6296-98-6

Usage

Synonyms

dihydroacenaphthylene-4-ol

Chemical class

Naphthalenes

Physical state

Colorless to light yellow liquid

Odor

Floral, green, and woody

Applications

a. Flavors and fragrances
b. Perfumes and cosmetics
c. Intermediate in chemical and pharmaceutical manufacturing

Hazardous nature

Slightly hazardous

Safety regulations

Strict safety regulations required for use and handling to avoid potential risks

Upstream product

• 111013-13-9 4-methoxy-1,2-dihydroacenaphthylene 
• 23204-36-6 3-hydroxy-1,8-naphthalic acid anhydride 
• 10060-33-0 dimethyl naphthalene-1,8-dicarboxylate 
• 111013-15-1 dimethyl 3-methoxynaphthalene-1,8-dicarboxylate 
• 111013-16-2 1,8-bis(bromomethyl)-3-methoxynaphthalene 
• 111036-23-8 (3-methoxynaphthalene-1,8-diyl)dimethanol 
• 4657-97-0 4-aminoacenaphthene 

Relevant academic research and scientific papers

PYRAZOLE-CONTAINING MACROPHAGE MIGRATION INHIBITORY FACTOR INHIBITORS

In one aspect, the invention comprises compounds that bind and inhibit macrophage migration inhibitory factor. In another aspect, the invention provides methods of treating inflammatory disease, neurological disorders and cancer using the compounds of the invention.

Optimization of Pyrazoles as Phenol Surrogates to Yield Potent Inhibitors of Macrophage Migration Inhibitory Factor

Macrophage migration inhibitory factor (MIF) is a proinflammatory cytokine that is implicated in the regulation of inflammation, cell proliferation, and neurological disorders. MIF is also an enzyme that functions as a keto–enol tautomerase. Most potent MIF tautomerase inhibitors incorporate a phenol, which hydrogen bonds to Asn97 in the active site. Starting from a 113-μm docking hit, we report results of structure-based and computer-aided design that have provided substituted pyrazoles as phenol alternatives with potencies of 60–70 nm. Crystal structures of complexes of MIF with the pyrazoles highlight the contributions of hydrogen bonding with Lys32 and Asn97, and aryl–aryl interactions with Tyr36, Tyr95, and Phe113 to the binding.

Detection of the 1,2-Didehydronaphthalene to 1H-Indenylidenecarbene Rearrangement by Intramolecular Trapping in a Flash Vacuum Pyrolytic Reaction

Flash vacuum pyrolysis of 9-methyl-1,3-dihydronaphthofuran-1,3-dione (8) at 750-880 deg gave exclusively 1H-cyclopentindene (9) and of 8-methyl-1,2-dihydrocyclobutanaphthalene-1.2-dione (10) at 600-840 deg gave a mixture of (9) and acenaphthylene.Acenaphthylen-4-ol (12) was synthesized and found to be stable to flash vacuum pyrolysis over the temperature range 600-900 deg.These findings are discussed in relation to the rearrangement described in the title.