4-hydroxy-3-(2-methylpropyl)naphthalene-1,2-dione | 62830-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-3-(2-methylpropyl)naphthalene-1,2-dione
• 英文别名: 2-hydroxy-3-isobutyl-[1,4]-naphthoquinone；2-hydroxy-3-isobutylnaphthalene-1,4-dione；2-hydroxy-3-isobutyl-1,4-naphthoquinone；NSC 26654；2-hydroxy-3-isobutyl-[1,4]naphthoquinone；2-Hydroxy-3-isobutyl-[1,4]naphthochinon
• CAS: 62830-53-9
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: UASBUFXONXNWEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(2-methylpropyl)naphthalene-1,2-dione 在 sodium acetate 、 lead dioxide 、 溶剂黄146 作用下， 生成 2-isobutyl-3-(6-isobutyl-5-oxo-5,6-dihydrobenzo[a]phenazin-6-yloxy)naphthalene-1,4-dione
  参考文献：
  名称：

  Quinonoid and phenazine compounds: Synthesis and evaluation against H37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis

  摘要：

  Several quinonoid and phenazine compounds were synthesized in moderate to high yields and showed activity against H(37)Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis. The cytotoxity of the compounds were evaluated against human peripheral blood mononuclear cells (PBMC) and these substances emerge as promising antitubercular prototypes. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.026
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 1,4-二氧六环 、 sodium carbonate 、 copper(II) sulfate 作用下， 生成 4-hydroxy-3-(2-methylpropyl)naphthalene-1,2-dione
  参考文献：
  名称：

  Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3212

  摘要：

  DOI：

文献信息

• A New Method to Prepare 3-Alkyl-2-hydroxy-1,4-naphthoquinones: [nl]Synthesis of Lapachol and Phthiocol
  作者：[nl]Vitor Ferreira、Sabrina Ferreira、David Rodrigues da Rocha、José Carneiro、Wilson Santos

  DOI：10.1055/s-0030-1260771

  日期：2011.7

  In this article a mild, simple, safe, and chemoselective synthesis and reduction of o-quinone methides to the corresponding 3-alkyl-2-hydroxy-1,4-naphthoquinones, compounds with interesting biological activity, mediated by the formic acid-water system is described. This new one-pot methodology was applied to the synthesis of lapachol and constitutes an efficient and inexpensive alternative for the preparation of this natural bioactive compound

  本文介绍了一种温和、简单、安全且化学选择性强的合成与还原邻醌甲烷为相应的3-烷基-2-羟基-1,4-萘醌的方法，这些化合物具有有趣的生物活性，通过甲酸-水体系介导。这种新的一锅法方法应用于合成拉帕醇，为制备这种天然生物活性化合物提供了一种高效且经济的替代方案。
• Organocatalytic Enantioselective Michael‐Aldol[3+2] Annulation for the Synthesis of Nitro‐Methanobenzo[7] annulenes
  作者：Yang Zhang、Jin‐Yu Liu、Xiao‐Hai Zhang

  DOI：10.1002/ejoc.202100974

  日期：2021.9.21

  An enantioselective Michael-Aldol[3+2] annulation via bifunctional thiourea catalysis has been reported, and a series of nitro-methanobenzo[7]annulenes with potential biological activities were synthesized in good yields with excellent enantio- and diastereoselectivities.

  已经报道了通过双功能硫脲催化的对映选择性 Michael-Aldol[3+2] 环化，并以良好的收率合成了一系列具有潜在生物活性的硝基甲烷苯并 [7] 环烯，并具有优异的对映选择性和非对映选择性。
• On the Oxidation of 2-Hydroxy-1,4-naphthoquinone Derivatives with Alkaline Potassium Permanganate^1,2
  作者：Samuel C. Hooker

  DOI：10.1021/ja01298a030

  日期：1936.7
• 21. Syntheses in the naphthalene series. Part II. 3-Hydroxy-2-alkyl-1 : 4-naphthaquinones
  作者：Gabra Soliman、Albert Latif

  DOI：10.1039/jr9440000055

  日期：——
• Introduction of organic radicals into quinones
  申请人：FIESER LOUIS F

  公开号：US02398418A1

  公开（公告）日：1946-04-16