1,2-二溴-3,6-二甲氧基-4,5-二甲基苯 | 19965-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2-二溴-3,6-二甲氧基-4,5-二甲基苯
• 英文名称: 2,3-dibromo-5,6-dimethylhydroquinone dimethyl ether
• 英文别名: 1,2-dibromo-3,6-dimethoxy-4,5-dimethylbenzene；4,5-dibromo-3,6-dimethoxy-1,2-dimethylbenzene；5,6-dibromo-2,3-dimethyl-1,4-dimethoxybenzene；5.6-Dibrom-2.3-dimethyl-hydrochinon-dimethylaether
• CAS: 19965-41-4
• 化学式: C₁₀H₁₂Br₂O₂
• 分子量: 324.012
• InChiKey: OWYDPUOOCVUCTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1,2-二溴-3,6-二甲氧基-4,5-二甲基苯 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 六甲基磷酰三胺 、 copper(l) iodide 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 51.0h， 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 溴 、 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 25.0h， 生成 1,2-二溴-3,6-二甲氧基-4,5-二甲基苯
  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。
• New Benzo[ b ]xanthones from Diels-Alder Reactions of Chromone-3-carboxaldehydes with ortho -Benzoquinodimethanes
  作者：Angela Sandulache、Artur M. S. Silva、Jos� A. S. Cavaleiro

  DOI：10.1007/s00706-002-0567-7

  日期：2003.3.1

  New benzo[b]xanthone derivatives, having substituents in the A and D rings, were prepared from cycloaddition reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethanes, generated in situ from 1,3-dihydrobenzo[c]thiophene 2,2-dioxide, followed by oxidation of the obtained diastereomeric adducts. The structure of all compounds was fully established by 1D and 2D NMR, MS, and elemental analysis. The stereochemistry of the obtained diastereomeric cycloadducts was established by NOESY experiments.
• ——
  作者：Miguel A. Mendez-Rojas、Krzysztof Ejsmont、William H. Watson

  DOI：10.1023/a:1020287802834

  日期：——

  A six-step synthesis was used to prepare a 5,6-dibromobenzoquinone-phenyl maleimide adduct (8). The structure of (8) and four of the intermediates are described. This dibromide is used as the starting material for the synthesis of 2-amino-1,2,3-triazoles which reacts with aldehydes and ketones to prepare materials for nonlinear optical studies. The crystal structures of five compounds were determined. (2) Pbca, a = 8.4183(7), b = 7.2479(7), c = 31.272(3) Angstrom; (3) P-1, a = 8.2023(8), b = 8.8130(8), c = 9.3555(9) Angstrom, alpha = 61.517(1), beta = 73.630(1), gamma = 86.788(2)degrees; (4) P2(1)/c, a = 11.181(1), b = 7.9157(7), c = 15.248(1) Angstrom, beta = 90.691(2)degrees; (7) Pbca, a = 10.300(1), b = 20.184(3), c = 23.469(3) Angstrom; (8) P2(1)/n, a = 6.8975(6), b = 17.877(2), c = 14.089(1) Angstrom, beta = 91.968(2)degrees.
• Furuichi, Kimiaki; Tada, Hitoshi; Kanehira, Aki, Journal of the Chemical Society. Perkin transactions II, 1992, # 12, p. 2169 - 2178
  作者：Furuichi, Kimiaki、Tada, Hitoshi、Kanehira, Aki、Lee, Mie、Kato, Masahiko、et al.

  DOI：——

  日期：——
• 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.