3-(4-methoxyphenyl)-5,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxaborol-2(5H)-ol | 1611477-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxyphenyl)-5,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxaborol-2(5H)-ol
• 英文别名: 2-[2-Hydroxy-3-(4-methoxyphenyl)-5,5-dimethyloxaborol-4-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[2-hydroxy-3-(4-methoxyphenyl)-5,5-dimethyloxaborol-4-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1611477-63-4
• 化学式: C₁₈H₂₆B₂O₅
• 分子量: 344.023
• InChiKey: PSSIPRUPQSGDDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(3-羟基-3-甲基丁-1-炔基)-4-甲氧基苯 、 联硼酸频那醇酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.5h， 以94%的产率得到3-(4-methoxyphenyl)-5,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxaborol-2(5H)-ol
  参考文献：
  名称：

  Trans-Diborylation of Alkynes: Pseudo-Intramolecular Strategy Utilizing a Propargylic Alcohol Unit

  摘要：

  We present the first trans-selective diborylation reaction of alkynes. By means of theoretical calculation-assisted reaction analysis, we designed a pseudo-intramolecular reaction of diboron, propargyl alcohol, and a base to facilitate B-B bond activation and C-B bond formation with high efficiency. This approach provides synthetically versatile and densely functionalized 4-borylated 1,2-oxaborol-2(5H)-oles (vinyldiboronates) in a straightforward manner. Detailed computational analysis showed that the directing alkoxide functionality markedly lowers the activation energy of B-C bond formation.

  DOI：

  10.1021/ja5036754

文献信息

• <i>Trans</i>-Diborylation of Alkynes: <i>Pseudo</i>-Intramolecular Strategy Utilizing a Propargylic Alcohol Unit
  作者：Yuki Nagashima、Keiichi Hirano、Ryo Takita、Masanobu Uchiyama

  DOI：10.1021/ja5036754

  日期：2014.6.18

  We present the first trans-selective diborylation reaction of alkynes. By means of theoretical calculation-assisted reaction analysis, we designed a pseudo-intramolecular reaction of diboron, propargyl alcohol, and a base to facilitate B-B bond activation and C-B bond formation with high efficiency. This approach provides synthetically versatile and densely functionalized 4-borylated 1,2-oxaborol-2(5H)-oles (vinyldiboronates) in a straightforward manner. Detailed computational analysis showed that the directing alkoxide functionality markedly lowers the activation energy of B-C bond formation.