1-(1,4-二羟基萘-2-基)乙酮 | 40420-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(1,4-二羟基萘-2-基)乙酮
• 英文名称: 2-acetylnaphthalene-1,4-diol
• 英文别名: 2-acetyl-1,4-dihydroxynaphthalene；1-(1,4-dihydroxynaphthalen-2-yl)ethan-1-one；NSC111552；1,4-Dihydroxy-2-acetyl-naphthalin；1-(1,4-Dihydroxy-2-naphthyl)ethanone；1-(1,4-dihydroxynaphthalen-2-yl)ethanone
• CAS: 40420-48-2
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: CKLPUCARSNJTSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  216-217 °C
• 沸点：
  434.7±30.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1,4-二羟基萘-2-基)乙酮 在 ammonium cerium (IV) nitrate 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 6.0h， 生成 1-(5-hydroxy-2-methoxy-2-methyl-2,3-dihydronaphtho[1,2-b]furan-4-yl)ethanone
  参考文献：
  名称：

  Anti-tyrosinase, antioxidant, and antibacterial activities of novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans

  摘要：

  Novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans (7a-k) were synthesized using ceric ammonium nitrate (CAN)-catalyzed formal [3 + 21 cycloaddition. Synthesized compounds were evaluated for their tyrosinase inhibitory, antioxidant, and antibacterial activities. A modified spectrophotometric method using L-DOPA as substrate was used to determine tyrosinase inhibitory activities, and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was used to evaluate antioxidant properties. Antibacterial activities against gram-negative Escherichia colt (KTC-1924) and gram-positive Staphylococcus aureus (KTC-1916) were evaluated using the disc diffusion technique. Of the synthesized compounds, 7b with a 4-acetyl and an electron-enriched dihydronaphthofuran ring showed the highest tyrosinase-inhibition activity (IC50 = 8.91 mu g/mL), which was comparable with that of standard kojic acid (IC50 = 10.16 mu g/ mL), potent antioxidant activity (IC50 = 3.33 mu g/mL), which was comparable with that of BHT (IC50 = 34.67 mu g/mL), and excellent antibacterial activities (MICs: 0.50 mu g/mL against E. coli and S. aureus strains). A mechanistic analysis of 7b demonstrated that its tyrosinase inhibitory activity was reversible and competitive. Compounds 7c and 7d showed potent antioxidant activities (IC50: 6.30 and 5.01 mu g/mL), and compound 7d also exhibited potent inhibitory activity against E. coli with a MIC of 0.5 mu g/mL. Furthermore, compounds 7a, 7e, 7f, and 7i showed potent antibacterial activities against S. aureus with MICs of 0.5 mu g/mL, which was comparable to that of ampicillin (MIC = 0.5 mu g/mL). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.025
• 作为产物：
  描述：

  1,4-二羟基萘 在 sodium hydroxide 、 三氟化硼 、 sodium hydrogensulfite 作用下， 生成 1-(1,4-二羟基萘-2-基)乙酮
  参考文献：
  名称：

  Quinones. I. The Syntheses of Acetyl-p-benzoquinone Derivatives and 2-Acetylnaphthoquinone

  摘要：

  DOI：

  10.1246/bcsj.34.300

文献信息

• Naphthalenyloxy substituted carboxylic acids
  申请人：Hoffmann-La Roche Inc.

  公开号：US04539419A1

  公开（公告）日：1985-09-03

  Compounds of the formula ##STR1## wherein R is hydrogen or lower alkyl, X is hydrogen or halogen, and A is the group ##STR2## wherein R.sub.1 is hydrogen, acyl or lower alkyl, R.sub.2 is hydrogen or lower alkyl, m is an integer from 2 to 4, n is an integer from 1 to 3, and t is an integer from 1 to 5, provided that R.sub.1 is adjacent to --(CH.sub.2).sub.m [O(CH.sub.2).sub.m ].sub.n O--, and, when R.sub.2 is hydrogen, salts thereof with pharmaceutically acceptable bases, are described. The compounds of formula I are useful as agents for the treatment of allergic conditions.

  式为##STR1##的化合物，其中R为氢或较低的烷基，X为氢或卤素，A为基团##STR2##，其中R.sub.1为氢、酰基或较低的烷基，R.sub.2为氢或较低的烷基，m为2至4的整数，n为1至3的整数，t为1至5的整数，前提是R.sub.1邻接于--(CH.sub.2).sub.m [O(CH.sub.2).sub.m ].sub.n O--，当R.sub.2为氢时，其与药用可接受碱的盐被描述。式I的化合物可用作治疗过敏症状的药物。
• Electroreductive Coupling of Phthalic Anhydrides with α,β-Unsaturated Carbonyl Compounds: Synthesis of 1,4-Dihydroxynaphthalenes
  作者：Naoki Kise、Shota Yamamoto、Toshihiko Sakurai

  DOI：10.1021/acs.joc.0c02000

  日期：2020.11.6

  Electroreductive coupling of phthalic anhydrides with α,β-unsaturated carbonyl compounds in the presence of TMSCl and subsequent treatment with 1 M HCl gave 1,4-dihydroxynaphthalenes and 2-methyl-2,3-dihydronaphthalene-1,4-diones.

