6-乙基萘-1,4-二酮 | 17539-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-乙基萘-1,4-二酮
• 英文名称: 6-ethyl-1,4-naphthoquinone
• 英文别名: 6-ethylnaphthalene-1,4-dione
• CAS: 17539-30-9
• 化学式: C₁₂H₁₀O₂
• mdl: MFCD18448835
• 分子量: 186.21
• InChiKey: UVHMQBSPOCXMKB-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  348.5±42.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 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：

  2-acetyl-5,8-dimethoxy-naphthalene 在 palladium on activated charcoal 盐酸 、 ammonium cerium(IV) nitrate 、 氢气 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 0.25h， 生成 6-乙基萘-1,4-二酮
  参考文献：
  名称：

  Protein tyrosine kinase inhibitory properties of planar polycyclics obtained from the marine sponge Xestospongia cf. carbonaria and from total synthesis

  摘要：

  Nine related polycyclic quinones and hydroquinones of the halenaquinone class were isolated from two Indo-Pacific collections of the sponge Xestospongia cf. carbonaria. The halenaquinone family appears not to be of polyketide origin but can be biogenetically derived by the union of a sesquiterpene and a quinone. Four new metabolites were characterized including tetrahydrohalenaquinone B (8a), 14-methoxyhalenaquinone (9), xestoquinolide A (10), and xestoquinolide B (11). These were accompanied by five known compounds, halenaquinone (3), halenaquinol (4), halenaquinol sulfate (5), xestoquinone (6), and tetrahydrohalenaquinone A (7a). The new structures were established from 2D NMR data, and the absolute stereochemistry of the chiral centers in 7 and 8 was determined by the formation of 7b and 7c, the bis esters of O-methylmandelic acid. A series of polycyclic models of natural products 3 and 6 were synthesized and included 16-23. The more complex members of this group were assembled via a 4 + 2 cycloaddition between an o-quinodimethane and a functionalized enone. The marine natural products plus two known fungal metabolites, viridin (13) and wortmannin (14), along with halenaquinone synthetic model compounds, were each tested for their ability to inhibit the activity of pp60v-src protein tyrosine kinase (PTK). Halenaquinone and 14-methoxyhalenaquinone were the most potent with IC50 values <10 muM. The other compounds were either less potent or inactive, and a rationalization for this SAR (structure activity relationship) pattern is presented.

  DOI：

  10.1021/jo00070a023

文献信息

• Controlled reduction of aromaticity of alkylated polyaromatic compounds by selective oxidation using H₂WO₄, H₃PO₄ and H₂O₂: a route for upgrading heavy oil fractions
  作者：Ewa Nowicka、Meenakshisundaram Sankar、Robert L. Jenkins、David W. Knight、David J. Willock、Graham J. Hutchings、Manuel Francisco、Stuart H. Taylor

  DOI：10.1039/d1nj01986d

  日期：——

  H2O2 oxidant is applied to the selective oxidation of PAHs containing different lengths of substituent alkylated chain, and different numbers of rings in the fused aromatic core. For a model substrate of 2-ethylnaphthalene, using traditional organic solvents, aliphatic carbon was oxidized more readily compared to aromatic carbon. However, it was found that the oxidation to desired products can be specifically

  形成分馏残余物的重质原油馏分占当前烃储量的很大一部分。然而，用作化学品或燃料的加工残留物受到该材料高多芳烃含量的阻碍。通过有针对性的开环和保留烷基化链侧基来选择性降低芳香性是将烷基化多环芳烃 (PAH) 升级为更容易加工和更高价值的分子的关键要求。在本研究中，H 2 WO 4催化剂与 H 3 PO 4和 H 2 O 2 结合氧化剂用于选择性氧化含有不同长度取代基烷基化链和稠合芳核中不同环数的多环芳烃。对于 2-乙基萘的模型底物，使用传统有机溶剂，与芳族碳相比，脂肪族碳更容易被氧化。然而，发现氧化成所需产物可以特别控制，因为选择性受溶剂选择的指导，在乙腈中进行的反应仅在分子的芳族区域进行氧化。对于较大的聚芳烃分子，双相溶剂系统与 Aliquat 336 一起用作相转移剂。即使对于这种更复杂的反应体系，也获得了向相应烷基化开环化合物的高转化率。
• A Novel and Convenient Process for the Selective Oxidation of Naphthalenes with Hydrogen Peroxide
  作者：Feng Shi、Man Kin Tse、Matthias Beller

