2-cyclohexyl-3-methylnaphthalene-1,4-dione | 54812-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-cyclohexyl-3-methylnaphthalene-1,4-dione
• CAS: 54812-04-3
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: LCBYRVPQVPJEHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲萘醌 、 diethyl 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 在 tetrabutylammonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以70 %的产率得到2-cyclohexyl-3-methylnaphthalene-1,4-dione
  参考文献：
  名称：

  4-羟基喹唑啉的自由基加成和醌的烷基化通过 4-烷基-1,4-二氢吡啶的电致均裂

  摘要：

  报道了通过 4-烷基-1,4-二氢吡啶 (烷基-DHP) 的电诱导均裂形成以 C(sp 3 ) 为中心的自由基。所得烷基自由基与4-羟基喹唑啉或醌反应，得到2-烷基二氢喹唑啉酮或烷基化醌。在电解条件下，多种烷基 DHP 可用作通用的自由基前体。这种替代策略为在温和条件下构建C(sp 2 )-C(sp 3 )和C(sp 3 )-C(sp 3 )键提供了一种简单有效的途径。

  DOI：

  10.1055/a-1737-2765

文献信息

• Metal-, Photocatalyst-, and Light-Free, Late-Stage C–H Alkylation of Heteroarenes and 1,4-Quinones Using Carboxylic Acids
  作者：Daniel R. Sutherland、Marcos Veguillas、Conor L. Oates、Ai-Lan Lee

  DOI：10.1021/acs.orglett.8b02988

  日期：2018.11.2

  Contrary to the accepted convention, this work shows that Minisci-type C–H alkylation does not require any metal, photocatalyst, light, or prefunctionalization of the readily available and inexpensive carboxylic acids to proceed well under mild conditions. These mild conditions can be utilized for late-stage alkylations of complex molecules, including pharmaceutical compounds and light-sensitive compounds

  与公认的惯例相反，这项工作表明，Minisci型C–H烷基化不需要任何金属，光催化剂，光或易于获得的廉价羧酸的预官能化，即可在温和条件下顺利进行。这些温和的条件可用于复杂分子的后期烷基化，包括在光催化条件下降解的药物化合物和光敏化合物。
• Iron-Catalyzed Radical Methylation of Activated Alkenes with tert-Butanol as the Methyl Source
  作者：Zhengbao Xu、Rui Jia、Zhiwei Ma、Shouhao Cao、Liang Shen、Hongfang Ji

  DOI：10.1055/s-0039-1690193

  日期：2019.10

  A free-radical-initiated methylation/addition/cyclization of N-arylacrylamides and a methylation/addition/elimination of quinines have been developed in which t-BuOH is used as a methyl source. These reactions provide effective and selective methods for the synthesis of various methylated oxindoles and quinones in moderate to good yields.

  已经开发了 N-芳基丙烯酰胺的自由基引发的甲基化/加成/环化和奎宁的甲基化/加成/消除，其中使用 t-BuOH 作为甲基源。这些反应为以中等至良好的产率合成各种甲基化羟吲哚和醌提供了有效和选择性的方法。
• 나프토퀴논 유도체, 벤조퀴논 유도체 및 안트라센디온 유도체, 이의 용도 및 신규 제조방법
  申请人：Industry Academic Cooperation Foundation of Yeungnam University 영남대학교 산학협력단(220040363026) BRN ▼515-82-06574

  公开号：KR20180134632A

  公开（公告）日：2018-12-19

  본 발명은 나프토퀴논, 벤조퀴논 또는 안트라센디온 화합물과 다양한 사이클로알칸과의 구리-촉매 교차-탈수소화 커플링 반응을 이용한 퀴논 유도체 또는 안트라센디온 유도체의 신규한 제조방법, 이로 제조된 나프토퀴논 유도체, 벤조퀴논 유도체와 안트라센디온 유도체 및 이의 용도에 관한 것으로, 본 발명의 신규한 제조방법에 따르면, 한 단계로 나프토퀴논 유도체, 벤조퀴논 유도체 또는 안트라센디온 유도체를 제조할 수 있어 제조 효율을 향상시킬 수 있으며, 비용 및 시간을 절감할 수 있고, 본 발명에 따른 유도체들은 동물 의약품으로도 다양하게 활용될 수 있다.

  本发明涉及一种使用萘醌、苯醌或蒽醌化合物与各种环戊烷进行铜催化的交叉脱氢偶联反应制备醌衍生物或蒽醌衍生物的新方法，以及由此制备的萘醌衍生物、苯醌衍生物和蒽醌衍生物及其用途。根据本发明的新制备方法，可以一步制备萘醌衍生物、苯醌衍生物或蒽醌衍生物，从而提高制备效率，节约成本和时间，根据本发明的衍生物也可以广泛应用于动物药品领域。
• Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant
  作者：Jian Yang、Yu Dong、Shuai He、Zhi-Chuan Shi、Yu Wang、Ji-Yu Wang

  DOI：10.1016/j.tet.2019.130729

  日期：2019.12

  radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones. This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K3 and benzoquinone. Notably, antimalarial parvaquone was synthesized

  通过自由基反应机理，在过氧苯甲酸叔丁酯（TBPB）存在下，铋催化了醌的甲基化。特别地，在这种转化中，TBPB不仅用作有效的氧化剂，而且还用作绿色甲基源。而且，该方法也可以有效地扩展到醌的烷基化。该反应耐受一系列官能团，并制备了一系列维生素K 3和苯醌的衍生物。值得注意的是，通过该反应合成了抗疟原虫苯醌。
• Functionalization of saturated hydrocarbons in Gif-type systems using 2-methyl-1,4-naphthoquinone
  作者：Derek H.R. Barton、Béatrice M. Chabot、Bin Hu

  DOI：10.1016/0040-4039(96)00168-2

  日期：1996.3

  The reaction between cyclohexane and 2-methyl-1,4-naphthoquinone using hydrogen peroxide in the FeIIFeIV manifold gave the adduct in good yield. The same reaction was carried out with the FeIIIH2O2 system and gave also some 3-alkyl-2-methyl-1,4-naphthoquinone. The presence of FeII during the reaction showed that the FeIIFeIV manifold was again dominant.

  环己烷和2-甲基-1,4-萘醌之间的反应使用过氧化氢在铁II Fe IV歧管，得到的加合物以良好的收率。相同的反应用铁进行III H 2 ö 2系统，并且还给出了一些3-烷基-2-甲基-1,4-萘醌。Fe的存在II在反应过程中表明，铁II Fe IV歧管再次占主导地位。