1-Bromo-3-<(tert-butyldimethylsilyl)oxy>-6-(2'-ethynylphenyl)hex-5-yne | 157528-04-6

• 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: 1-Bromo-3-<(tert-butyldimethylsilyl)oxy>-6-(2'-ethynylphenyl)hex-5-yne
• 英文别名: [1-Bromo-6-(2-ethynylphenyl)hex-5-yn-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 157528-04-6
• 化学式: C₂₀H₂₇BrOSi
• 分子量: 391.423
• InChiKey: HKNSTUWOSPGNRM-UHFFFAOYSA-N

物化性质

• 沸点：
  424.1±45.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  1-Bromo-3-<(tert-butyldimethylsilyl)oxy>-6-(2'-ethynylphenyl)hex-5-yne 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以94%的产率得到3-<(tert-Butyldimethylsilyl)oxy>-6-(2'-ethynylphenyl)-1-iodohex-5-yne
  参考文献：
  名称：

  Arene 1,4-Diradical Formation from o-Dialkynylarenes

  摘要：

  A series of 10-membered cyclic 1,5-diynes has been prepared with arene rings fused at positions C-3/C-4. The arenes include simple benzene rings, a naphthoquinone and naphthohydroquinone, and an anthraquinone and anthracene unit. Consistent with a simple picture relating the extent of double bond character in the ene part of the ene-diyne with the rate of arene-l,l-diyl formation, the hydroquinone derivatives were much less reactive compared to the corresponding quinones. Substituents such as propargylic hydroxyl or keto group have a small but significant activating effect. The parent 3,4-benzo-1,8-decadiyne shows a half-life for rearrangement of 24 h at 84 degrees C while the corresponding alkene, cyclodec-3-ene-1,5-diyne is reported to have a half-life of 18 h at 37 degrees C.

  DOI：

  10.1021/jo00096a057
• 作为产物：
  描述：

  2-(2-乙炔基苯基)乙炔基三甲基硅烷 在 2,6-二甲基吡啶 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-Bromo-3-<(tert-butyldimethylsilyl)oxy>-6-(2'-ethynylphenyl)hex-5-yne
  参考文献：
  名称：

  Arene 1,4-Diradical Formation from o-Dialkynylarenes

  摘要：

  A series of 10-membered cyclic 1,5-diynes has been prepared with arene rings fused at positions C-3/C-4. The arenes include simple benzene rings, a naphthoquinone and naphthohydroquinone, and an anthraquinone and anthracene unit. Consistent with a simple picture relating the extent of double bond character in the ene part of the ene-diyne with the rate of arene-l,l-diyl formation, the hydroquinone derivatives were much less reactive compared to the corresponding quinones. Substituents such as propargylic hydroxyl or keto group have a small but significant activating effect. The parent 3,4-benzo-1,8-decadiyne shows a half-life for rearrangement of 24 h at 84 degrees C while the corresponding alkene, cyclodec-3-ene-1,5-diyne is reported to have a half-life of 18 h at 37 degrees C.

  DOI：

  10.1021/jo00096a057