4,6,7-tribromo-1H-indole | 1202382-67-9

• 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: 4,6,7-tribromo-1H-indole
• 英文别名: 4,6,7-tribromoindole
• CAS: 1202382-67-9
• 化学式: C₈H₄Br₃N
• 分子量: 353.838
• InChiKey: ARHOXTOEYBQMTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4,6,7-tribromo-1H-indole 在 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 2-硝基苯磺酰肼 、 sodium tert-pentoxide 、 sodium hydride 、 三乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 生成 8-(5,6-Dihydrobenzo[b][1]benzazepin-11-yl)-4-methyl-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9-tetraene
  参考文献：
  名称：

  Application of 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Suzuki–Miyaura and Buchwald–Hartwig Cross-Coupling Reactions for the Preparation of Annulated Indole Libraries

  摘要：

  The construction of an unprecedented class of an indole-based library, namely, a 6,7-annulated-4-substituted 93-member indole library, using a strategic combination of 6,7-indolyne cycloaddition and cross-coupling reactions under both Suzuki-Miyaura and Buchwald-Hartwig conditions is described. This work represents the first example of library development that employs the indole aryne methodology. Annulated indoles, with the exception of only a few biologically active natural products (i.e., the trikentrins, herbindoles, teleocidins, and nodulisporic acids), have no representation in the PubChem or MLSMR databases. These structural entities are therefore predicted to have unique chemical property space characteristics and a high probability of exhibiting interesting biological activity.

  DOI：

  10.1021/co2000289
• 作为产物：
  描述：

  2,4-二溴-6-硝基苯胺 在 亚硝酸特丁酯 、 copper(ll) bromide 作用下， 以 四氢呋喃 为溶剂， 生成 4,6,7-tribromo-1H-indole
  参考文献：
  名称：

  Application of 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Suzuki–Miyaura and Buchwald–Hartwig Cross-Coupling Reactions for the Preparation of Annulated Indole Libraries

  摘要：

  The construction of an unprecedented class of an indole-based library, namely, a 6,7-annulated-4-substituted 93-member indole library, using a strategic combination of 6,7-indolyne cycloaddition and cross-coupling reactions under both Suzuki-Miyaura and Buchwald-Hartwig conditions is described. This work represents the first example of library development that employs the indole aryne methodology. Annulated indoles, with the exception of only a few biologically active natural products (i.e., the trikentrins, herbindoles, teleocidins, and nodulisporic acids), have no representation in the PubChem or MLSMR databases. These structural entities are therefore predicted to have unique chemical property space characteristics and a high probability of exhibiting interesting biological activity.

  DOI：

  10.1021/co2000289

文献信息

• New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development
  作者：Neil Brown、Diheng Luo、Joseph A. Decapo、Keith R. Buszek

  DOI：10.1016/j.tetlet.2009.09.083

  日期：2009.12

  We describe herein an efficient new route to the trikentrins and their related structures using a tandem 6,7-indolyne cycloaddition/Negishi cross-coupling reaction starting from a 4,6,7-tribromoindole (obtained in good yield via the Bartoli indole synthesis). The key step of this second generation route to the trikentrins is based on our observation that the 7-bromo substituent appears to undergo selective

  我们在此描述了使用串联 6,7-吲哚炔环加成/Negishi 交叉偶联反应从 4,6,7-三溴吲哚（通过 Bartoli 吲哚合成以良好产率获得）的三叉链脲及其相关结构的有效新途径. 这条通往trikentrins 的第二代路线的关键步骤是基于我们的观察，即 7-溴取代基似乎经历了选择性金属 - 卤素交换和消除，得到 6,7-吲哚炔，它在过量环戊二烯存在下被捕获. 随后 Negishi 在 4-溴吲哚位置与 Et 2交叉偶联Zn 直接给出了从我们之前的工作中获得的相同中间体。还将描述使用这种通用环加成/交叉偶联策略将这种化学方法应用于构建 trikentrin 相关文库。
• Further Investigations into the Regioselectivity of 6,7-Indole Aryne Cyclo­additions with 2-Substituted Furans: Remarkable Contrasteric Preference Depends­ on Pyrrole and Benzene Ring Substitution
  作者：Keith Buszek、Alok Nerurkar、Nalin Chandrasoma、Lincoln Maina、Allen Brassfield、Diheng Luo、Neil Brown

  DOI：10.1055/s-0033-1338911

  日期：——

  compounds were prepared to study the effects of pyrrole and benzene ring substitution patterns on the regioselectivity of 6,7-indole aryne cycloadditions with 2-tert-butylfuran. The arynes were generated by our metal–halogen exchange/elimination protocol. The results of this investigation reveal that substitution at the 3-position on the indole ring in particular results in remarkable regiocontrol

  本文热忱致力于斯科特教授丹麦在他60之际个生日。 抽象 制备了一系列相关的6,7-二溴吲哚化合物，以研究吡咯和苯环取代方式对2-叔丁基6,7-吲哚亚芳基环加成反应的区域选择性的影响丁基呋喃。芳烃是通过我们的金属-卤素交换/消除方案生成的。这项研究的结果表明，在吲哚环的3位取代特别是导致显着的区域控制，从而有利于对比产品。在该位点的芳香结合显着增强了该作用。然而，大多数4-或5-取代基的存在通常导致选择性显着降低。后一个系列的例外包括4-乙基和4-碘的情况，即使在没有有益的C-3取代基的情况下，这两种情况也主要提供对比产品。 制备了一系列相关的6,7-二溴吲哚化合物，以研究吡咯和苯环取代方式对2-叔丁基6,7-吲哚亚芳基环加成反应的区域选择性的影响丁基呋喃。芳烃是通过我们的金属-卤素交换/消除方案生成的。这项研究的结果表明，在吲哚环的3位取代特别是导致显着的区域控制，从而有利于对比产品。在该
• Application of 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Suzuki–Miyaura and Buchwald–Hartwig Cross-Coupling Reactions for the Preparation of Annulated Indole Libraries
  作者：Paul D. Thornton、Neil Brown、David Hill、Ben Neuenswander、Gerald H. Lushington、Conrad Santini、Keith R. Buszek

  DOI：10.1021/co2000289

  日期：2011.9.12

  The construction of an unprecedented class of an indole-based library, namely, a 6,7-annulated-4-substituted 93-member indole library, using a strategic combination of 6,7-indolyne cycloaddition and cross-coupling reactions under both Suzuki-Miyaura and Buchwald-Hartwig conditions is described. This work represents the first example of library development that employs the indole aryne methodology. Annulated indoles, with the exception of only a few biologically active natural products (i.e., the trikentrins, herbindoles, teleocidins, and nodulisporic acids), have no representation in the PubChem or MLSMR databases. These structural entities are therefore predicted to have unique chemical property space characteristics and a high probability of exhibiting interesting biological activity.