5,8-diacetoxy-1,4-naphthoquinone | 14569-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-diacetoxy-1,4-naphthoquinone
• 英文别名: Naphthazarin diacetate；(4-acetyloxy-5,8-dioxonaphthalen-1-yl) acetate
• CAS: 14569-45-0
• 化学式: C₁₄H₁₀O₆
• 分子量: 274.23
• InChiKey: DEYKOBAZKKDRES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,8-diacetoxy-1,4-naphthoquinone 在 base 作用下， 生成 (4-乙酰氧基-9,10-二氧代蒽-1-基)乙酸酯
  参考文献：
  名称：

  Echavarren, Antonio; Prados, Pilar; Sol, Gregorio Del, Journal of Chemical Research, Miniprint, 1981, # 10, p. 3675 - 3691

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4,5,8-tetramethoxynaphthalene 在 4-二甲氨基吡啶 、 ammonium cerium (IV) nitrate 、 三乙胺 、 锌 作用下， 以 水 、 乙腈 为溶剂， 生成 5,8-diacetoxy-1,4-naphthoquinone
  参考文献：
  名称：

  10.3184/174751911x556710

  摘要：

  DOI：

  10.3184/174751911x556710

文献信息

• Photoacylation of Electron-Rich Quinones: An Application of the ”Photo-Friedel-Crafts Reaction”
  作者：Jochen Mattay、Christian Schiel、Michael Oelgemöller

  DOI：10.1055/s-2001-15072

  日期：——

  Irradiation of substituted 1,4-benzo- or 1,4-naphthoquinones in the presence of several aldehydes resulted in the formation of acylated hydroquinones in good yields. In the case of 5-acetyloxy naphthoquinone 8, both regioisomers were formed, but the 2,8-isomer was favored in all cases examined. Even acylated tetrahydroxy naphthalenes became available in good yields by this method.

  在多种醛的存在下，对取代的1,4-苯醌或1,4-萘醌进行辐照，得到了良好产率的酰基化氢醌。在5-乙酰氧基萘醌8的情况下，形成了两种区域异构体，但在所有检查的案例中，2,8-异构体都是优先形成的。通过这种方法，甚至获得了良好产率的酰基化四羟基萘。
• Some derivatives of naphthazarin and 2-methylnaphthazarin
  作者：L. A. Cort、P. A. B. Rodriguez

  DOI：10.1039/j39670000949

  日期：——

  preparations of naphthazarin, and 2-methylnaphthazarin have been found to give by-products, which have been identified. 5,8-Dihydroxy-1,3-dimethylnaphtho[2,3-c]furan-4,9-quinone has been synthesised, and its chemistry is described; 2-bromomethylnaphthazarin diacetate has also been obtained. Nuclear magnetic resonance measurements are reported for the naphthoquinones, their precursors, and derivatives.

  已经发现已知的萘达沙林和2-甲基萘达沙林的制剂会产生副产物，这些副产物已被鉴定。合成了5,8-二羟基-1,3-二甲基萘[2,3- c ]呋喃-4,9-醌，并描述了其化学性质；还已经获得了2-溴甲基萘他沙林二乙酸酯。报告了萘醌，它们的前体和衍生物的核磁共振测量结果。
• Synthesis of 2-(3-indolyl)-1,4-naphthoquinones using 3-iodoindoles
  作者：Yasuhiro Tanoue、Moritsugu Hamada、Norihisa Kai、Kazunori Sakata、Mamoru Hashimoto、Takeshi Nagai

  DOI：10.1002/jhet.5570420625

  日期：2005.9

  The usefulness of 3-iodoindoles available for introduction of an indole unit is presented. The reaction of various halo-3-iodoindoles with 1,4-naphthoquinone gave the corresponding 2-(3-indolyl)-1-4,naphthoquinones in moderate yields. The 3-iodoindole was used for synthesis of a compound containing both naph-thazarin and indole skeletons.

  提出了可用于引入吲哚单元的3-碘吲哚的有用性。各种卤代-3-碘吲哚与1，4-萘醌的反应以中等收率得到了相应的2-（3-吲哚基）-1-4，萘醌。3-碘吲哚用于合成同时含有萘他扎林和吲哚骨架的化合物。
• The synthesis and Diels–Alder reactions of 2-prop-2-enylidene-1,3-dioxolan
  作者：Steven V. Ley、William L. Mitchell、Tarur V. Radhakrishnan、Derek H. R. Barton

  DOI：10.1039/p19810001582

  日期：——

  The synthesis and regiospecific Diels–Alder reactions of 2-prop-2-enylidene-1,3-dioxolan (1) are described. Reactions with 1,4-naphthoquinones (5) gave tetrahydroanthraquinones (6). The adduct of (1) with juglone (5d) could be further hydrolysed to 1,8-dihydroxy-9,10-anthraquinone (7).

  描述了2-丙-2-烯叉-1,3-二氧戊环（1）的合成和区域特异性Diels-Alder反应。与1，4-萘醌（5）反应得到四氢蒽醌（6）。（1）与juglone（5d）的加合物可以进一步水解为1,8-二羟基-9,10-蒽醌（7）。
• Synthesis and Structure of a Longitudinally Twisted Hexacene
  作者：Robert G. Clevenger、Bharat Kumar、Elizabeth M. Menuey、Kathleen V. Kilway

  DOI：10.1002/chem.201705676

  日期：2018.3.2

  The addition of phenyllithium to a polycyclic quinone, 9,11,12,21,22,24‐hexaphenyltetrabenzo[a,c,n,p]hexacene‐10,23‐dione (10), followed by SnCl2‐mediated reduction of the diol intermediate, yielded 9,10,11,12,21,22,23,24‐octaphenyltetrabenzo‐[a,c,n,p]hexacene (4). Crystallographic analysis of hexacene 4 showed it to possess a longitudinal twist of 184°, which was in good agreement with AM1 calculations

  在多环醌9,11,12,21,22,24-六苯基四苯并[ a，c，n，p ]己烯10,23-二酮（10）中添加苯基锂，然后用SnCl 2介导还原二醇中间体，生成9,10,11,12,21,22,23,24-八苯基四苯并[ a，c，n，p ]己二烯（4）。己烯4的晶体学分析表明，它具有184°的纵向扭曲，这与AM1的计算非常吻合。化合物4除了是到目前为止合成的最扭曲的并苯 在其子结构中包含最扭曲的萘，蒽，并四苯和并五苯部分。