2-乙酰基萘-1,4-二酮 | 5813-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-乙酰基萘-1,4-二酮
• 英文名称: 2-acetyl-1,4-naphthoquinone
• 英文别名: 2-acetylnaphthalene-1,4-dione
• CAS: 5813-57-0
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: LKDQLNOZQAMIOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：

  2-乙酰基萘-1,4-二酮 以 吡啶 、 甲醇 为溶剂， 生成 1,4-二氢蒽-9,10-二醇
  参考文献：
  名称：

  [1,5]和[1,2] 2-乙酰基-6-甲基-1,4-苯醌的Diels–Alder加合物中的乙酰基转移

  摘要：

  用吡啶-甲醇或乙酸酐处理Diels-Alder加合物4a-乙酰基-4a，5,8,8a-四氢-3-甲基-1，4-萘醌导致[1,5]乙酰基转移至3 -位置，然后可以将[1,2]乙酰基移至2位置（加合物编号）。

  DOI：

  10.1039/c39810000169
• 作为产物：
  描述：

  1,4-二羟基萘 在 sodium hydroxide 、 三氟化硼 、 potassium carbonate 、 sodium hydrogensulfite 、 silver(l) oxide 作用下， 以 苯 为溶剂， 生成 2-乙酰基萘-1,4-二酮
  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

• NEW SYNTHESIS OF METHYL 2-TRIORGANOSILYL-3-BUTENOATES AS A NEW SYNTHON OF 3-METHOXYCARBONYLALLYL ANION
  作者：Yoshinori Naruta、Hidemitsu Uno、Kazuhiro Maruyama

  DOI：10.1246/cl.1982.961

  日期：1982.7.5

  Methyl 2-triorganosilyl-3-butenoates, which are selectively obtained from the carboxylation of the corresponding allylsilanes via allylic aluminates, react with various kinds of electrophiles to give γ substituted (E)-α,β-unsaturated esters in highly regio and stereoselective manner with the aid of a Lewis acid.

  甲基2-三有机硅基-3-丁烯酸酯，通过烯丙基铝酸盐途径从相应的烯丙基硅烷进行羧基化选择性制备得到，在Lewis酸的辅助下，能高度区域选择性和立体选择性地与各种亲电试剂反应，生成γ取代的（E）-α,β-不饱和酯。
• 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。
• Addition of 2-tert-butyldimethylsilyloxythiophene to activated quinones: an approach to thia analogues of kalafungin
  作者：Margaret A. Brimble、Olivia Laita、James E. Robinson

  DOI：10.1016/j.tet.2006.01.040

  日期：2006.3

  afforded thiolactone benzofuran adducts 13 and 17, respectively, catalyzed by either InCl3 or Cu(OTf)2. Addition of 2-tert-butyldimethylsilyloxythiophene 2 to 3-acetyl-5-methoxy-1,4-naphthoquinone 12 afforded adduct 19 that underwent oxidative rearrangement to thiolactone pyranonaphthoquinone 20 using ceric ammonium nitrate in acetonitrile, thus providing a novel approach for the synthesis of a thia

  研究了2-叔丁基二甲基甲硅烷基氧基噻吩2与在C-2处带有吸电子乙酰基或碳甲氧基的1,4-醌的未催化反应。使用在C-2处带有酯基的1,4-醌8和9未观察到反应，而使用在C-2处带有乙酰基的1,4-醌10和11仅提供了低产率的甲硅烷氧基噻吩15和16由甲硅烷基氧噻吩被1，4-醌的亲电取代而产生。路易斯酸InCl 3，Cu（OTf）2和BF 3 ·Et 2的使用为了提高所需的环化反应的产率，对O进行了研究。BF 3 ·Et 2 O被证明是分别由1,4-萘醌9和11合成硫代内酯萘呋喃加合物14和18的最佳催化剂。2-叔丁基二甲基甲硅烷基氧基噻吩2与分别在C-2处带有甲氧基或乙酰基的1,4-苯醌8和10的反应分别得到InCl 3或Cu（OTf）催化的硫代内酯苯并呋喃加合物13和17。）2。将2-叔丁基二甲基甲硅烷基氧基噻吩2加到3-乙酰基-5-甲氧基-1,4-萘醌12中得到加合物19，该加合物19在
• Synthesis of (±)-eleutherin, (±)-isoeleutherin, and their demethoxy analogues. A novel synthetic approach
  作者：Yoshinori Naruta、Hidemitsu Uno、Kazuhiro Maruyama

