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2-羟基-1,4-萘醌 | 83-72-7

2-羟基-1,4-萘醌
Lawsone
83-72-7
C10H6O3
174.152842998505
如需查看该化合物的详细结构式,mol文件,smile,InChi 请点击:2-羟基-1,4-萘醌结构式
6755
2-羟基-1,4-萘醌价格
简介
Lawsone 是一种萘醌染料,从 Lawsonia inermis 的叶片中分离得到,具有抗菌和抗氧化活性。
名称和标识符
MDL MFCD00001678
InChIKey CSFWPUWCSPOLJW-UHFFFAOYSA-N
Inchi 1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H
SMILES O=C1C2C(=CC=CC=2)C(=O)C(O)=C1
BRN 1565260
别名信息
- 中文别名 -
  • 2-羟基-1,4-萘醌
  • 2-羟基-1,4萘醌
  • 2-Hydroxy-1,4-naphthoquinone 2-羟基-1,4-萘醌
  • 2-Hydroxy-1,4-naphthoquinone,certified 标准品
  • 劳松黄
  • 2-羟基,4-萘二酮
  • 2-羟基-1,4-萘二酮
  • 2-羟基对萘醌
  • 劳索酮
  • 散沫花醌
  • 散沫花素
  • 指甲花醌
- 英文别名 -
  • 2-Hydroxynaphthalene-1,4-dione
  • C.I. 75480~Lawsone
  • lawsone (2-hydroxy-1,4-naphthoquinone)
  • Natural Orange 6
  • 2-Hydroxy-1,4-naphthoquinone
  • C.I. 75480
  • Lawsone
  • 2-Hydroxy-1,4-naphoquinone
  • 2-Hydroxy-1.4-naphthoquinone
  • LAWSONE(P)
  • LAWSONE(RG)
  • 2-Hydroxy-1,4-naphthalenedione
  • 2-Hydroxy-p-naphthoquinone
  • Natural orange 6
  • 2-Hydroxynaphthoquinone
  • Henna
  • Mehendi
  • Mendi
  • Lawson
  • HANA
  • Flower of paradise
  • C.I. Natural Orange 6
  • 1,4-Naphthalenedione, 2-hydroxy-
  • Lawsonia alba
  • Henna leaves
  • 1,4-Naphthoquinone, 2-hydroxy-
  • 2-hydroxy-1,4-dihydronaphthalene-1,4-dione
  • 2-HYDROXY-
  • 1,4-Naphthoquinone, 2-hydroxy- (6CI, 8CI)
  • 2-Hydroxy-1,4-naphthalenedione (ACI)
  • 1,4-Dihydro-1,4-dioxo-2-hydroxynaphthalene
  • 2-Hydroxy-1,4-dihydronaphthalene-1,4-dione
  • Flower of Paradise
  • Henna (dye)
  • NSC 27285
  • NSC 52500
  • NSC 8625
  • Pakarli
  • Q 0
  • Quino Power 20
  • Quino Power LSN
  • Quinoexter 2014
  • Quinoexter QE 2014
  • Hana
  • 2-hydroxy-1,4-naphthalenedione
  • 2-hydroxy-1,4-naphthoquinone
  • 2-HYDROXYNAPHTHOQUINONE
物化性质
实验特性
LogP 1.50750
PSA 54.37000
Merck 5393
折射率 1.5036 (estimate)
水溶性 2 g/L (20 ºC)
沸点 339.9°C at 760 mmHg
熔点 192-195 °C (dec.) (lit.)
闪点 192
溶解度 less than 1 mg/mL at 66° F (NTP, 1992)
颜色与性状 亮黄色棱状结晶。
稳定性 Stable. Combustible. Incompatible with strong oxidizing agents.
溶解性 溶于水和冰醋酸
色指数 75480
密度 1.2346 (rough estimate)
计算特性
精确分子量 174.03200
氢键供体数量 1
氢键受体数量 3
可旋转化学键数量 0
同位素质量 174.031694
重原子数量 13
复杂度 291
同位素原子数量 0
确定原子立构中心数量 0
不确定原子立构中心数量 0
确定化学键立构中心数量 0
不确定化学键立构中心数量 0
共价键单元数量 1
疏水参数计算参考值(XlogP) 0.9
互变异构体数量 3
表面电荷 0
拓扑分子极性表面积 54.4
分子量 174.15
国际标准相关数据
EINECS 6248
海关数据
海关编码 2914690090
海关数据

