3-bromo-2-cyclopropyl-2,1-borazaronaphthalene | 1616634-95-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-bromo-2-cyclopropyl-2,1-borazaronaphthalene
• 英文别名: 3-Bromo-2-cyclopropyl-1,2-dihydrobenzo[e][1,2]azaborinine；3-bromo-2-cyclopropyl-1H-1,2-benzazaborinine
• CAS: 1616634-95-7
• 化学式: C₁₁H₁₁BBrN
• 分子量: 247.93
• InChiKey: DGTFSHLIIQGLPD-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85 °C
• 沸点：
  311.0±52.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-2-cyclopropyl-2,1-borazaronaphthalene 、 N-Boc-4-碘哌啶 在 4-乙基吡啶 、 锰 、 氟硼酸钠 、 4,4'-二甲基-2,2'-联吡啶 、 氯化镍二甲氧基乙烷 作用下， 以 N,N-二甲基乙酰胺 、 环己烷 为溶剂， 反应 18.0h， 以88%的产率得到3-(4-(N-Boc)piperidenyl)-2-cyclopropyl-2,1-borazaronaphthalene
  参考文献：
  名称：

  Reductive Cross-Coupling of 3-Bromo-2,1-borazaronaphthalenes with Alkyl Iodides

  摘要：

  Conditions have been developed for the reductive cross-coupling of 3-bromo-2,1-borazaronaphthalenes with primary and secondary alkyl iodides. This method allows direct alkylation of azaborine cores, providing efficient access to functionalized isosteres of naphthalene derivatives.

  DOI：

  10.1021/ol501495d
• 作为产物：
  描述：

  2-cyclopropyl-2,1-borazaronaphthalene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到3-bromo-2-cyclopropyl-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates

  摘要：

  Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.

  DOI：

  10.1021/jo5011894

文献信息

• Suzuki–Miyaura Cross-Coupling of Brominated 2,1-Borazaronaphthalenes with Potassium Alkenyltrifluoroborates
  作者：Gary A. Molander、Steven R. Wisniewski、Elham Etemadi-Davan

  DOI：10.1021/jo502260x

  日期：2014.11.21

  Conditions have been developed for the palladium-catalyzed cross-coupling of 3-bromo-2,1-borazaronaphthalenes with potassium alkenyltrifluoroborates. Twenty-seven alkenyl-substituted azaborines have been synthesized through this method, providing access to a family of 2,1-borazaronaphthalenes with alkenyl substitution at the C3 position.
• Reductive Cross-Coupling of 3-Bromo-2,1-borazaronaphthalenes with Alkyl Iodides
  作者：Gary A. Molander、Steven R. Wisniewski、Kaitlin M. Traister

  DOI：10.1021/ol501495d

  日期：2014.7.18

  Conditions have been developed for the reductive cross-coupling of 3-bromo-2,1-borazaronaphthalenes with primary and secondary alkyl iodides. This method allows direct alkylation of azaborine cores, providing efficient access to functionalized isosteres of naphthalene derivatives.
• Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates
  作者：Gary A. Molander、Steven R. Wisniewski

  DOI：10.1021/jo5011894

  日期：2014.7.18

  Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.