1,4-Dihydro-1,4-dioxonaphtho<3,4-b>cyclodec-3-ene-1,5-diyne | 142672-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-Dihydro-1,4-dioxonaphtho<3,4-b>cyclodec-3-ene-1,5-diyne
• 英文别名: Tricyclo[8.8.0.03,8]octadeca-1(10),3,5,7-tetraen-11,17-diyne-2,9-dione；tricyclo[8.8.0.03,8]octadeca-1(10),3,5,7-tetraen-11,17-diyne-2,9-dione
• CAS: 142672-70-6
• 化学式: C₁₈H₁₂O₂
• 分子量: 260.292
• InChiKey: NDORVNHFVDNGER-UHFFFAOYSA-N

物化性质

• 沸点：
  406.4±45.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-Dihydro-1,4-dioxonaphtho<3,4-b>cyclodec-3-ene-1,5-diyne 在 1,4-环己二烯 作用下， 以 氘代苯 为溶剂， 以79%的产率得到1,2,3,4-tetrahydronaphthacene-6,11-quinone
  参考文献：
  名称：

  Arene 1,4-diradical formation from o-dialkynylarenes

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)92066-5
• 作为产物：
  描述：

  2,3-二溴-1,4-萘醌 在 copper(l) iodide 、 四(三苯基膦)钯 哌啶 、 potassium fluoride 、 正丁基锂 、 sodium dithionite 、 ammonium cerium(IV) nitrate 、 sodium hydride 作用下， 反应 15.0h， 生成 1,4-Dihydro-1,4-dioxonaphtho<3,4-b>cyclodec-3-ene-1,5-diyne
  参考文献：
  名称：

  Arene 1,4-diradical formation from o-dialkynylarenes

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)92066-5

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.