6-acetyl-1,4-naphthaquinone | 51439-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-acetyl-1,4-naphthaquinone
• 英文别名: 6-acetyl-1,4-naphthoquinone；6-Acetyl-1,4-naphthochinon；6-Acetylnaphthalene-1,4-dione
• CAS: 51439-36-2
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: MJDSWBRCFIGVMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  6-acetyl-1,4-naphthaquinone 以 二甲基亚砜 为溶剂， 生成 1,3-dihydroxy-6-carboxyanthraquinone
  参考文献：
  名称：

  Cameron, Donald W.; Feutrill, Geoffrey I.; Patti, Antonio F., Australian Journal of Chemistry, 1980, vol. 33, # 7, p. 1805 - 1816

  摘要：

  DOI：
• 作为产物：
  描述：

  2-acetyl-5,8-dimethoxy-naphthalene 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以92%的产率得到6-acetyl-1,4-naphthaquinone
  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

• (1,5)-Acetyl shifts in cycloadducts derived from 2-acetyl-1,4-benzoquinones
  作者：Simon C. Cooper、Peter G. Sammes

  DOI：10.1039/c39800000633

  日期：——

  (1,5)-Acetyl shifts have been investigated in a number of cycloadducts prepared from 2-acetyl-1,4-benzoquinone and dienes, and it has been shown that the direction of migration depends on the nature of the diene substituents.

  在由2-乙酰基-1,4-苯醌和二烯制得的许多环加合物中，已经研究了（1,5）-乙酰基转移，并且已表明迁移方向取决于二烯取代基的性质。
• 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。
• Cooper, Simon C.; Sammes, Peter G., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2407 - 2414
  作者：Cooper, Simon C.、Sammes, Peter G.

  DOI：——

  日期：——
• COOPER S. C.; SAMMES P. G., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 13, 633-634
  作者：COOPER S. C.、 SAMMES P. G.

  DOI：——

  日期：——
• CAMERON D. W.; FEUTRILL G. I.; PATTI A. F., AUSTRAL. J. CHEM., 1980, 33, NO 8, 1805-1816
  作者：CAMERON D. W.、 FEUTRILL G. I.、 PATTI A. F.

  DOI：——

  日期：——