7577-74-4

Basic information

• Product Name: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-6-methyl-
• CAS NO: 7577-74-4
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Mol File: 7577-74-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-6-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-6-methyl-(7577-74-4)
• EPA Substance Registry System: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-6-methyl-(7577-74-4)

Safety Data

• Hazardous Substances Data: 7577-74-4(Hazardous Substances Data)

Upstream product

• 95-48-7 ortho-cresol 
• 64-19-7 acetic acid 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 103855-89-6 2-Methyl-5-morpholino-phenol 
• 24243-06-9 3-methyl-1,5-diphenylpenta-1,4-diyn-3-ol 
• 111562-34-6 2-methyl-5-phenylethynyl-phenol 
• 108852-15-9 1-methyl-2-phenylethynyl-cyclohexa-3,5-diene-1,2-diol 
• 100612-86-0 2-(3-hydroxy-4-methyl-phenyl)-acetoacetic acid ethyl ester 
• 1724-25-0 6-acetoxy-hepta-3t,5ξ-dienoic acid cyclohexylamide 
• 68143-76-0 6-methyl-2-(phenylthio)phenol 
• 100396-73-4 2-methyl-4-(phenylthio)phenol 
• 99595-47-8 5-ethynyl-2-methyl-phenol 
• 108842-62-2 6,6'-dimethyl-3,3'-ethynediyl-di-phenol 
• 59443-97-9 5-diethylamino-2-methyl-phenol 
• 105901-78-8 5-benzenesulfonyl-2-methyl-phenol 
• 99986-36-4 N-(3-hydroxy-4-methyl-phenyl)-glycine ethyl ester 
• 100143-04-2 (4-acetoxy-4-methyl-5-oxo-cyclohex-2-enyl)-malononitrile 

Relevant articles and documents

Competitive Pseudopericyclic [3,3]- and [3,5]-Sigmatropic Rearrangements of Trichloroacetimidates

The Woodward-Hoffmann rules predict whether concerted pericyclic reactions are allowed or forbidden based on the number of electrons involved and whether the cyclic orbital overlap involves suprafacial or antarafacial orbital overlap. Pseudopericyclic reactions constitute a third class of reactions in which orthogonal orbitals make them orbital symmetry allowed, regardless of the number of electrons involved in the reaction. Based on the recent report of eight-centered ester rearrangements, it is predicted that the isoelectronic eight-centered rearrangements of imidates would also be allowed. We now report that these rearrangements occur, and indeed, an eight-centered rearrangement is slightly favored in at least one case over the well-known six-centered Overman rearrangements, in a trichloroacetimidoylcyclohexadienone, a molecular system where both rearrangements are possible.

Oxidation of o-isopropylphenol with lead tetraacetate: Synthesis of the unit of celastroidin terpenes by the Diels-Alder condensation

Lead tetraacetate oxidation of o-isopropyl phenol under various conditions led to the dienone acetate which, when dimerized, represents a central part of the celastroidin penta- and hexa-terpenes (natural products from the Mexican shrub Hippocratea Celastroides). Six oxidation products formed in this reaction (the iso-propyl dienolone acetate, two dimers, benzoquinone, and two phenol acetates) were identified with help of 2D and 3D NMR, GC and LC-MS. From this, we concluded that the dimer skeleton observed for the dienolone acetate in natural products corresponded to the product from the photochemical pathway, and that the synthetic dimer has the opposite geometry; this was verified by molecular modelling. The oxidation of the second compound, o-cresol, leads to a similar profile of products.

PHOTOLACTONIZATION : A NOVEL SYNTHETIC ENTRY TO MACROLIDES

o-Quinol acetates, hydroxyalkyalted at C(6), are easily accesible from simple phenols by Wessely acetoxylation (preferentially catalyzed by BF3).On UV irradiation ( in the presence of an appropriate tertiary amine), they are smoothly converted to macrocyclic lactones.Subtle conditions have been elaborated to lead to high overall yields, and the scope of the conversion of phenols to macrolides has been elucidated.