7-methyl-2-(p-tolyl)-1H-indole | 906782-97-6

• 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: 7-methyl-2-(p-tolyl)-1H-indole
• 英文别名: 7-methyl-2-(4-methylphenyl)-1H-indole
• CAS: 906782-97-6
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: YCMVLXQSVSNDCM-UHFFFAOYSA-N

物化性质

• 沸点：
  407.2±14.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 7-methyl-2-(p-tolyl)-1H-indole 、 N-(2-methoxyethyl)-N-(pyrrolidin-3-yl)methanesulfonamide 在 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以17.8%的产率得到N-(2-methoxyethyl)-N-(1-((7-methyl-2-(p-tolyl)-1H-indol-3-yl)methyl)pyrrolidin-3-yl)methanesulfonamide
  参考文献：
  名称：

  2-Phenylindole and Arylsulphonamide: Novel Scaffolds Bactericidal against Mycobacterium tuberculosis

  摘要：

  A cellular activity-based screen on Mycobacterium tuberculosis (Mtb) H37Rv using a focused library from the AstraZeneca corporate collection led to the identification of 2-phenylindoles and arylsulphonamides, novel antimycobacterial scaffolds. Both the series were bactericidal in vitro and in an intracellular macrophage infection model, active against drug sensitive and drug resistant Mtb clinical isolates, and specific to mycobacteria. The scaffolds showed promising structure-activity relationships; compounds with submicromolar cellular potency were identified during the hit to lead exploration. Furthermore, compounds from both scaffolds were tested for inhibition of known target enzymes or pathways of antimycobacterial drugs including InhA, RNA polymerase, DprE1, topoisomerases, protein synthesis, and oxidative-phosphorylation. Compounds did not inhibit any of the targets suggesting the potential of a possible novel mode of action(s). Hence, both scaffolds provide the opportunity to be developed further as leads and tool compounds to uncover novel mechanisms for tuberculosis drug discovery.

  DOI：

  10.1021/ml5001933
• 作为产物：
  描述：

  在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium tert-butylate 、 双(2-二苯基磷苯基)醚 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以56%的产率得到7-methyl-2-(p-tolyl)-1H-indole
  参考文献：
  名称：

  镍催化亚胺向不同的吲哚分子内直接芳基化

  摘要：

  已经开发出具有挑战性的芳基氯化物的亚胺的有效的镍催化的分子内直接芳基化。多功能的镍催化利用容易获得的亚胺，并提供了对生物和药物化学相当重要的装饰多样化的2-芳基吲哚。

  DOI：

  10.1021/acs.orglett.9b00600

文献信息

• Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters
  作者：Jiechun Liu、Haojiang Lin、Huanfeng Jiang、Liangbin Huang

  DOI：10.1021/acs.orglett.1c03679

  日期：2022.1.21

  Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis

  多取代吲哚普遍存在于药物、农用化学品和有机材料中。本文提出的事实是，多官能化吲哚可以由容易获得的肟酯和芳基碘化物有效构建，包括钯/降冰片烯协同合成。该反应是由钯/降冰片烯协同催化中的一类独特的亲电子试剂实现的，它们是从简单的酮衍生的肟酯。广泛的底物范围和高官能团耐受性使该方法对合成多取代吲哚具有吸引力。
• Palladium-Catalyzed Cascade Process Consisting of Isocyanide Insertion and Benzylic C(sp³)–H Activation: Concise Synthesis of Indole Derivatives
  作者：Takeshi Nanjo、Chihiro Tsukano、Yoshiji Takemoto

  DOI：10.1021/ol302035j

  日期：2012.8.17

  Synthesis of the indole skeleton was achieved using a Pd-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)–H activation. It was found that slow addition of isocyanide is effective for reducing the amount of catalyst needed and Ad2PnBu is a good ligand for C(sp3)–H activation. The construction of the tetracyclic carbazole skeleton was also achieved by a Pd-catalyzed domino

  吲哚骨架的合成是通过Pd催化的级联过程完成的，该过程由异氰酸酯插入和苄基C（sp 3）–H活化组成。研究发现，缓慢添加异氰酸酯可有效减少所需催化剂的量，而Ad 2 P n Bu是C（sp 3）–H活化的良好配体。四环咔唑骨架的构建也通过掺有炔烃插入的Pd催化的多米诺反应来实现。
• Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines
  作者：G. Eliad Benitez-Medina、Sofía Ortiz-Soto、Armando Cabrera、Manuel Amézquita-Valencia

  DOI：10.1002/ejoc.201900394

  日期：2019.6.23

  A palladium‐catalyzed tandem reaction for synthesis of 2‐arylindoles is described. The process involves a condensation/reduction/condensation/heteroannulation to give the respective indole. Furthermore, it also features satisfactory yields and selectivities.

  描述了钯催化的串联反应，用于合成2-芳基吲哚。该方法涉及缩合/还原/缩合/异环化，得到各自的吲哚。此外，它还具有令人满意的产率和选择性。