  DOI：10.1039/c39810001277

  日期：——

  (±)-Eleutherin (1) and (±)-isoeleutherin (3) are prepared by intramolecular cyclization to the naphthopyrans of 2-acetyl-3-allyl-8-methoxy-1, 4-napthoquinone, which is itself obtained by the Lewis acid-mediated allylation of 2-acetyl-8-methoxy-1, 4-naphthoquinone (5) with allyltrimethylstannane (7).

  通过分子内环化成2-乙酰基-3-烯丙基-8-甲氧基-1、4-萘醌的萘并吡喃而制备（±）-伊卢色林（1）和（±）-异弹性蛋白（3），其本身是通过路易斯酸介导的2-乙酰基-8-甲氧基-1，4-萘醌（5）与烯丙基三甲基锡烷（7）的烯丙基化。
• In Vitro Inhibition of Hsp90 Protein by Benzothiazoloquinazolinequinones Is Enhanced in The Presence of Ascorbate. A Preliminary In Vivo Antiproliferative Study
  作者：Jaime A. Valderrama、David Ríos、Giulio G. Muccioli、Pedro Buc Calderon、Julio Benites

  DOI：10.3390/molecules25040953

  日期：——

  A series of benzo[g]benzothiazolo[2,3-b]quinazoline-7,12-quinones were prepared from 2-acylnaphthohydroquinones and 2-aminobenzothiazoles and were evaluated for their in vitro antiproliferative activity. After screening using the MTT reduction assay, their IC50 values were calculated on a panel of cancer cells (T24, DU-145, MCF-7). Current standard anticancer drugs were included as control, and their calculated IC50 values were 7.8 and 23.5 µM for 5-fluorouracil and tamoxifen, respectively. Non-cancer cells (AG1523) were included to assess cancer cell sensitivity and drug selectivity. Four members of the series, with IC50 values from 0.11 to 2.98 µM, were chosen for further assays. The selected quinones were evaluated regarding their effects on cancer cell proliferation (clonogenic assay) and on Hsp90 and poly(ADPribose)polymerase (PARP) protein integrity. The most active compound (i.e., 15) substantially inhibited colony forming unit (CFU) formation at 0.25 µM. In the presence of ascorbate, it induced an oxidative cleavage of Hsp90 but had no effect on PARP protein integrity. In an in vivo animal model, it discreetly increased the mean survival time (m.s.t.) of tumor-bearing mice. In light of these results, compound 15 represents a potential lead-molecule to be further developed.

  一系列苯并[g]苯并噻唑[2,3-b]喹唑啉-7,12-醌类化合物是通过2-酰基萘羟喹醌和2-氨基苯并噻唑反应制备的，并对它们的体外抗增殖活性进行了评估。通过MTT还原实验筛选后，在一系列癌细胞（T24、DU-145、MCF-7）中计算了它们的IC50值。当前标准的抗癌药物被包括为对照，5-氟尿嘧啶和他莫昔芬的计算IC50值分别为7.8和23.5微米。非癌细胞（AG1523）被包括以评估癌细胞的敏感性和药物选择性。系列中的四个成员，其IC50值从0.11到2.98微米不等，被选定进行进一步的实验。选定的醌类化合物被评估其对癌细胞增殖（克隆形成实验）以及对Hsp90和聚(ADP核糖)聚合酶（PARP）蛋白完整性的影响。最活性的化合物（即15号）在0.25微米下显著抑制了克隆形成单位（CFU）的形成。在抗坏血酸存在的情况下，它诱导了Hsp90的氧化裂解，但对PARP蛋白的完整性没有影响。在体内动物模型中，它轻微增加了携带肿瘤的小鼠的平均存活时间（m.s.t.）。鉴于这些结果，化合物15代表了一个有潜力进一步开发的先导分子。