1,2,3,4-Tetrahydro-7,12-pentacenequinone | 142672-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 1,2,3,4-Tetrahydro-7,12-pentacenequinone
• 英文别名: 8,9,10,11-Tetrahydropentacene-5,14-dione；8,9,10,11-tetrahydropentacene-5,14-dione
• CAS: 142672-74-0
• 化学式: C₂₂H₁₆O₂
• 分子量: 312.368
• InChiKey: RLLACKDQWBVCJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二溴蒽醌 在 copper(l) iodide 、 四(三苯基膦)钯 哌啶 、 potassium fluoride 、 正丁基锂 、 sodium dithionite 、 1,4-环己二烯 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 氘代苯 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 127.0h， 生成 1,2,3,4-Tetrahydro-7,12-pentacenequinone
  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

文献信息

• Arene 1,4-diradical formation from o-dialkynylarenes
  作者：M.F. Semmelhack、Thomas Neu、Francisco Foubelo

  DOI：10.1016/s0040-4039(00)92066-5

  日期：1992.6

  A series of five arene and quinone derivatives with dialkynyl substituents in the ortho positions and fixed in a 10-membered ring were prepared and tested with respect to thermal rearrangement to the corresponding arene 1,4 diradicals.
• Arene 1,4-Diradical Formation from o-Dialkynylarenes
  作者：M. F. Semmelhack、Thomas Neu、Francisco Foubelo

  DOI：10.1021/jo00096a057

  日期：1994.8

  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.