2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)quinoline
• 英文别名: 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinaldine；8-borylquinaldine；2-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
• 化学式: C₁₆H₂₀BNO₂
• 分子量: 269.151
• InChiKey: MKPHVSBPACLBOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)quinoline 在 正丁基锂 、 sodium perborate tetrahydrate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 4.08h， 生成 (2-methylquinolin-8-yl)methanol
  参考文献：
  名称：

  现场选择C ？二氧化硅支撑的磷铱体系催化的C8位喹啉的氢硼化

  摘要：

  位点选择性Ç  H在C8位置喹啉衍生物的硼基化已经通过使用基于二氧化硅负载笼型monophosphane配体SMAP非均相铱催化剂系统来实现。促肾上腺皮质激素释放因子的有效合成1（CRF 1）受体基于后期阶段C拮抗剂 ħ硼化策略演示C8硼化反应的效用。

  DOI：

  10.1002/asia.201301423
• 作为产物：
  描述：

  8-羟基喹哪啶 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)quinoline
  参考文献：
  名称：

  Palladium-Catalyzed Borylation of Aryl Halides or Triflates with Dialkoxyborane:  A Novel and Facile Synthetic Route to Arylboronates

  摘要：

  A direct borylation of aryl halides or triflates with dialkoxyborane was investigated. The coupling reaction of pinacolborane with aryl halides or triflates in the presence of a catalytic amount of PdCl2(dppf) together with a base provided arylboronates in high yields. The product distributions were strongly dependent on the base employed, and the tertiary amine, especially Et3N, was effective for the selective formation of the boron-carbon bond. The reaction conditions were so mild that arylboronates having a variety of functional groups such as carbonyl, cyano, and nitro groups were readily prepared.

  DOI：

  10.1021/jo991337q

文献信息

• Palladium-Catalyzed Borylation of Aryl Halides or Triflates with Dialkoxyborane:  A Novel and Facile Synthetic Route to Arylboronates
  作者：Miki Murata、Takashi Oyama、Shinji Watanabe、Yuzuru Masuda

  DOI：10.1021/jo991337q

  日期：2000.1.1

  A direct borylation of aryl halides or triflates with dialkoxyborane was investigated. The coupling reaction of pinacolborane with aryl halides or triflates in the presence of a catalytic amount of PdCl2(dppf) together with a base provided arylboronates in high yields. The product distributions were strongly dependent on the base employed, and the tertiary amine, especially Et3N, was effective for the selective formation of the boron-carbon bond. The reaction conditions were so mild that arylboronates having a variety of functional groups such as carbonyl, cyano, and nitro groups were readily prepared.
• Site-Selective CH Borylation of Quinolines at the C8 Position Catalyzed by a Silica-Supported Phosphane-Iridium System
  作者：Shota Konishi、Soichiro Kawamorita、Tomohiro Iwai、Patrick G. Steel、Todd B. Marder、Masaya Sawamura

  DOI：10.1002/asia.201301423

  日期：2014.2

  Site‐selective CH borylation of quinoline derivatives at the C8 position has been achieved by using a heterogeneous Ir catalyst system based on a silica‐supported cage‐type monophosphane ligand SMAP. The efficient synthesis of a corticotropin‐releasing factor1 (CRF1) receptor antagonist based on a late‐stage CH borylation strategy demonstrates the utility of the C8 borylation reaction.

  位点选择性Ç  H在C8位置喹啉衍生物的硼基化已经通过使用基于二氧化硅负载笼型monophosphane配体SMAP非均相铱催化剂系统来实现。促肾上腺皮质激素释放因子的有效合成1（CRF 1）受体基于后期阶段C拮抗剂 ħ硼化策略演示C8硼化反应的效用。