1,4-dimethoxy-2,3-dimethyl-5,6-bis(trimethylsilanylethynyl)benzene | 700847-01-4

• 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: 1,4-dimethoxy-2,3-dimethyl-5,6-bis(trimethylsilanylethynyl)benzene
• 英文别名: 1,2-bis(trimethylsilylethynyl)-3,6-dimethoxy-4,5-dimethylbenzene；2-[2,5-Dimethoxy-3,4-dimethyl-6-(2-trimethylsilylethynyl)phenyl]ethynyl-trimethylsilane；2-[2,5-dimethoxy-3,4-dimethyl-6-(2-trimethylsilylethynyl)phenyl]ethynyl-trimethylsilane
• CAS: 700847-01-4
• 化学式: C₂₀H₃₀O₂Si₂
• 分子量: 358.628
• InChiKey: CWCDAPYCHJRUIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dimethoxy-2,3-dimethyl-5,6-bis(trimethylsilanylethynyl)benzene 在 六甲基磷酰三胺 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 27.0h， 生成 2,3-(octa-1,7-diyne-1,8-diyl)-5,6-dimethyl-1,4-hydroquinone dimethyl ether
  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：

  2,3-二甲基氢醌 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 copper(l) iodide 、 溴 、 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 49.0h， 生成 1,4-dimethoxy-2,3-dimethyl-5,6-bis(trimethylsilanylethynyl)benzene
  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

• Synthesis and properties of p-benzoquinone-fused hexadehydro[18]annulenes
  作者：Tohru Nishinaga、Yasuo Miyata、Nobutake Nodera、Koichi Komatsu

  DOI：10.1016/j.tet.2004.02.041

  日期：2004.4

  A series of hexadehydro[18]annulenes fused with different numbers of p-benzoquinone, 4-6, were synthesized by stepwise transformation of the p-dimethoxybenzene moiety of the precursor dehydroannulene 3 fused with three 3,6-dimethoxy-4,5-dimethylbenzene units at 1,2-positions into p-benzoquinone using ceric ammonium nitrate. The UV–vis spectra of compounds 4 and 5, which have both electron-donating

  一系列hexadehydro的[18]轮烯稠合具有不同数目的p醌，4 - 6，通过分步转化合成p前驱dehydroannulene的-dimethoxybenzene部分3具有三个-3,6-二甲氧基-4,5-稠合用硝酸铈铵将1,2-位的二甲基苯单元合成对苯醌。紫外可见化合物的光谱4和5，其具有两个供电子p -dimethoxybenzene单元（S）和电子接受p在该π系统苯醌单元（S），结果显示最大的吸收带相比红移与3仅具有p -dimethoxybenzene单元和6仅具有p醌单元。但是，发现对4和5的溶剂化变色作用很弱，可能是因为HOMO和LUMO（B3LYP / 6-31G（d））不在整个π系统上而是局部化的。
• 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.