5-甲基-2-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶 | 1101205-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-甲基-2-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶
• 中文别名: 5-甲基吡啶-2-硼酸频哪醇酯
• 英文名称: 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS: 1101205-22-4
• 化学式: C₁₂H₁₈BNO₂
• 分子量: 219.091
• InChiKey: QURLLHHERKWUHA-UHFFFAOYSA-N

物化性质

• 沸点：
  317.8±30.0 °C(Predicted)
• 密度：
  1.02

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

MSDS英文版

反应信息

• 作为反应物：
  描述：

  5-甲基-2-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶 、 2-氯-1,3-二甲苯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 caesium carbonate 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以45%的产率得到2-(2,6-dimethylphenyl)-4-methylpyridine
  参考文献：
  名称：

  Expanding the scope of the Cu assisted Suzuki–Miyaura reaction

  摘要：

  Recent advances in the development of the copper facilitated Suzuki-Miyaura reaction are described. Improvements include expansion of substrate scope to include aryl chlorides and polyhalo aryl boronates. It was found that use of S-Phos and X-Phos could accomplish the coupling of 2-pyridyl boronates to aryl chlorides and bromides in shorter reaction times and in higher yield than previously described with DPPF. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.088
• 作为产物：
  描述：

  3-甲基吡啶 、 频那醇硼烷 在 C₂₈H₄₉OSiY 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以41%的产率得到5-甲基-2-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶
  参考文献：
  名称：

  吡啶与频哪醇硼烷的钇催化邻位选择性 C-H 硼化

  摘要：

  使用频哪醇硼烷对多种吡啶进行邻位选择性 C-H 硼化反应是通过钇催化实现的。值得注意的是，通过使用适当的配体/金属组合有效地抑制了可能的硼氢化副反应。得到的 2-吡啶基硼酸盐经过进一步的转化，例如 Suzuki-Miyaura 偶联或 Chan-Lam 胺化。

  DOI：

  10.1002/anie.202117750

文献信息

• P2X3, RECEPTOR ANTAGONISTS FOR TREATMENT OF PAIN
  申请人：Burgey Christopher S.

  公开号：US20110206783A1

  公开（公告）日：2011-08-25

  The subject invention relates to novel P2X 3 receptor antagonists that play a critical role in treating disease states associated with pain, in particular peripheral pain, inflammatory pain, or tissue injury pain that can be treated using a P2X 3 receptor subunit modulator.

  本发明涉及一种新型P2X3受体拮抗剂，该拮抗剂在治疗与疼痛有关的疾病状态中发挥关键作用，特别是可以使用P2X3受体亚单位调节剂治疗的外周疼痛、炎症性疼痛或组织损伤疼痛。
• P2X3, receptor antagonists for treatment of pain
  申请人：Burgey Christopher S.

  公开号：US08598209B2

  公开（公告）日：2013-12-03

  The subject invention relates to novel P2X3 receptor antagonists that play a critical role in treating disease states associated with pain, in particular peripheral pain, inflammatory pain, or tissue injury pain that can be treated using a P2X3 receptor subunit modulator.

  本发明涉及新型P2X3受体拮抗剂，对于治疗与疼痛有关的疾病状态，特别是可以使用P2X3受体亚单位调节剂治疗的外周疼痛，炎症性疼痛或组织损伤疼痛起着关键作用。
• Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates
  作者：James Z. Deng、Daniel V. Paone、Anthony T. Ginnetti、Hideki Kurihara、Spencer D. Dreher、Steven A. Weissman、Shaun R. Stauffer、Christopher S. Burgey

  DOI：10.1021/ol802556f

  日期：2009.1.15

  The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(l) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope Is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.
• Expanding the scope of the Cu assisted Suzuki–Miyaura reaction
  作者：Brendan M. Crowley、Craig M. Potteiger、James Z. Deng、Christopher K. Prier、Daniel V. Paone、Christopher S. Burgey

  DOI：10.1016/j.tetlet.2011.07.088

  日期：2011.9

  Recent advances in the development of the copper facilitated Suzuki-Miyaura reaction are described. Improvements include expansion of substrate scope to include aryl chlorides and polyhalo aryl boronates. It was found that use of S-Phos and X-Phos could accomplish the coupling of 2-pyridyl boronates to aryl chlorides and bromides in shorter reaction times and in higher yield than previously described with DPPF. (C) 2011 Elsevier Ltd. All rights reserved.
• Yttrium‐Catalyzed <i>ortho</i> ‐Selective C−H Borylation of Pyridines with Pinacolborane
  作者：Yuncong Luo、Shengjie Jiang、Xin Xu

  DOI：10.1002/anie.202117750

  日期：2022.5.16

  The ortho-selective C−H borylation of a wide range of pyridines using pinacolborane was achieved through yttrium catalysis. Notably, the possible hydroboration side reaction was effectively suppressed by using the proper ligand/metal combination. The resultant 2-pyridyl boronates were subjected to further transformations such as a Suzuki–Miyaura coupling or the Chan–Lam amination.

  使用频哪醇硼烷对多种吡啶进行邻位选择性 C-H 硼化反应是通过钇催化实现的。值得注意的是，通过使用适当的配体/金属组合有效地抑制了可能的硼氢化副反应。得到的 2-吡啶基硼酸盐经过进一步的转化，例如 Suzuki-Miyaura 偶联或 Chan-Lam 胺化。