8-Bromo-4-methyl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9-tetraene | 1313898-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 8-Bromo-4-methyl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9-tetraene
• 英文别名: 8-bromo-4-methyl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9-tetraene
• CAS: 1313898-56-4
• 化学式: C₁₃H₁₂BrNO
• 分子量: 278.148
• InChiKey: YFHCDNSRVNHWLY-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：
  0.38
• 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-tetraene 、 3-氟-4-甲氧基苯硼酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 作用下， 以 正丁醇 为溶剂， 生成
  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 、 2-硝基苯磺酰肼 、 sodium hydride 、 三乙胺 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 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-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

文献信息

• 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.