1-(trimethylsilyl)methyl-2-trimethylsilyl-1H-indene

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1-(trimethylsilyl)methyl-2-trimethylsilyl-1H-indene
• 英文别名: trimethyl-[(2-trimethylsilyl-1H-inden-1-yl)methyl]silane
• 化学式: C₁₆H₂₆Si₂
• 分子量: 274.553
• InChiKey: AAGQXTDHTKNSFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (2-溴苯乙炔基)三甲基硅烷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 二异丁基氢化铝 、 二乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 328.5h， 生成 1-(trimethylsilyl)methyl-2-trimethylsilyl-1H-indene
  参考文献：
  名称：

  Diisobutylaluminum Hydride Promoted Cyclization of o-(Trimethylsilylethynyl)styrenes to Indenes

  摘要：

  The reaction of o-(trimethylsilylethynyl)styrenes with diisobutylaluminum hydride (DIBAL-H) provides 2-trimethylsilyl-1H-indenes efficiently. The cyclization mechanism involves regioselective hydroalumination of the alkynyl moiety, geometrical isomerization of the alkenylaluminums formed, and intramolecular carboalumination. With substrates bearing a 2-(trimethylsilyl)ethenyl group (R-1 = Me3Si, R-2 = R-3 = H), bis-silylated benzofulvenes are obtained upon treatment of the reaction mixture with an excess amount of benzaldehyde.

  DOI：

  10.1021/jo501383v

文献信息

• Diisobutylaluminum Hydride Promoted Cyclization of <i>o</i>-(Trimethylsilylethynyl)styrenes to Indenes
  作者：Hidenori Kinoshita、Nobuyoshi Hirai、Katsukiyo Miura

  DOI：10.1021/jo501383v

  日期：2014.9.5

  The reaction of o-(trimethylsilylethynyl)styrenes with diisobutylaluminum hydride (DIBAL-H) provides 2-trimethylsilyl-1H-indenes efficiently. The cyclization mechanism involves regioselective hydroalumination of the alkynyl moiety, geometrical isomerization of the alkenylaluminums formed, and intramolecular carboalumination. With substrates bearing a 2-(trimethylsilyl)ethenyl group (R-1 = Me3Si, R-2 = R-3 = H), bis-silylated benzofulvenes are obtained upon treatment of the reaction mixture with an excess amount of benzaldehyde.