8-Bromo-4-methyl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaene | 1202382-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-Bromo-4-methyl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaene
• 英文别名: 8-bromo-4-methyl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaene
• CAS: 1202382-70-4
• 化学式: C₁₃H₁₀BrNO
• 分子量: 276.132
• InChiKey: QMDHDWWFHPAYBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-Bromo-4-methyl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaene 在 2-硝基苯磺酰肼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到8-Bromo-4-methyl-14-oxa-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 正丁基锂 、 亚硝酸特丁酯 、 sodium hydride 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 8-Bromo-4-methyl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaene
  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。
• 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.