  DOI：10.1002/adsc.200600395

  日期：2007.2.5

  catalyst (Ru-PTC) system for the oxidation of naphthalene derivatives has been developed. Substituted 1,4-quinones are obtained in good selectivity and yield in water without the addition of any organic solvent and acid. By applying the optimized conditions the feed additive menadione (vitamin K3) is obtained from 2-methylnaphthalene with 64 % yield and 73 % selectivity.

  已经开发出用于氧化萘衍生物的实用的钌相转移催化剂（Ru-PTC）系统。在不添加任何有机溶剂和酸的情况下，在水中以良好的选择性和收率获得了取代的1,4-醌。通过应用优化的条件，可以以64％的收率和73％的选择性从2-甲基萘获得饲料添加剂甲萘醌（维生素K 3）。
• Selective Oxidation of Alkyl-Substituted Polyaromatics Using Ruthenium-Ion-Catalyzed Oxidation
  作者：Ewa Nowicka、Meenakshisundaram Sankar、Robert L. Jenkins、David W. Knight、David J. Willock、Graham J. Hutchings、Manuel Francisco、Stuart H. Taylor

  DOI：10.1002/chem.201405831

  日期：2015.3.9

  Ruthenium‐ion‐catalyzed oxidation of a range of alkylated polyaromatics has been studied. 2‐Ethylnaphthalene was used as a model substrate, and oxidation can be performed in either a conventional biphasic or in a monophasic solvent system. In either case the reaction rates and product selectivity are identical. The reaction products indicate that the aromatic ring system is oxidized in preference to

  已经研究了钌离子催化的一系列烷基化聚芳族化合物的氧化。使用2-乙基萘作为模型基质，可以在常规的双相或单相溶剂体系中进行氧化。在两种情况下，反应速率和产物选择性都是相同的。反应产物表明，芳族环系优先于烷基链被氧化。由于开发了定量NMR协议来确定脂肪族和芳香族质子的相对量，因此这种分析是可能的。从一组系统的基质中，我们表明，随着多环芳烃上烷基链取代基的长度增加，链保持与芳族系统连接的产物比例也随之增加。基于pyr和菲的较大的多芳烃体系，
• Process for preparation of 2-substituted-1,4-naphthoquinone
  申请人：NIPPON SHOKUBAI KAGAKU KOGYO CO. LTD.

  公开号：EP0430164A2

  公开（公告）日：1991-06-05

  A process for preparation of a 2-substituted-1,4-naphthoquinone which comprises oxidizing a 2-substituted naphthalene to obtain reaction products comprising a 2-substituted-1,4-naphthoquinone and a 6-substituted-1,4-naphthoquinone; adding a diene compound to the reaction products and heating the mixture to form a Diels-Alder reaction adduct between the diene compound and the 6-substituted-1,4-naphthoquinone in the reaction products; and separating the 2-substituted-1,4-naphthoquinone from the adduct.

  一种制备 2-取代的-1,4-萘醌的工艺，包括氧化 2-取代的萘，得到包括 2-取代的-1,4-萘醌和 6-取代的-1,4-萘醌的反应产物；向反应产物中加入二烯化合物并加热混合物，使二烯化合物与反应产物中的 6-取代-1,4-萘醌形成 Diels-Alder 反应加合物；以及从加合物中分离出 2-取代-1,4-萘醌。
• Sioda; Frankowska; Lobuzinska, Polish Journal of Chemistry, 2004, vol. 78, # 9, p. 1567 - 1573
  作者：Sioda、Frankowska、Lobuzinska、Fahidy

  DOI：——

  日期：——