trimethyl(1,4,7-trimethyl-1,4-dihydro-1,4-epoxynaphthalen-5-yl)silane | 1437769-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: trimethyl(1,4,7-trimethyl-1,4-dihydro-1,4-epoxynaphthalen-5-yl)silane
• 英文别名: Trimethyl-(1,5,8-trimethyl-11-oxatricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraen-3-yl)silane
• CAS: 1437769-80-6
• 化学式: C₁₆H₂₂OSi
• 分子量: 258.436
• InChiKey: BLADSKJFSPCIAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,5-二甲基呋喃 、 4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trimethylsilyl)phenyl trifluoromethanesulfonate 在 仲丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 0.5h， 以81%的产率得到trimethyl(1,4,7-trimethyl-1,4-dihydro-1,4-epoxynaphthalen-5-yl)silane
  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