1-(methoxymethyl)indole-2-carboxylic acid | 40899-78-3

• 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: 1-(methoxymethyl)indole-2-carboxylic acid
• 英文别名: 1-Methoxymethylindol-2-carbonsaeure；N-(methoxymethyl)indole-2-carboxylic acid
• CAS: 40899-78-3
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: UJXJMJOTBKACNC-UHFFFAOYSA-N

物化性质

• 沸点：
  401.7±25.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(methoxymethyl)indole-2-carboxylic acid 在 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Multicomponent Synthesis and Biological Evaluation of a Piperazine-Based Dopamine Receptor Ligand Library

  摘要：

  A series of 1,4-disubstituted piperazine-based compounds were designed, synthesized, and evaluated as dopamine D2/D3 receptor ligands. The synthesis relies on the key multicomponent split-Ugi reaction, assessing its great potential in generating chemical diversity around the piperazine core. With the aim of evaluating the effect of such diversity on the dopamine receptor affinity, a small library of compounds was prepared, applying post-Ugi transformations. Ligand stimulated binding assays indicated that some compounds show a significant affinity, with K-i values up to 53 nM for the D2 receptor. Molecular docking studies with the D2 and D3 receptor homology models were also performed on selected compounds. They highlighted key interactions at the indole head and at the piperazine moiety, which resulted in good agreement with the known pharmacophore models, thus helping to explain the observed structure-activity relationship data. Molecular insights from this study could enable a rational improvement of the split-Ugi primary scaffold, toward more selective ligands.

  DOI：

  10.1021/acsmedchemlett.5b00131
• 作为产物：
  描述：

  Ethyl 1-(methoxymethyl)indole-2-carboxylate 在 乙醇 、 sodium hydroxide 作用下， 生成 1-(methoxymethyl)indole-2-carboxylic acid
  参考文献：
  名称：

  [4 + 2]环化或丢失重排：铑催化发散合成具有抗癌活性的咔啉衍生物

  摘要：

  已经实现了一种不寻常的铑催化的 C–H 活化/Lossen 重排/oxa-Michael 加成串联环化以及众所周知的可调 C–H 活化/[4 + 2] 环化，从而导致区域-、化学-和非对映选择性获得多种五环α-咔啉和β-咔啉-1-酮衍生物，产率中等至良好，具有显着的抗癌活性。

  DOI：

  10.1021/acs.orglett.4c01050

文献信息

• Palladium-catalysed decarboxylative nitrile insertion via C–H activation or self-coupling of indole-2-carboxylic acids: a new route to indolocarbolines and triindoles
  作者：R. N. Prasad Tulichala、K. C. Kumara Swamy

  DOI：10.1039/c5cc03160e

  日期：——

  Palladium catalysed-reaction of indole carboxylic acids with nitriles in the presence of Ag2CO3 proceeds via decarboxylative dual C-H activation leading to the nitrile insertion products, triazaindeno-fluorenes (indolocarbolines); in the absence...

  在Ag2CO3存在下，吲哚羧酸与腈的钯催化反应通过脱羧双CH活化进行，从而产生腈插入产物三氮杂茚基芴（吲哚并咔啉）；离席期间...
• Fluorescent Diarylindoles by Palladium-Catalyzed Direct and Decarboxylative Arylations of Carboxyindoles
  作者：Mitsuru Miyasaka、Azusa Fukushima、Tetsuya Satoh、Koji Hirano、Masahiro Miura

  DOI：10.1002/chem.200900098

  日期：2009.4.6

  efficiently undergo successive diarylation accompanied by CH bond cleavage and decarboxylation upon treatment with aryl bromides in the presence of a palladium catalyst system to afford fluorescent 2,3‐diarylindoles. This facile synthetic method provides a highly efficient blue emitter with a quantum yield of 0.97 in the solid state (see scheme).

  简单和灿烂：1-取代的1 ħ -吲哚-2-羧酸的有效经历连续diarylation伴随被C 在钯催化剂体系的存在下，得到荧光2,3- diarylindoles与芳基溴化物处理时H键裂解和脱羧。这种简便的合成方法提供了一种高效的蓝色发射器，固态时的量子产率为0.97（请参见方案）。