(2-(benzo[b]thiophen-2-yl)-5-methyl-1,3,2-dioxaborinan-5-yl)methanol | 1209496-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (2-(benzo[b]thiophen-2-yl)-5-methyl-1,3,2-dioxaborinan-5-yl)methanol
• CAS: 1209496-06-9
• 化学式: C₁₃H₁₅BO₃S
• 分子量: 262.137
• InChiKey: OCVKAEZUKJSTGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  447.5±15.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2-(benzo[b]thiophen-2-yl)-5-methyl-1,3,2-dioxaborinan-5-yl)methanol 在 sodium hydride 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling Reaction of Heteroaryltriolborates with Aryl Halides for Synthesis of Biaryls

  摘要：

  Cyclic triolborates possessing a heteroaromatic ring on the boron atom [ArB(OCH2)(3)CHCH3]M (M=K, Na, Li) were prepared in high yields from heteroarylboronic acids, 1,1,1-tris(hydroxymethyl)ethane (triol) and KOH or NaH. The corresponding lithium salts were synthesized from aryllithiums, B(OMe)(3) and triol. They were air-stable white solids that were convenient for handling in air. High performance of these triolborates for metal-catalyzed bond-forming reactions was demonstrated in palladium-catalyzed cross-coupling reactions with haloarenes. Although the use of heteroarylboronic acids often results in very low yields due to competitive hydrolytic B-C bond cleavage with water under typical conditions using aqueous bases, triolborates possessing a 2-pyridyl, 3-pyridyl or 2-thiophenyl ring afforded biaryls in high yields at 50-120 degrees C in anhydrous DMF. There was a strong accelerating effect of CuI for reactions of 2- and 3-pyridylborate derivatives, whereas 2-thiophenyl derivatives reacted smoothly resulting in high yields in the absence of CuI.

  DOI：

  10.3987/com-09-s(s)30
• 作为产物：
  描述：

  1,1,1-三(羟甲基)乙烷 、 苯并噻吩-2-硼酸 以 甲苯 为溶剂， 生成 (2-(benzo[b]thiophen-2-yl)-5-methyl-1,3,2-dioxaborinan-5-yl)methanol
  参考文献：
  名称：

  No-carrier-added radioiodination of triolborates, water-soluble complexes of boronic acids

  摘要：

  已开发出一种便捷快速的合成方法，能够从水溶性复合物中制备标记有碘-123的芳基和杂芳基碘化物，这些复合物源自芳基和杂芳基硼酸。版权所有 © 2010 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1831

文献信息

• Silyl-protected dioxaborinanes: application in the Suzuki cross-coupling reaction
  作者：Sean Goggins、Eleanor Rosevere、Clément Bellini、Joseph C. Allen、Barrie J. Marsh、Mary F. Mahon、Christopher G. Frost

  DOI：10.1039/c3ob42099j

  日期：——

  The synthesis of a range of novel silyl-protected dioxaborinanes as a column- and bench-stable boron reagent were found to be advantageous to achieving good yields in palladium-catalysed cross-coupling reactions under standard conditions.

  一系列新型硅烷保护的双氧硼烷的合成，作为柱和实验台稳定的硼试剂，被发现有利于在标准条件下实现钯催化交叉偶联反应的高产率。
• Triolborates: water-soluble complexes of arylboronic acids as precursors to iodoarenes
  作者：Murthy R. Akula、Min-Liang Yao、George W. Kabalka

  DOI：10.1016/j.tetlet.2009.12.074

  日期：2010.2

  A facile synthesis of aryl and heteroaryl iodides from water-soluble complexes of aryl- and heteroarylboronic acids has been developed. (C) 2010 Elsevier Ltd. All rights reserved.