88444-72-8

Usage

InChI:InChI=1/C9H16O/c1-8(7-10)9-5-3-2-4-6-9/h10H,2-7H2,1H3

Upstream product

• 108-94-1 cyclohexanone 
• 121821-93-0 3-methyl-1-oxaspiro<3.5>nonan-2-one 
• 63963-01-9 ethyl 2-cyclohexilidenepropionate 
• 131436-16-3 3-(hydroxymethyl)-3-methyloxetan-2-one-4-spirocyclohexane 

Downstream Products

• 110914-79-9 2-butoxy-4-(1-cyclohexenyl)-4-methyltetrahydrofuran 
• 306326-79-4 4-cyclohexylidene-2-methylpent-1-en-3-ol 
• 264879-08-5 4-cyclohexylidene-2-methylpent-1-en-3-one 
• 264879-09-6 4-cyclohexylidenepent-1-en-3-one 
• 7071-29-6 4-cyclohexylidenepent-1-en-3-ol 
• 7062-12-6 2-(cyclohexylidene)propionaldehyde 
• 3908-31-4 1-Isopropenyl-1-cyclohexanol 

Relevant academic research and scientific papers

Synthesis of All-Carbon Quaternary Centers by Palladium-Catalyzed Olefin Dicarbofunctionalization

The redox-neutral dicarbofunctionalization of tri- and tetrasubstituted olefins to form a variety of (hetero)cyclic compounds under photoinduced palladium catalysis is described. This cascade reaction process was used to couple styrenes or acryl amides with a broad range of highly decorated olefins tethered to aryl or alkyl bromides (>50 examples). This procedure enables one or two contiguous all-carbon quaternary centers to be formed in a single step. The products could be readily diversified and applied in the synthesis of a bioactive oxindole analogue.

Mizoroki–Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers

We report non-decarbonylative Mizoroki–Heck reactions of amide derivatives. The transformation relies on the use of nickel catalysis and proceeds using sterically hindered tri- and tetrasubstituted olefins to give products containing quaternary centers. The resulting polycyclic or spirocyclic products can be obtained in good yields. Moreover, a diastereoselective variant of this method gives access to an adduct bearing vicinal, highly substituted sp3 stereocenters. These results demonstrate that amide derivatives can be used as building blocks for the assembly of complex scaffolds.

Nazarov cyclization of 4-cycloalkylidene-5-(trimethylsilyl)pent-1-en-3-one derivatives. Synthesis of spiro[4.5]decane, Spiro[4.4]nonane, and Their derivatives

Spiro[4.5]decane and spiro[4.4]nonane ring systems were synthesized by FeCl3-induced Nazarov cyclization of α-(trimethylsilylmethyl)divinyl ketone derivatives. It was found that the double bond position of the product is controlled by the presence/absence of α'-substituent, while trimethylsilyl group is essential to obtain the products in good yields. Spiro[4.4]nonanes having exo-methylene group underwent rearrangement to bicyclo[4.3.0]nonanes. (C) 2000 Elsevier Science Ltd.

A Practical and Efficient Method for the Synthesis of β-Lactones

This paper describes a convenient one-step preparation of β-lactames based on the addition of thiol ester enolates to carbonyl compounds.Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce β-lactones in good to excellent yield.The new β-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns.In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded β-lactone diasteromers, and in some cases the reaction proceeds with excellent stereoselectivity.In conjunction with the stereospecific decarboxylation of β-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.