10-nitrosoanthracen-9-ol | 14090-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-nitrosoanthracen-9-ol
• 英文别名: 9,10-anthraquinone-9-oxime；9,10-anthracenedione monooxime；9,10-anthraquinone monooxime；Anthraquinone Monoxime；anthraquinone oxime；anthraquinone monooxime；Anthrachinon-monooxim
• CAS: 14090-75-6
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: TWXOQHRHGLZKFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.66
• 氢给体数：
  1.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  10-nitrosoanthracen-9-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以97%的产率得到10-imino-9(10H)-anthracenone
  参考文献：
  名称：

  Anthracenediols as reactive dienes in base-catalyzed cycloadditions: reduction-cycloaddition reactions of anthraquinones

  摘要：

  Anthraquinone is readily reduced to the hydroquinone (9,10-anthracenediol), which under basic conditions serves as a reactive diene for cyloaddition purposes. Catalytic hydrogenation in pyridine solvent provides convenient access to this species, and efficient reactions occur with dienophiles in situ, provided that they are sufficiently reactive. Thus N-methylmaleimide (NMM) gives the bicyclic bridgehead diol in near quantitative yield when the H2/Pd reduction of anthraquinone is carried out in pyridine containing 1 equiv of NMM. Fumaronitrile and maleonitrile similarly give high yields in stereospecific reactions, with the dienophile geometry retained in the cycloadduct. Less reactive dienophiles suffer competitive reduction. Dimethyl fumarate in situ gives cycloadduct (stereospecifically) in only 35-60% yield, with the remainder of the dienophile reduced to dimethyl succinate. Stepwise reduction followed by addition of dienophile leads to a higher yield in this and related reactions. The benzologues 5,12-naphthacenedione and 6,13-pentacenedione undergo analogous reactions with NMM, leading to novel bridgehead diols. The monimine of anthraquinone exhibits NMR features attributed to syn/anti isomerism. Under neutral or mildly basic conditions, the aromatic protons on the ring proximal to the NH are clearly distinguished (500 MHz) from those on the distal ring. The addition of acid causes rapid syn/anti NH exchange leading to time averaged symmetry. This imine behaves similarly to anthraquinone in the reduction/cycloaddition sequence. For example, with NMM in situ an essentially quantitative yield of the novel bridgehead amino alcohol adduct is obtained. Related benzologue reactions and attempts to extend the sequence to the oxime and methylene analogues of anthraquinone are described. Base-catalyzed ring opening of the cycloadduct of NMM/anthracenediol leads to a novel retro-bis-aldol reaction, resulting in the formation of anthraquinone and N-methylsuccinimide.

  DOI：

  10.1021/jo00004a009
• 作为产物：
  描述：

  蒽醌 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以65 %的产率得到10-nitrosoanthracen-9-ol
  参考文献：
  名称：

  通过电氧化脱肟从肟生成羰基化合物

  摘要：

  开发了一种电化学方案，用于从肟生成具有优异官能团相容性的羰基化合物。机理实验研究支持这样的观点，即可能涉及肟的电氧化途径，其中水可以充当氧亲核试剂和最终羰基化合物的氧源。

  DOI：

  10.1021/acs.joc.3c02631

文献信息

• Synthesis, antiproliferative activity and inhibition of tubulin polymerization by anthracenone-based oxime derivatives
  作者：Georg Surkau、Konrad J. Böhm、Klaus Müller、Helge Prinz

  DOI：10.1016/j.ejmech.2010.04.019

  日期：2010.8

  order to evaluate their antiproliferative activity. Several investigated compounds displayed strong antiproliferative activity against K562 leukemia cells and proved to be strong inhibitors of tubulin polymerization. In this context, anthracenone-based oxime ethers and -esters are considered to contribute to the development of novel antiproliferative drugs, based on tubulin interaction.

  为了评估它们的抗增殖活性，合成了一系列基于蒽醌的肟醚和酯。几种研究过的化合物显示出对K562白血病细胞的强抗增殖活性，并被证明是微管蛋白聚合的强抑制剂。在这种情况下，基于微管蛋白的相互作用，基于蒽醌的肟醚和-酯被认为有助于新型抗增殖药的开发。
• Photonitrosation promoted by enhanced acidity of singlet-state phenols
  作者：Yuan L. Chow、Zheng Zhi Wu

  DOI：10.1021/ja00297a045

  日期：1985.5

  Nitrosation des naphtol-1 et -2, de l'allyl-2 naphtol-1 de l'anthracenol-1 et de l'anthracenol-9 par reaction avec la dimethylnitrosoamine. Obtention de quinone mnonooximes. Mecanisme

  Nitrosation desnaphtol-1 et -2, de l'allyl-2naphtol-1 de l'anthracenol-1 et de l'anthracenol-9 par 反应 avec la 二甲基亚硝胺。获得醌二肟。机制
• Light-induced self-nitrosation of polycyclic phenols with nitrosamine. Excited state proton transfer
  作者：Yuan L. Chow、Zheng Zhi Wu

  DOI：10.1021/ja00251a034

  日期：1987.8

  Photoexcitation of polycyclic phenols in the presence of N-nitrosodimethylamine caused the self-nitrosation of the phenols to give 1,2- or 1,4-quinone monooximes. With use of naphthols as models the key step of the photonitrosation was shown to be a dual sensitization process from the lowest singlet excited state of naphthols by proton transfer followed by energy migration within an exciplex to cause

  在 N-亚硝基二甲胺的存在下，多环酚的光激发导致酚的自亚硝化产生 1,2- 或 1,4-醌单肟。使用萘酚作为模型，光亚硝化的关键步骤被证明是从萘酚的最低单线激发态通过质子转移的双重敏化过程，然后是激基复合物中的能量迁移，导致已知的亚硝胺均裂；假定所得自由基物种经历萘酚的亚硝化。激发态质子转移 (ESPT) 反应的关键要求是通过一般碱（例如水和 TEA）淬灭光亚硝化作​​用来建立的，淬灭速率常数接近这些碱的萘酚荧光的淬灭速率常数。
• THE POLAROGRAPHY OF THE MONOXIMES AND DIOXIMES OF BENZOQUINONE, NAPHTHOQUINONE, AND ANTHRAQUINONE
  作者：R. M. Elofson、J. G. Atkinson

  DOI：10.1139/v56-002

  日期：1956.1.1

  The polarographic behavior of the monoximes and dioximes of 1,4-benzoquinone, 1,4-naphthoquinone, 1,2-naphthoquinone, and 9,10-anthraquinone has been investigated in the pH range 3 to 14. All of the compounds produce well-defined polarographic reduction waves which can be used for analytical purposes. Polarographic evidence indicates that the monoximes and the dioximes exhibit tautomerism.

  对1,4-苯醌，1,4-萘醌，1,2-萘醌和9,10-蒽醌的单肟和二肟化合物在pH 3至14范围内进行了极谱行为研究。所有化合物都产生明确的极谱还原波，可用于分析目的。极谱证据表明，单肟和二肟化合物表现出互变异构体。
• Rydon et al., Journal of the Chemical Society, 1957, p. 1900,1904
  作者：Rydon et al.

  DOI：——

  日期：——