6-formyl-1,4-naphthoquinone | 76916-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-formyl-1,4-naphthoquinone
• 英文别名: 5,8-Dioxonaphthalene-2-carbaldehyde
• CAS: 76916-90-0
• 化学式: C₁₁H₆O₃
• 分子量: 186.167
• InChiKey: DZIARLVMDHKVDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 6-formyl-1,4-naphthoquinone 、 足球烯 以 甲苯 为溶剂， 反应 18.0h， 以22%的产率得到N-methyl-2'-[6(1,4-naphthoquinonyl)]pyrrolidino[2',4':1,2][60]fullerene
  参考文献：
  名称：

  [60]Fullerene Adducts with Improved Electron Acceptor Properties

  摘要：

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.

  DOI：

  10.1021/jo0003753
• 作为产物：
  描述：

  6-(Hydroxymethyl)-4a,5,8,8a-tetrahydronaphthalene-1,4-dione 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 6-formyl-1,4-naphthoquinone
  参考文献：
  名称：

  A Diene Synthesis of Quinone Aldehydes

  摘要：

  Cycloaddition of 2-(hydroxymethyl)-l,3-butadiene with representative quinones occurs readily in refluxing toluene. Oxidative dehydrogenation of the resulting cycloadduct with activated manganese dioxide in refluxing benzene affords quinone aldehydes in good to excellent overall yield.

  DOI：

  10.1080/00397919208019067

文献信息

• A pentacene intermediate via formal intramolecular photoredox of a 6,13-pentacenequinone in aqueous solution
  作者：Yunyan Hou、Peter Wan

  DOI：10.1139/v07-117

  日期：2007.12.1

  photolysis of 4 in acidic aqueous solution (pH < 3) resulted in a clean intramolecular photoredox reaction, via an enol intermediate, to give 10 (green compound; Φ ~ 0.2 at pH 1), which was too reactive for isolation or trapping by standard ArOH trapping agents such as acetic anhydride. These reactions may be viewed as a one-way photochemical intramolecular “redox switch” from quinone to hydroquinone

  我们实验室发现的芳香酮在水溶液中的正式分子内光氧化还原反应（或串联光互变异构化）已扩展到许多苯醌。特别是，我们对光氧化还原反应是否可以应用于 2-(羟甲基)-6,13-​​并五苯醌 (4) 感兴趣，这将产生 2-甲酰基-6,13-​​二羟基并五苯 (10)，从而提供一种合成并五苯衍生物的光化学方法。虽然许多苯并苯醌表现出一系列的光氧化还原反应性，但 4 在酸性水溶液（pH < 3）中的光解导致分子内光氧化还原反应，通过烯醇中间体，产生 10（绿色化合物；Φ ~ 0.2，pH 1 )，它的反应性太强，无法通过标准的 ArOH 捕集剂（如乙酸酐）进行分离或捕集。
• Direct electrochemical synthesis of quinones from simple aromatics and heteroaromatics
  作者：Ling Zhang、Youtian Fu、Lei Yang、Liming Cao、Junjun Yi、Maolin Sun、Ruihua Cheng、Yueyue Ma、Jinxing Ye

  DOI：10.1039/d3cc01661g

  日期：——

  of quinones through direct oxidation of widely accessible arenes and heteroarenes under mild conditions. A variety of quinones and hetero quinones were prepared with moderate to good yields, without the involvement of the pre-functionalized substrates. In addition, this atom economic method also exhibits wide functional group tolerance, including C(sp2)–I bond, ester, aldehyde, and OTf groups. This

  我们开发了一种电化学策略，通过在温和条件下直接氧化广泛可及的芳烃和杂芳烃来合成醌。在不涉及预功能化底物的情况下，以中等到良好的收率制备了各种醌和杂醌。此外，这种原子经济学方法还表现出广泛的官能团耐受性，包括 C(sp 2 )–I 键、酯、醛和 OTf 基团。这种合成方法为 C(sp 2 )–H 键的转化提供了一种直接的原子经济方法。
• [60]Fullerene Adducts with Improved Electron Acceptor Properties
  作者：Beatriz M. Illescas、Nazario Martín

  DOI：10.1021/jo0003753

  日期：2000.9.1

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.
• A Diene Synthesis of Quinone Aldehydes
  作者：Russell A. Cormier、John S. Connolly、Libbie S. Pelter

  DOI：10.1080/00397919208019067

  日期：1992.8

  Cycloaddition of 2-(hydroxymethyl)-l,3-butadiene with representative quinones occurs readily in refluxing toluene. Oxidative dehydrogenation of the resulting cycloadduct with activated manganese dioxide in refluxing benzene affords quinone aldehydes in good to excellent overall yield.