2-Hydroxy-6-methoxynaphthalene-1,4-dione | 6223-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Hydroxy-6-methoxynaphthalene-1,4-dione
• 英文别名: 6-methoxylawsone；2-hydroxy-6-methoxy-1,4-naphthalenedione；6-methoxy-2-hydroxynaphthalene-1,4-dione；2-hydroxy-6-methoxy-[1,4]naphthoquinone；2-hydroxy-6-methoxyl-1,4-naphthoquinone；2-hydroxy-6-methoxy-1,4-naphthoquinone
• CAS: 6223-31-0
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: RZMSKDLHMYQJGS-UHFFFAOYSA-N

物化性质

• 熔点：
  197-200 °C (decomp)
• 沸点：
  412.4±45.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2914690090
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-6-methoxynaphthalene-1,4-dione 在 C₂₈H₂₆F₆N₄S 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 1.0h， 生成 (R)-methyl 3-(1,4-dihydro-2-hydroxy-6-methoxy-1,4-dioxonaphthalen-3-yl)butanoate
  参考文献：
  名称：

  Organocatalyzed Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinone to β,γ-Unsaturated α-Ketophosphonatesθ

  摘要：

  By employing a cinchonine-based thiourea as catalyst, highly enantioselective Michael addition reactions of 2-hydroxy-1,4-naphthoquinone to beta,gamma-unsaturated alpha-ketophosphonates were realized. The reaction afforded the corresponding beta-substituted carboxylates in excellent yields with high levels of enantioselectivities (94 -> 99% cc) upon quenching the generated parent structures with DBU and MeOH as a second nucleophile.

  DOI：

  10.1021/jo2002825
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 potassium tert-butylate 、 氧气 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以92.3%的产率得到2-Hydroxy-6-methoxynaphthalene-1,4-dione
  参考文献：
  名称：

  β-拉帕酮-monastrol杂种作为潜在抗癌剂的合成及生物学评估。

  摘要：

  设计和合成了一系列新颖的β-拉帕酮类似物，用monastrol的四氢嘧啶硫酮部分取代了β-拉帕酮的吡喃环。这些杂种对富含NQO1的细胞系（HepG2和A549）具有有效的抗增殖活性，而NQO1缺陷的细胞系（H596和LO2）对这些杂种不那么敏感。Dicoumarol部分抑制了这些化合物对A549细胞的活性，表明NQO1介导的生物还原的激活可能部分影响了抗增殖作用。NQO1分析和对接研究表明4j是NQO1的良好底物。此外，正如有关抗肿瘤活性的细胞机制研究所建议的那样，代表性化合物4j导致依赖NQO1产生ROS，然后氧化应激触发凋亡性细胞死亡。重要的是，在HepG2异种移植模型中4j显着抑制了癌症的生长，而没有明显的毒性，这表明4j作为有效的抗癌药物，值得进一步研究。

  DOI：

  10.1016/j.ejmech.2020.112594

文献信息

• Quinonoid compounds via reactions of lawsone and 2-aminonaphthoquinone with α-bromonitroalkenes and nitroallylic acetates: Structural diversity by C-ring modification and cytotoxic evaluation against cancer cells
  作者：Thekke V. Baiju、Renata G. Almeida、Sudheesh T. Sivanandan、Carlos A. de Simone、Lucas M. Brito、Bruno C. Cavalcanti、Claudia Pessoa、Irishi N.N. Namboothiri、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.ejmech.2018.03.079

  日期：2018.5

  Morita-Baylis-Hillman acetates and α-bromonitroalkenes have been employed in cascade reactions with lawsone and 2-aminonaphthoquinone for the one-pot synthesis of heterocycle fused quinonoid compounds. The reactions reported here utilized the 1,3-binucleophilic potential of hydroxy- and aminonaphthoquinones and the 1,2/1,3-bielectrophilic potential of bromonitroalkenes and Morita-Baylis-Hillman acetates

  Morita-Baylis-Hillman乙酸盐和α-溴硝基烯烃已用于与Lawone和2-氨基萘醌的级联反应，用于一锅合成杂环稠合的醌类化合物。此处报道的反应利用羟基和氨基萘醌的1,3-双亲核势以及溴硝基烯烃和Morita-Baylis-Hillman乙酸酯的1,2 / 1,3-双亲电势来合成吡咯和呋喃稠合的萘醌。对合成的化合物针对HCT-116（人类结肠癌细胞），PC3（人类前列腺癌细胞），HL-60（人类早幼粒细胞白血病细胞），SF295（人类胶质母细胞瘤细胞）和NCI-H460（人类肺癌细胞）进行了评估。并显示出抗肿瘤活性，IC50值低至<2μM。还针对OVCAR-8（卵巢）评估了选定的化合物，MX-1（乳腺癌）和JURKAT（白血病）细胞系。还使用非肿瘤细胞测定了评价的醌类的细胞毒性潜力，例如外周血单核（PBMC）和L929细胞。
• Ceric Ammonium Nitrate Mediated Cycloaddition of Hydroxyquinones with Alkenes for the One-Step Construction of Furoquinone Derivatives
  作者：Kazuhiro Kobayashi、Masako Mori、Tomokazu Uneda、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/cl.1996.451