  在TMCSI存在下，邻苯二甲酸酐与α，β-不饱和羰基化合物的电还原偶联，随后用1M HCl处理，得到1，4-二羟基萘和2-甲基-2，3-二氢萘-1，4-二酮。
• Über einige synthetische Naphtopyrone
  作者：H. Schmid、H. Seiler

  DOI：10.1002/hlca.19520350627

  日期：1952.8.1

  Es wird die Herstellung folgender neuer Chromone beschrieben: 2,3′-Dimethyl-[naphto-1′,2′ : 5,6-pyron-(4)], 2-Methyl-4′-methoxy-[naphto-1′,2′ : 6,5-pyron-(4)], 2-Methyl-[naphto-2′,3′ : 5,6-pvron-(4)] und 2-[Naphto-2′,3′ : 5,6-pyron-(4)]-carbonsäure.

  描述了以下新色酮的生产：2,3'-二甲基-[萘-1'，2'：5,6-吡喃酮-（4）]，2-甲基-4'-甲氧基-[萘-1 '，2'：6,5-吡喃酮（4）]，2-甲基-[naphto-2'，3'：5,6-pvron-（4）]和2- [naphto-2'，3' ：5，6-吡喃酮（4）]羧酸。
• Non-Catalyzed Thermal Reactions of Acylquinones with Allylstannanes
  作者：Kazuhiro Maruyama、Yoshihiro Matano

  DOI：10.1246/bcsj.62.3877

  日期：1989.12

  Thermal reactions of acylquinones with allylstannanes in benzene afforded several kinds of product after column chromatography on silica gel; acyl allyl quinones, acyl allyl epoxy quinones, cyclopentanoid compounds including stannyl moiety, allyl hydroxy quinones, acyl hydroquinones, and acyl allyl hydroquinones. The main product comprises cyclopentanoid compounds, which are novel [2+3] cyclo adducts with 1,2-migration of trialkylstannyl moiety. Spectroscopic examinations (1H NMR and Vis-UV) enabled us to confirm the reaction pathways that four types of precursors were initially generated via polarized tight pair and inverted to isolated products during purification by column chromatography. Similar reactions in acetonitrile showed a remarkable difference in the reactivity, that is, acyl allyl quinones and the corresponding hydroquinones are obtained, but the [2+3] cyclo adducts are not produced at all. From 1H NMR examination, it was confirmed that three types of precursor are generated via solvent separated ion pairs at the initial stage. The rather strong reactivity of acylquinones towards allylstannanes will be due to electron withdrawing ability of acyl group.

  酰基喹诺酮与烯丙基锡在苯中的热反应经过硅胶柱层析后产生了几种产品；包括酰基烯丙基喹诺酮、酰基烯丙基环氧喹诺酮、含锡基团的环戊烷类化合物、烯丙基羟基喹诺酮、酰基羟基喹诺酮和酰基烯丙基羟基喹诺酮。主要产品是环戊烷类化合物，它们是新型的 [2+3] 环加成物，具有三烷基锡基团的 1,2-迁移。通过光谱学检查（1H NMR 和 Vis-UV），我们确认了反应途径，四种前体最初通过极化紧配对生成，并在柱层析纯化过程中转化为孤立的产品。在乙腈中的类似反应显示出明显的反应性差异，即生成酰基烯丙基喹诺酮及其对应的羟基喹诺酮，但完全不产生 [2+3] 环加成物。从 1H NMR 检查中确认，三种类型的前体在初始阶段通过溶剂分离离子对生成。酰基喹诺酮对烯丙基锡的较强反应性将是由于酰基的电子吸引能力。
• An Annulation Reaction to Naphthalene-1,4-diols Using Dimethyl Phthalide-3-phosphonates.
  作者：Mitsuaki WATANABE、Hitoshi MORIMOTO、Kayoko NOGAMI、Saori IJICHI、Sunao FURUKAWA

  DOI：10.1248/cpb.41.968

  日期：——

  A regioselective annulation to naphthalene ring systems from dimethyl phthalide-3-phosphonates and electron-deficient olefins is described.

  描述了一种从二甲基苯二酸酯-3-膦酸酯和电子缺乏的烯烃中选择性合成萘环体系的区域选择性环化反应。