triisopropyl(2-(p-tolylethynyl)phenylthio)silane | 955024-69-8

• 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: triisopropyl(2-(p-tolylethynyl)phenylthio)silane
• 英文别名: [2-[2-(4-Methylphenyl)ethynyl]phenyl]sulfanyl-tri(propan-2-yl)silane；[2-[2-(4-methylphenyl)ethynyl]phenyl]sulfanyl-tri(propan-2-yl)silane
• CAS: 955024-69-8
• 化学式: C₂₄H₃₂SSi
• 分子量: 380.67
• InChiKey: NBUTYUIMVMAYME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  triisopropyl(2-(p-tolylethynyl)phenylthio)silane 在 gold(I) chloride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以96%的产率得到triisopropyl(2-p-tolylbenzo[b]thiophen-3-yl)silane
  参考文献：
  名称：

  Gold-Catalyzed Cyclization of (ortho-Alkynylphenylthio)silanes:  Intramolecular Capture of the Vinyl−Au Intermediate by the Silicon Electrophile

  摘要：

  The gold-catalyzed cyclization of (ortho-alkynylphenylthio)si lanes 1 produced the corresponding 3-silylbenzo[b]thiophenes 2 in good to excellent yields. For example, the reaction of [2-(1-pentynyl)phenylthio]triisopropylsilane 1a, [2-(p-anisylethynyl)phenylthio]triisopropylsilane 1e, and (2-(phenylethynyl)phenylthio]triisopropyl si lane 1g in the presence of 2 mol % of AuCl in toluene at 45 degrees C gave 2a, 2e, and 2g in 98, 99, and 97% yields, respectively. This reaction proceeds through intramolecular capture of the vinyl-Au intermediate by the silicon electrophile, so-called silyldemetalation.

  DOI：

  10.1021/ol701951n
• 作为产物：
  描述：

  4-甲苯基乙炔 在 tris(dibenzylideneacetone)dipalladium (0) 、 palladium dichloride copper(l) iodide 、 三乙胺 、 三苯基膦 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 triisopropyl(2-(p-tolylethynyl)phenylthio)silane
  参考文献：
  名称：

  Gold-Catalyzed Cyclization of (ortho-Alkynylphenylthio)silanes:  Intramolecular Capture of the Vinyl−Au Intermediate by the Silicon Electrophile

  摘要：

  The gold-catalyzed cyclization of (ortho-alkynylphenylthio)si lanes 1 produced the corresponding 3-silylbenzo[b]thiophenes 2 in good to excellent yields. For example, the reaction of [2-(1-pentynyl)phenylthio]triisopropylsilane 1a, [2-(p-anisylethynyl)phenylthio]triisopropylsilane 1e, and (2-(phenylethynyl)phenylthio]triisopropyl si lane 1g in the presence of 2 mol % of AuCl in toluene at 45 degrees C gave 2a, 2e, and 2g in 98, 99, and 97% yields, respectively. This reaction proceeds through intramolecular capture of the vinyl-Au intermediate by the silicon electrophile, so-called silyldemetalation.

  DOI：

  10.1021/ol701951n