  日期：1996.6

  A one-step formation of furoquinones, such as naphtho[2,3-b]furan-4,9-dione, naphtho[1,2-b]furan-4,5-dione, benzofuran-4,7-dione, and benzofuran-4,5-dione derivatives, by the ceric ammonium nitrate mediated [3+2] type cycloaddition of 2-hydroxy-1,4-naphthoquinones and 2-hydroxy-1,4-benzoquinones with alkenes or phenylacetylene is described.

  通过硝酸铈铵介导的 [3+2] 型环加成反应，将 2-羟基-1,4-萘醌和 2-羟基-1,4-苯醌与烯烃或苯基乙炔一步合成呋喃[2,3-b]并萘烷-4,9-二酮、呋喃[1,2-b]并萘烷-4,5-二酮、苯并呋喃-4,7-二酮和苯并呋喃-4,5-二酮衍生物的方法被报道。
• NIS-Induced Enone Difunctionalization for the Synthesis of Naphtho[2,3-<i>b</i> ]furan-4,9-diones
  作者：Yun Liu、Wen-Hui Ge、You-Quan Zhu、Hua-You Hu、Hui Fan、Yan-Hui Shi、Hui Wu

  DOI：10.1002/ejoc.201601291

  日期：2017.1.18

  3-b]furan-4,9-diones has been developed by N-iodosuccinimide (NIS)-induced enone difunctionalization with 2-hydroxy-1,4-naphthoquinones. This reaction involved sequential Michael addition, intramolecular oxidative cyclization and dehydrogenative aromatization to form new C–C and C–O bonds at the α and β positions of the enones. Various enones survived under the reaction conditions and the corresponding products

  萘并[2,3-b]呋喃-4,9-二酮的有效合成已通过N-碘代琥珀酰亚胺（NIS）诱导的烯酮双官能化与2-羟基-1,4-萘醌进行合成。该反应涉及连续的迈克尔加成、分子内氧化环化和脱氢芳构化，以在烯酮的 α 和 β 位置形成新的 C-C 和 C-O 键。各种烯酮在反应条件下幸存下来，并以中等至优异的收率获得相应的产物。
• Chiral (thio)phosphorodiamides as excellent hydrogen bond donor catalysts in the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquione to nitroolefins
  作者：Ronghua Wu、Xufang Chang、Aidang Lu、Youming Wang、Guiping Wu、Haibin Song、Zhenghong Zhou、Chuchi Tang

  DOI：10.1039/c1cc10797f

  日期：——

  A novel type of bidentate hydrogen bond donor catalysts based on (thio)phosphorodiamides catalophore has been developed for the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquione to nitroolefins, affording the corresponding adducts in high yields with excellent level of enantioselectivities (97- >99% ee).

  已经开发出了一种新型的基于（硫代）磷二酰胺基阴极的双齿氢键供体催化剂，用于将2-羟基-1,4-萘并醌不对称地迈克尔加成到硝基烯烃中，从而以高收率提供相应的加合物，同时具有出色的对映选择性（ 97-> 99％ee）。
• COMPOUND, COMPLEX, PREPARATION METHOD THEREOF, AND USE THEREOF
  申请人：JIANGSU OXIRANCHEM CO., LTD

  公开号：US20210395283A1

  公开（公告）日：2021-12-23

  The present disclosure provides a compound, a complex, a preparation method thereof, and a use thereof. The compound is represented by the following structural formula, in which R 1 to R 10 are the same or different and are each independently selected from hydrogen, a hydrocarbon group having a carbon number of C 1 to C 16 , a substituted hydrocarbon group, an alkoxy group, an alkylthio group, an alkylamino group, a haloalkylthio group, a halogen-substituted alkoxy group, a halogen-substituted alkylamino group, an aryloxy group, an arylthio group, arylamino group, a diphenylphosphino group, a halogen group, a nitro group, or a nitrile group. The complex of one embodiment of the present disclosure has a high catalytic effect, and can be used to prepare a highly branched, controllable, low molecular weight polymer with a high activity.

  本公开提供了一种化合物、一种配合物、其制备方法及其用途。所述化合物由以下结构式表示，其中R1至R10相同或不同，并且各自独立地选自氢、碳数为C1至C16的烃基、取代烃基、烷氧基、烷硫基、烷氨基、卤代烷硫基、卤代烷氧基、卤代烷氨基、芳氧基、芳硫基、芳香胺基、二苯膦基、卤素、硝基或腈基。本发明一个实施例的配合物具有高催化效果，可用于制备具有高活性的高度支化、可控、低分子量的聚合物。