Merck
CN
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文件

70372

Sigma-Aldrich

1,4-萘醌

purum, ≥96.5% (HPLC)

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别名:
α-萘醌
经验公式（希尔记法）:
C10H6O2
CAS号:
130-15-4
分子量:
158.15
Beilstein:
878524
EC 号:
204-977-6
MDL编号:
MFCD00001676
PubChem化学物质编号:
329762061
NACRES:
NA.22

等级

purum

质量水平

200

检测方案

≥96.5% (HPLC)

形式

powder

mp

119-122 °C (lit.)
120-124 °C

SMILES string

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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相关类别

应用

1,4-Naphthoquinone is the key structural moiety of many anticancer and antifungal agents.
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

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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)
1, 4-Naphthoquinone.
Yu J S.
Synlett, 25(16), 2377-2378 (2014)
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
Michael G Berg et al.
Molecular and cellular biology, 32(7), 1271-1283 (2012-01-19)
Despite intensive research, there are very few reagents with which to modulate and dissect the mRNA splicing pathway. Here, we describe a novel approach to identify such tools, based on detection of the exon junction complex (EJC), a unique molecular
Don Antoine Lanfranchi et al.
Organic & biomolecular chemistry, 10(31), 6375-6387 (2012-07-11)
Improving the solubility of polysubstituted 1,4-naphthoquinone derivatives was achieved by introducing nitrogen in two different positions of the naphthoquinone core, at C-5 and at C-8 of menadione through a two-step, straightforward synthesis based on the regioselective hetero-Diels-Alder reaction. The antimalarial
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