Benzo<3,4>cyclodec-3-ene-1,5-diyne-8-ol | 157528-01-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: Benzo<3,4>cyclodec-3-ene-1,5-diyne-8-ol
• 英文别名: 5,6,11,12-Tetradehydro-7,8,9,10-tetrahydrobenzo[10]annulen-8-ol；5,6,11,12-tetradehydro-7,8,9,10-tetrahydrobenzo[10]annulen-8-ol
• CAS: 157528-01-3
• 化学式: C₁₄H₁₂O
• 分子量: 196.249
• InChiKey: UHGNKLTUMZNJCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Benzo<3,4>cyclodec-3-ene-1,5-diyne-8-ol 在 1,4-环己二烯 作用下， 以 氘代苯 为溶剂， 以84%的产率得到1,2,3,4-Tetrahydro-[2]anthrol
  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 、 六甲基磷酰三胺 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 76.5h， 生成 Benzo<3,4>cyclodec-3-ene-1,5-diyne-8-ol
  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