5-chloro-2-[2-(4-methylphenyl)ethynyl]-1H-indole | 1434159-99-5

• 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: 5-chloro-2-[2-(4-methylphenyl)ethynyl]-1H-indole
• CAS: 1434159-99-5
• 化学式: C₁₇H₁₂ClN
• 分子量: 265.742
• InChiKey: HFFLYFPNEBXTDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  5-chloro-2-[2-(4-methylphenyl)ethynyl]-1H-indole 在 copper(l) iodide 、 sodium azide 、 氧气 、 sodium hydride 作用下， 以 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (9-chloroindolo[1,2-a]quinoxalin-6-yl)(p-tolyl)methanone
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Ketoindoloquinoxalines and Indolotriazoloquinoxalines from 1-(2-Nitroaryl)-2-alkynylindoles

  摘要：

  A one-pot protocol for the diversity-oriented synthesis of two indole-based annulated polyheterocycles, ketoindoloquinoxalines and indolotriazoloquinoxalines, has been described. The salient features of the methodology involves either a metal/O2-catalyzed aminooxygenation or a [3 + 2] cycloaddition pathway.

  DOI：

  10.1021/jo402783p

文献信息

• Gold-Catalyzed Sequential Alkyne Activation: One-Pot Synthesis of NH-Carbazoles via Cascade Hydroarylation of Alkyne/6-Endo-Dig Carbocyclization Reactions
  作者：Srinivas Samala、Anil K. Mandadapu、Mohammad Saifuddin、Bijoy Kundu

  DOI：10.1021/jo400799b

  日期：2013.7.5

  efficient one-pot protocol for the synthesis of NH-carbazoles has been described. The strategy comprises a one-pot reaction involving the treatment of 2-alkynyl indoles with arylacetylenes in the presence of an Au–Ag combination catalyst. The salient feature of the strategy involves sequential activation of terminal and internal alkynes leading to the cascade hydroarylation of terminal alkynes and 6-endo-dig

  已经描述了用于合成NH-咔唑的简单且有效的一锅法方案。该策略包括一锅反应，涉及在Au-Ag混合催化剂存在下用芳基乙炔处理2-炔基吲哚。该策略的显着特征涉及末端炔烃和内部炔烃的顺序活化，从而导致末端炔烃的级联加氢芳基化和6-内位-挖碳环化反应。通过使用一系列的2-炔基吲哚和芳基乙炔已经证明了该方法的普遍性。
• Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
  作者：Rajesh K Arigela、Sudhir K Sharma、Brijesh Kumar、Bijoy Kundu

  DOI：10.3762/bjoc.9.41

  日期：——

  A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.

  一种微波辅助的三组分方案涉及2-炔基吲哚的N-1烷基化与环氧氯丙烷的环开反应，以及内部炔烃-1,3-双极环加成的分子内Huisgen叠氮化合物的串联序列。该方法的有效性已通过处理各种2-炔基吲哚（芳香族/脂肪族）与环氧氯丙烷和叠氮化钠，产生了合格的环丁二嗪三唑并环四环吲哚衍生物的收率来证明。
• Diversity-Oriented Synthesis of Ketoindoloquinoxalines and Indolotriazoloquinoxalines from 1-(2-Nitroaryl)-2-alkynylindoles
  作者：Srinivas Samala、Rajesh K Arigela、Ruchir Kant、Bijoy Kundu

  DOI：10.1021/jo402783p

  日期：2014.3.21

  A one-pot protocol for the diversity-oriented synthesis of two indole-based annulated polyheterocycles, ketoindoloquinoxalines and indolotriazoloquinoxalines, has been described. The salient features of the methodology involves either a metal/O2-catalyzed aminooxygenation or a [3 + 2] cycloaddition pathway.