present invention provides compounds of formula M-L-M′ (where M and M′ are each independently a monomeric moiety of Formula (I) and L is a linker). The dimeric compounds have been found to be effective in promoting apoptosis in rapidly dividing cells. (I)

  本发明提供了公式M-L-M'的化合物（其中M和M'分别独立地是公式（I）的单体基团，L是连接剂）。已发现二聚化合物在促进快速分裂细胞的凋亡方面具有有效性。 (I)
• 4,7-Disubstituted indoles and methods of making
  申请人：IRM LLC

  公开号：US20040110944A1

  公开（公告）日：2004-06-10

  The present invention provides, compounds, methods and compositions of biologically important indoles. In addition, the present invention provides synthesis methods for substituting leaving groups at positions 4 and 7 of the indole ring as diversity generating elements.