2-(2'-(dimesitylboryl)phenylethynyl)pyridine | 1268447-88-6

• 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
• 英文名称: 2-(2'-(dimesitylboryl)phenylethynyl)pyridine
• 英文别名: 2-(2'-BMes2-phenylethynyl)pyridine；[2-(2-Pyridin-2-ylethynyl)phenyl]-bis(2,4,6-trimethylphenyl)borane；[2-(2-pyridin-2-ylethynyl)phenyl]-bis(2,4,6-trimethylphenyl)borane
• CAS: 1268447-88-6
• 化学式: C₃₁H₃₀BN
• 分子量: 427.397
• InChiKey: MQGLHIQBQPBZNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  574.4±50.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2'-(dimesitylboryl)phenylethynyl)pyridine 以 四氢呋喃 、 甲苯 为溶剂， 反应 168.5h， 生成
  参考文献：
  名称：

  The opposite and amplifying effect of B ← N coordination on photophysical properties of regioisomers with an unsymmetrical backbone

  摘要：

  具有相反归纳效应并且可以形成内部B ← N键的“二分”的取代基，如PhBMes2和py，已被发现对具有非对称骨架的区域异构体的电子和光物理性质具有明显影响。

  DOI：

  10.1039/c8sc04210a
• 作为产物：
  描述：

  2-溴吡啶 、 (2-ethynylphenyl)dimesitylborane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到2-(2'-(dimesitylboryl)phenylethynyl)pyridine
  参考文献：
  名称：

  Donor−Acceptor Assisted Alkyne Hydration: A Luminescent Boron-Stabilized Enol

  摘要：

  An alkyne molecule 2-(2'-BMes(2)-phenylethynyl)pyridine (1) that contains a Lewis acidic BMes(2) group and a Lewis basic pyridyl group has been found to undergo facile hydration under ambient conditions in the presence of Cul, forming a highly emissive and stable enol ester (2). The lack of any hydration reactivity by a control compound 2-(2'-BMes(2)-phenylethynyl)benzene (3) under the same conditions supports that the cooperativity between the Lewis donor and acceptor groups plays a key role in the formation of 2.

  DOI：

  10.1021/ol200106a

文献信息

• Double Cyclization/Aryl Migration Across an Alkyne Bond Enabled by Organoboryl and Diarylplatinum Groups
  作者：Christina Sun、Zachary M. Hudson、Leanne D. Chen、Suning Wang

  DOI：10.1002/anie.201201781

  日期：2012.6.4

  metals: Diarylacetylenes 1, containing both a boryl (BMes2) group and a diarylplatinum group, undergo a transformation involving a double metallocyclization/aryl migration to give tetracycles 2 in high diastereoselectivity (see scheme). This remarkable transformation is enabled by the synergistic interplay of the boryl and the diarylplatinum group.

  金属之间的协同作用：Diarylacetylenes 1，同时含有硼（BMES 2）基团和一个diarylplatinum基，经历涉及双metallocyclization /芳基的迁移，得到tetracycles变换2在高非对映选择性（参见方案）。硼基和二芳基铂基团的协同相互作用使得这种显着的转化成为可能。
• The opposite and amplifying effect of B ← N coordination on photophysical properties of regioisomers with an unsymmetrical backbone
  作者：Chao Zeng、Kang Yuan、Nan Wang、Tai Peng、Gang Wu、Suning Wang

  DOI：10.1039/c8sc04210a

  日期：——

  “Dichotomic” substituents such as PhBMes₂ and py that have opposite inductive effects and can form an internal B ← N bond have been found to have a distinct impact on the electronic and photophysical properties of regioisomers with an unsymmetrical backbone.

  具有相反归纳效应并且可以形成内部B ← N键的“二分”的取代基，如PhBMes2和py，已被发现对具有非对称骨架的区域异构体的电子和光物理性质具有明显影响。
• Donor−Acceptor Assisted Alkyne Hydration: A Luminescent Boron-Stabilized Enol
  作者：Christina Sun、Jiasheng Lu、Suning Wang

  DOI：10.1021/ol200106a

  日期：2011.3.4

  An alkyne molecule 2-(2'-BMes(2)-phenylethynyl)pyridine (1) that contains a Lewis acidic BMes(2) group and a Lewis basic pyridyl group has been found to undergo facile hydration under ambient conditions in the presence of Cul, forming a highly emissive and stable enol ester (2). The lack of any hydration reactivity by a control compound 2-(2'-BMes(2)-phenylethynyl)benzene (3) under the same conditions supports that the cooperativity between the Lewis donor and acceptor groups plays a key role in the formation of 2.