中国海关编码:

2914690090

概述:

2914690090 其他醌. 增值税率:17.0% 退税率:9.0% 监管条件:无 最惠国关税:5.5% 普通关税:30.0%

Summary:

2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

合成路线

合成路线:1 步

参考文献:
Example of the reaction at the solid-liquid interface: oxidation of naphthalenediols by potassium superoxide
Vidril-Robert, Daniele; et al, Tetrahedron Letters, 1984, 25(5), 529-32

合成路线:1 步

参考文献:
Reaction of 1,4-naphthoquinone α-oxide with hydrochloric and hydrobromic acids
Bobrov, A. I.; et al, Ukrainskii Khimicheskii Zhurnal (Russian Edition), 1979, 45(9), 900-1

合成路线:1 步

反应条件:
参考文献:
Oxidation of cyclic ketones catalyzed by polyethylene glycol and rhenium carbonyl under basic and exceptionally mild conditions
Osowska-Pacewicka, Krystyna; et al, Journal of Organic Chemistry, 1988, 53(4), 808-10

合成路线:1 步

反应条件:
参考文献:
2-Hydroxy-1,4-naphthoquinone
Fieser, L. F.; et al, Organic Syntheses, 1941, 21, 56-9

合成路线:1 步

反应条件:
参考文献:
Oxidative and oxidative-hydrolytic transformations of organic molecules. IV. Oxidative-hydrolytic changes of 2-methyl-1,4-naphthoquinone oxide
Shchukina, L. A.; et al, Zhurnal Obshchei Khimii, 1949, 19, 183-92

合成路线:1 步

反应条件:
参考文献:
Design, synthesis and activity of BBI608 derivatives targeting on stem cells
Zhou, Qifan; et al, European Journal of Medicinal Chemistry, 2018, 151, 39-50

合成路线:1 步

反应条件:
参考文献:
Production method of 2-hydroxynaphthoquinone-1,4
, Poland, , ,

合成路线:1 步

反应条件:
参考文献:
Discovery of juglone and its derivatives as potent SARS-CoV-2 main proteinase inhibitors
Cui, Jiahua ; et al, European Journal of Medicinal Chemistry, 2021, 225,

合成路线:1 步

反应条件:
参考文献:
Reactivity of potassium superoxide in heterogeneous phase. Oxidation of naphthalenediols to hydroxynaphthoquinones
De Min, Martine; et al, Tetrahedron, 1992, 48(10), 1869-82

合成路线:1 步

反应条件:
参考文献:
Activated zeolites and heteropolyacids: an efficient catalysts for the synthesis of triacetoxyaromatic precursors of hydroxyquinones
Hadjila, Dokari; et al, Asian Journal of Chemistry, 2013, 25(11), 6112-6116

合成路线:1 步

反应条件:
参考文献:
Reactions of N-sulfinylarylamines with 1,4-benzoquinone and 1,4-naphthoquinone: synthesis of N-arylsulfinamoyl quinones and their hydrolysis to hydroxyquinones
Amarasekara, Ananda S.; et al, Journal of the Chemical Society, 1995, (13), 1653-8

合成路线:1 步

反应条件:
参考文献:
Supported metalated phthalocyanine as catalyst for oxidation by molecular oxygen. Synthesis of quinones and carbonyl compounds
Villemin, Didier; et al, Synthetic Communications, 2002, 32(10), 1501-1515

合成路线:1 步

反应条件:
参考文献:
Regiospecific synthesis of hydroxyquinones and related compounds from 3-tert-butoxycyclobutene-1,2-dione
Heerding, Julia M.; et al, Journal of Organic Chemistry, 1991, 56(12), 4048-50

合成路线:1 步

反应条件:
参考文献:
Selective oxidation of 2-naphthol to 2-hydroxy-1,4-naphthoquinone with hydrogen peroxide catalyzed by 5,10,15,20-tetrakis(p-sulfonatophenyl)porphinatomanganese(III) chloride in aqueous solution.
Hassanein, M.; et al, Catalysis Communications, 2017, 97, 134-137

合成路线:1 步

反应条件:
参考文献:
Oxidation of naphthol with hydroperoxide catalyzed by metalloporphyrins. (II) Mechanism for preparation of 2-hydroxy-1,4-naphthaqinone
Yan, Yan; et al, Gaodeng Xuexiao Huaxue Xuebao, 2000, 21(1), 108-111

