88692-77-7

Basic information

• Product Name: Cyclohexanone, 2-[(3,4-dimethoxyphenyl)methylene]-
• Synonyms: 2-(3',4'-dimethoxyphenylmethylene)cyclohexan-1-one;2-Veratryliden-cyclohexanon;2-veratrylidene-cyclohexanone;Cyclohexanone,2-[(3,4-dimethoxyphenyl)methylene];2-(3,4-dimethoxyphenylmethylene)cyclohexanone
• CAS NO: 88692-77-7
• Molecular Formula: C15H18O3
• Molecular Weight: 246.306
• Mol File: 88692-77-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 2-[(3,4-dimethoxyphenyl)methylene]-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2-[(3,4-dimethoxyphenyl)methylene]-(88692-77-7)
• EPA Substance Registry System: Cyclohexanone, 2-[(3,4-dimethoxyphenyl)methylene]-(88692-77-7)

Safety Data

• Hazardous Substances Data: 88692-77-7(Hazardous Substances Data)

Upstream product

• 370873-37-3 2-[(4,5-dimethoxyphenyl)(2-naphthylamino)methyl]cyclohexanone 
• 108-94-1 cyclohexanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 670-80-4 4-cyclohexen-1-ylmorpholine 

Downstream Products

• 18977-33-8 2,6-bis(3,4-dimethoxybenzylidene)-cyclohexan-1-one 

Relevant articles and documents

Redox-Neutral Cobalt(III)-Catalyzed C-H Activation/Annulation of α,β-Unsaturated Oxime Ether with Alkyne: One-Step Access to Multisubstituted Pyridine

A redox neutral Co(III)-catalyzed annulation of α,β-unsaturated oxime ether with alkyne has been reported. Multisubstituted pyridines were synthesized in good yields without the use of any heavy metal oxidants. The developed methodology tolerates a variety of functional groups. Notably, this transformation has been applied to the late-stage modification of the bioactive molecule dehydropregnenolone.

Discovery of new MD2-targeted anti-inflammatory compounds for the treatment of sepsis and acute lung injury

Myeloid differentiation 2 (MD2) is essential to the recognition of lipopolysaccharide (LPS) and the subsequent mediation of toll-like receptor 4 (TLR4)-dependent acute inflammatory disorders including sepsis and acute lung injury. Inhibitors targeting MD2 may provide an alternative means to subdue acute inflammatory diseases. In the present study, 39 bisaryl-1,4-dien-3-one compounds with 5-carbon connection chains were designed and synthesized as MD2 inhibitors based on the analysis of the molecular docking of xanthohumol to MD2. The compound-MD2 interactions were measured by cell-free assays including bis-ANS displacement and SPR, and the active compounds were further tested for MD2 inhibition and anti-inflammatory activities in LPS-challenged macrophages. The most active compound, 1f, was shown to have remarkable protective effects against sepsis shock and pulmonary inflammation. Collectively, we present evidence that bisaryl-1,4-dien-3-one is a new lead structure for the development of anti-inflammatory agents targeting MD2.

Synthesis of 5-aryl-1,2,3,4-tetrahydrobenzo[a]phenanthridines

Previously unknown derivatives of tetrahydro[a]phenanthridine containing annelated benzoquinoline and cyclohexene nuclei were prepared by condensation of azomethines of the 2-naphthylamine series with cyclohexanone. The possibility of synthesis of such compounds without preliminarily preparing Schiff bases was demonstrated. The effect of substituents in the aromatic ring of the azomethine on the yield of the target products was elucidated. The IR, UV, 1H NMR, and mass spectra of the synthesized compounds were discussed.