12,15-Dimethoxy-13,14-dimethyltricyclo[9.4.0.02,4]pentadeca-1(15),2(4),11,13-tetraen-9-yn-3-one | 911820-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 12,15-Dimethoxy-13,14-dimethyltricyclo[9.4.0.02,4]pentadeca-1(15),2(4),11,13-tetraen-9-yn-3-one
• CAS: 911820-73-0
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: IWZQJUNTAYVHEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12,15-Dimethoxy-13,14-dimethyltricyclo[9.4.0.02,4]pentadeca-1(15),2(4),11,13-tetraen-9-yn-3-one 在 ammonium cerium(IV) nitrate 、 1,4-环己二烯 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 5.75h， 生成 2,3-dimethyl-5,6,7,8-tetrahydroanthracene-1,4-dione
  参考文献：
  名称：

  Two-Photon Photochemical Generation of Reactive Enediyne

  摘要：

  p-Quinoid cyclopropenone-containing enediyne precursor (1) has been synthesized by monocyclopropanation of one of the triple bonds in p-dimethoxy-substituted 3,4-benzocyclodeca-1,5-diyne followed by oxidative demethylation. Cyclopropenone 1 is stable up to 90 C but readily produces reactive enediyne 2 upon single-photon (Phi(300nm) = 0.46) or two-photon (sigma(800nm) = 0.5 GM) photolysis. The photoproduct 2 undergoes Bergman cyclization at 40 degrees C with the lifetime of 88 h.

  DOI：

  10.1021/jo061285m
• 作为产物：
  描述：

  2,3-(octa-1,7-diyne-1,8-diyl)-5,6-dimethyl-1,4-hydroquinone dimethyl ether 、 氯仿 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以86%的产率得到12,15-Dimethoxy-13,14-dimethyltricyclo[9.4.0.02,4]pentadeca-1(15),2(4),11,13-tetraen-9-yn-3-one
  参考文献：
  名称：

  Two-Photon Photochemical Generation of Reactive Enediyne

  摘要：

  p-Quinoid cyclopropenone-containing enediyne precursor (1) has been synthesized by monocyclopropanation of one of the triple bonds in p-dimethoxy-substituted 3,4-benzocyclodeca-1,5-diyne followed by oxidative demethylation. Cyclopropenone 1 is stable up to 90 C but readily produces reactive enediyne 2 upon single-photon (Phi(300nm) = 0.46) or two-photon (sigma(800nm) = 0.5 GM) photolysis. The photoproduct 2 undergoes Bergman cyclization at 40 degrees C with the lifetime of 88 h.

  DOI：

  10.1021/jo061285m

文献信息

• Two-Photon Photochemical Generation of Reactive Enediyne
  作者：Andrei Poloukhtine、Vladimir V. Popik

  DOI：10.1021/jo061285m

  日期：2006.9.1

  p-Quinoid cyclopropenone-containing enediyne precursor (1) has been synthesized by monocyclopropanation of one of the triple bonds in p-dimethoxy-substituted 3,4-benzocyclodeca-1,5-diyne followed by oxidative demethylation. Cyclopropenone 1 is stable up to 90 C but readily produces reactive enediyne 2 upon single-photon (Phi(300nm) = 0.46) or two-photon (sigma(800nm) = 0.5 GM) photolysis. The photoproduct 2 undergoes Bergman cyclization at 40 degrees C with the lifetime of 88 h.