53666-76-5

Basic information

• Product Name: 4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one
• Synonyms: 4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one
• CAS NO: 53666-76-5
• Molecular Formula: C₁₀H₈O₄
• Molecular Weight: 192.17
• Mol File: 53666-76-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 155 °C(Solv: ethanol (64-17-5))
• Boiling Point: 403.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.412±0.06 g/cm3(Predicted)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one(53666-76-5)
• EPA Substance Registry System: 4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one(53666-76-5)

Safety Data

• Hazardous Substances Data: 53666-76-5(Hazardous Substances Data)

Usage

Synthesis

4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one is obtaned by 2-Hydroxy-5-methoxy-acetophenone with sodium hydride in diethyl carbonate.2-Hydroxy-5-methoxy-acetophenone (1.50 g, 9.03 mmol) in diethyl carbonate (8.3 ml) was added dropwise into a suspension of sodium hydride (60% dispersion in mineral oil, 1.81 g, 45.2 mmol) in diethyl carbonate (8.3 ml) and heated under reflux at 100 ?C for 3 hours. The resultant mixture was left to cool to 0 ?C in an ice bath and quenched by dropwise addition of water until effervescence ceased. The aqueous layer was washed with diethyl ether (3 × 16 ml) then acidified using concentrated hydrochloric acid to pH 1. The precipitate was filtered and washed with water, followed by petroleum ether and left to dry overnight at 90 ?C to give the title compound as a colourless solid (902 mg, 52%): mp: 150 – 153 ?C (Lit.: 155 ?C); vmax/cm-1 3207bw (O-H), 1727s (C=O), 1655m (C=C), 1606s (aro. ring C=C); δH (300 MHz; DMSO-d6) 11.34 (1H, br. s., OH), 7.57 (1H, t, J 8.4, C(7)H), 6.95 (2H, d, J 8.4, C(6)H and C(8)H), 5.51 (1H, s, C(3)H), 3.90 (1H, s, OCH3); δC (75 MHz; DMSO-d6) 167.2 (Ar-C), 161.4 (Ar-C), 157.3 (Ar-C), 155.2 (Ar-C), 133.0 (Ar-CH), 109.2 (Ar-CH), 106.8 (Ar-CH), 105.0 (Ar-C), 90.8 (C(3)H), 56.5 (OCH3); m/z (-ES) 191 (100%, [M-H]-).

Upstream product

• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 105-58-8 Diethyl carbonate 
• 85630-17-7 3-methoxyphenyl N,N-diethylcarbamate 
• 211449-28-4 Diethyl-carbamic acid 2-acetyl-3-methoxy-phenyl ester 

Downstream Products

• 1609132-85-5 C₃₈H₂₆O₄ 
• 1560773-72-9 (S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-5-methoxycoumarin hydrochloride 
• 1560773-61-6 (S)-4-{3-[3-benzyloxy-2-(tert-butoxycarbonylamino)propanoylamino]-4-methoxyphenyl}-5-methoxycoumarin 
• 1560773-49-0 4-(3-amino-4-methoxyphenyl)-5-methoxycoumarin 
• 1560773-38-7 4-(3-amino-4-methoxyphenyl)-5-methoxycoumarin hydrochloride 
• 1560773-27-4 4-(3-tert-butoxycarbonylamino-4-methoxyphenyl)-5-methoxycoumarin 
• 36914-76-8 5-Methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 142732-56-7 4-hydroxy-5-methoxy-3-(3-methoxyphenyl)-1-benzopyran-2-one 
• 124010-44-2 4-hydroxy-5-methoxy-3-(2,4,6-trimethoxyphenyl)-1-benzopyran-2-one 
• 124010-48-6 3-(2,4-dimethoxyphenyl)-4-hydroxy-5-methoxy-1-benzopyran-2-one 
• 124010-45-3 3-(3,4-dimethoxyphenyl)-4-hydroxy-5-methoxy-1-benzopyran-2-one 
• 142732-55-6 4-hydroxy-5-methoxy-3-(2-methoxyphenyl)-1-benzopyran-2-one 
• 124029-22-7 4-hydroxy-5-methoxy-3-(4-methoxyphenyl)-1-benzopyran-2-one 
• 142732-57-8 4-hydroxy-5-methoxy-3-(p-tolyl)-1-benzopyran-2-one 

Relevant articles and documents

TRICYCLIC COMPOUNDS ACTING ON CRBN PROTEINS

The present invention discloses a series of tricyclic compounds and use thereof in preparing a medicament for treating a disease related to CRBN protein. Specifically, the present invention discloses a derivative compound of formula (1) or a pharmaceutically acceptable salt thereof.

Mechanistic studies on the palladium-catalyzed cross-dehydrogenative coupling of 4-phenoxy-2-coumarins: Experimental and computational insights

Delineating the mechanistic features of C-H activation in aryl-heteroaryl coupling is an important step in the design of selective, catalytic processes. Herein we use the intramolecular dehydrogenative coupling of 4-phenoxy-2-coumarins as a model study. Computational results and experimental studies suggest that CMD is operative in the cleavage of both C-H bonds, and that the heteroaryl C-H is cleaved initially.

Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: Quinone oxidoreductase-1 (NQO1)

The synthesis is reported here of two novel series of inhibitors of human NAD(P)H quinone oxidoreductase-1 (NQO1), an enzyme overexpressed in several types of tumor cell. The first series comprises substituted symmetric dicoumarol analogues; the second series contains hybrid compounds where one 4-hydroxycoumarin systemis replaced by a different aromatic moiety. Several compounds show equivalent or improved NQO1 inhibition over dicoumarol, both in the presence and in the absence of added protein. Further, correlation is demonstrated between the ability of these agents to inhibit NQO1 and computed binding affinity. We have solved the crystal structure of NQO1 complexed to a hybrid compound and find good agreement with the in silico model. For both MIA PaCa-2 pancreatic tumor cells and HCT116 colon cancer cells, dicoumarol shows the greatest toxicity of all compounds. Thus, we provide a computational, synthetic, and biological platform to generate competitive NQO1 inhibitors with superior pharmacological properties to dicoumarol. This will allow a more definitive study of NQO1 activity in cells, in particular, its drug activating/detoxifying properties and ability to modulate oncoprotein stability. 2009 American Chemical Society.