2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methanesulfonate | 1245824-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methanesulfonate
• 英文别名: (2-((methylsulfonyl)oxy)phenyl)boronic acid pinacol ester；[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] methanesulfonate
• CAS: 1245824-39-8
• 化学式: C₁₃H₁₉BO₅S
• 分子量: 298.168
• InChiKey: JTFZUGDRSGVJKO-UHFFFAOYSA-N

物化性质

• 沸点：
  425.3±37.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methanesulfonate 在 盐酸 、 sodium periodate 作用下， 以 四氢呋喃 、 氘代氯仿 、 水 为溶剂， 反应 16.55h， 生成
  参考文献：
  名称：

  提高硼酸催化酰胺合成效率的策略

  摘要：

  新型硼酸已被开发用于催化酰胺合成。使用 DFT 进行路易斯酸度估计，并结合收集的动力学数据，可以发现邻（磺酰氧基）苯硼酸，其与现有的最先进的硼酸相比具有优势。获得了脂肪族、芳香族和杂芳香族羧酸以及伯胺和仲胺的有效偶联。

  DOI：

  10.1002/ejoc.202300720
• 作为产物：
  描述：

  2-羟基苯硼酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methanesulfonate
  参考文献：
  名称：

  Generation of Arynes via Ate Complexes of Arylboronic Esters with an ortho-Leaving Group

  摘要：

  An efficient method of generating aryne has been achieved by treating ortho-(trifluoromethanesulfonyloxy)arylboronic acid pinacol ester with tert-or sec-butyllithium. Monitoring the reaction by B-11 NMR has indicated that a boron-ate complex formed in situ is the eventual precursor that converts into aryne near room temperature. The prior formation of the ate complex at a low temperature has enabled us to use various arynophiles, including those bearing base-sensitive groups. The ready availability of the aryne precursors and mutual orthogonality in aryne generation with widely used ortho-silylaryl triflate have enhanced the utility of the method.

  DOI：

  10.1021/ol401140d

文献信息

• Directed Ortho Borylation of Phenol Derivatives Catalyzed by a Silica-Supported Iridium Complex
  作者：Kenji Yamazaki、Soichiro Kawamorita、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/ol101493m

  日期：2010.9.17

  The directed ortho borylation of phenol derivatives protected with an N,N-diethylcarbamoyl group was efficiently catalyzed by an immobilized monophosphine-Ir system, which was prepared in situ from [Ir(OMe)(cod)](2) and a silica-supported, compact phosphine. The utility of the carbamoyloxy group as a leaving group for metal-catalyzed cross-coupling reactions was demonstrated by its utilization in the synthesis of a terphenyl derivative.