合成路线:1 步

反应条件:
参考文献:
Synthesis and antioxidant activity of novel series of naphthoquinone derivatives attached to benzothiophene moiety
Gouda, Moustafa A.; et al, Medicinal Chemistry (Los Angeles, 2013, 3(2), 228-232

合成路线:1 步

反应条件:
参考文献:
One-pot Synthesis of 2-Hydroxy-1,4-Naphthoquinone (Lawsone)
Sivakumar, Dhanavel; et al, Current Organic Synthesis, 2019, 16(3), 431-434

合成路线:1 步

参考文献:
Photochemical reactivity of α-sulfonyloxy enones: an easy method for arylation of 1,2-diketones
Feigenbaum, Alexandre; et al, Journal of Organic Chemistry, 1984, 49(13), 2355-60

合成路线:1 步

反应条件:
参考文献:
Quinones. VII. New routes to 2-hydroxy-1,4-naphthaquinones
Baillie, A. C.; et al, Journal of the Chemical Society [Section] C: Organic, 1966, (23), 2184-6

合成路线:1 步

反应条件:
参考文献:
Naphtho[2,3-b]furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
Li, Jimei; et al, Chemical Communications (Cambridge, 2019, 55(16), 2348-2351

合成路线:1 步

反应条件:
参考文献:
Synthesis of lawsone as dye
Li, Hong; et al, Advanced Materials Research (Durnten-Zurich, 2012, 550, 550-553

合成路线:1 步

反应条件:
参考文献:
Reactivity of potassium superoxide in heterogeneous phase. Oxidation of naphthalenediols to hydroxynaphthoquinones
De Min, Martine; et al, Tetrahedron, 1992, 48(10), 1869-82

合成路线:1 步

反应条件:
参考文献:
Synthesis of pharmacologically important naphthoquinones and anticancer activity of 2-benzyllawsone through DNA topoisomerase-II inhibition
Kumar, Balagani Sathish; et al, Bioorganic & Medicinal Chemistry, 2017, 25(4), 1364-1373

合成路线:1 步

反应条件:
参考文献:
Preparation of 2-hydroxy-1,4-naphthoquinone
, Japan, , ,

合成路线:1 步

反应条件:
参考文献:
An efficient C-C bond cleavage of 1,2-diols using tetraethylammonium superoxide
Singh, Krishna Nand; et al, Indian Journal of Chemistry, 2007, (8), 1347-1351

合成路线:1 步

参考文献:
Photochemistry of 2-arenesulfonyloxy-2-cyclohexenone. A convenient α-arylation of 1,2-cyclohexanediones
Feigenbaum, Alexander; et al, Tetrahedron Letters, 1979, (6), 537-40

合成路线:1 步

反应条件:
参考文献:
Aerobic oxidation of dihydroxyarenes substrates catalyzed by polymer-supported RuII-Pheox/silica-gel: a beneficial route for purification of industrial water
Abu-Elfotoh, Abdel-Moneim, Letters in Organic Chemistry, 2022, 19(3), 236-243

合成路线:1 步

反应条件:
参考文献:
Discovery of juglone and its derivatives as potent SARS-CoV-2 main proteinase inhibitors
Cui, Jiahua ; et al, European Journal of Medicinal Chemistry, 2021, 225,

合成路线:1 步

参考文献:
Oxidation of tetralones by potassium superoxide solubilized by crown ether
Hocquaux, Michel; et al, Tetrahedron Letters, 1984, 25(5), 533-6

合成路线:1 步

参考文献:
Photochemical reaction of 2-bromo-3-methoxy-1,4-naphthoquinone with silylenol ether - one-pot synthesis of polycyclic aromatic compounds
Maruyama, Kazuhiro; et al, Heterocycles, 1981, 16(11), 1963-74

合成路线:1 步

反应条件:
参考文献:
Spectral and antibacterial investigations of Er(III) Juglonates
Shinde, Vishwambhar P.; et al, International Journal of ChemTech Research, 2017, 10(3), 740-748

合成路线:1 步

反应条件:
参考文献:
Oxidation of cyclic ketones catalyzed by polyethylene glycol and rhenium carbonyl under basic and exceptionally mild conditions
Osowska-Pacewicka, Krystyna; et al, Journal of Organic Chemistry, 1988, 53(4), 808-10
相关文献
专业数据库参考
PubChemId 6755
参考资料
Reaxys RN 1565260
Beilstein 8,300
产品用途
用于染发剂、杀菌剂
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