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等级
purum
质量水平
方案
≥96.5% (HPLC)
表单
powder
mp
119-122 °C (lit.)
120-124 °C
官能团
ketone
SMILES字符串
O=C1C=CC(=O)c2ccccc12
InChI
1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
InChI key
FRASJONUBLZVQX-UHFFFAOYSA-N
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应用
1,4-Naphthoquinone is the key structural moiety of many anticancer and antifungal agents.
It can be used to synthesize:
Additional appilcation include:
It can be used to synthesize:
- 3,3-Disubstituted oxindoles via asymmetric Michael addition to oxindole.
- Bioactive isoindolines via asymmetric 1,3-dipolar cycloaddition to azomethine ylides generated in situ from aldehydes and diethyl aminomalonate.
- α,α-Difluoro-β-hydroxy ketone via ‘on water′ catalyst-free Mukaiyama-aldol reaction with difluoroenoxysilane.
- 2-Hydroxy-3-anilino-1,4-naphthoquinone, which shows potent in vivo antimalarial activity.
Additional appilcation include:
- As an arylation reagent for the α-arylation of aldehydes.
- As a starting material in the multi-step synthesis of benz[f]indole-4,9-diones.
警示用语：
Danger
危险分类
Acute Tox. 1 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1C - Skin Sens. 1 - STOT SE 3
靶器官
Respiratory system
储存分类代码
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
WGK
WGK 3
闪点(°F)
285.8 °F
闪点(°C)
141 °C
个人防护装备
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
1, 4-Naphthoquinone.
Yu J S.
Synlett, 25(16), 2377-2378 (2014)
Design, synthesis and evaluation of novel 1, 4-naphthoquinone derivatives as antifungal and anticancer agents.
Tandon V K, et al.
Bioorganic & Medicinal Chemistry Letters, 14(5), 1079-1083 (2004)
Barbara Krajewska et al.
Bioorganic & medicinal chemistry, 15(12), 4144-4151 (2007-04-10)
In their inhibition-inducing interactions with enzymes, quinones primarily utilize two mechanisms, arylation and oxidation of enzyme thiol groups. In this work, we investigated the interactions of 1,4-naphthoquinone with urease in an effort to estimate the contribution of the two mechanisms
Rita Gatti et al.
Analytical and bioanalytical chemistry, 405(2-3), 817-825 (2012-07-24)
The use of 1,4-naphthoquinone as an advantageous pre-column reagent for liquid chromatography analysis of aliphatic thiol compounds is proposed. The compound reacts selectively in mild conditions (5 min at room temperature; pH 7.5) with thiol function. The resulting adducts were
Jan Bitenc et al.
Materials (Basel, Switzerland), 13(3) (2020-01-25)
Organic cathode materials are promising cathode materials for multivalent batteries. Among organic cathodes, anthraquinone (AQ) has already been applied to various metal‒organic systems. In this work, we compare electrochemical performance and redox potential of AQ with 1,4-naphthoquinone (NQ) and 1,4-benzoquinone
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