2,3-bis(trimethylsilylethynyl)-1-trideuteriomethoxybenzene | 874758-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3-bis(trimethylsilylethynyl)-1-trideuteriomethoxybenzene
• 英文别名: Trimethyl-[2-[2-(trideuteriomethoxy)-6-(2-trimethylsilylethynyl)phenyl]ethynyl]silane
• CAS: 874758-29-9
• 化学式: C₁₇H₂₄OSi₂
• 分子量: 303.524
• InChiKey: ZYYGECHZQPASAT-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-bis(trimethylsilylethynyl)-1-trideuteriomethoxybenzene 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以86%的产率得到2,3-diethynyl-1-trideuteriomethoxybenzene
  参考文献：
  名称：

  Ortho Effect in the Bergman Cyclization:  Interception of p-Benzyne Intermediate by Intramolecular Hydrogen Abstraction

  摘要：

  Intramolecular hydrogen atom (H-atom) abstraction from the o-OCH3 group effectively intercepts the p-benzyne intermediate in the Bergman cycloaromatization of 2,3-diethynyl-1-methoxybenzene (1) before this intermediate undergoes either retro-Bergman ring opening or external H-atom abstraction. This process leads to the formation of a new diradical and renders the cyclization step essentially irreversible. Chemical and kinetic consequences of this phenomenon were investigated through the combination of computational and experimental studies.

  DOI：

  10.1021/jo051857n
• 作为产物：
  描述：

  2-iodo-1-trideuteriomethoxy-3-nitrobenzene 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 copper(l) iodide 、 二异丙胺 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 37.33h， 生成 2,3-bis(trimethylsilylethynyl)-1-trideuteriomethoxybenzene
  参考文献：
  名称：

  Ortho Effect in the Bergman Cyclization:  Interception of p-Benzyne Intermediate by Intramolecular Hydrogen Abstraction

  摘要：

  Intramolecular hydrogen atom (H-atom) abstraction from the o-OCH3 group effectively intercepts the p-benzyne intermediate in the Bergman cycloaromatization of 2,3-diethynyl-1-methoxybenzene (1) before this intermediate undergoes either retro-Bergman ring opening or external H-atom abstraction. This process leads to the formation of a new diradical and renders the cyclization step essentially irreversible. Chemical and kinetic consequences of this phenomenon were investigated through the combination of computational and experimental studies.

  DOI：

  10.1021/jo051857n

文献信息

• Ortho Effect in the Bergman Cyclization:  Interception of <i>p</i>-Benzyne Intermediate by Intramolecular Hydrogen Abstraction
  作者：Tarek A. Zeidan、Mariappan Manoharan、Igor V. Alabugin

  DOI：10.1021/jo051857n

  日期：2006.2.1

  Intramolecular hydrogen atom (H-atom) abstraction from the o-OCH3 group effectively intercepts the p-benzyne intermediate in the Bergman cycloaromatization of 2,3-diethynyl-1-methoxybenzene (1) before this intermediate undergoes either retro-Bergman ring opening or external H-atom abstraction. This process leads to the formation of a new diradical and renders the cyclization step essentially irreversible. Chemical and kinetic consequences of this phenomenon were investigated through the combination of computational and experimental studies.