17299-35-3

Usage

InChI:InChI=1/C10H16O/c1-10(2,3)8-5-4-6-9(11)7-8/h7H,4-6H2,1-3H3

Upstream product

• 71712-68-0 Phosphoric acid diethyl ester 3-oxo-cyclohex-1-enyl ester 
• 594-19-4 tert.-butyl lithium 
• 56671-81-9 3-bromo-2-cyclohexen-1-one 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 126754-28-7 trans-2-chloro-3-(1,1-dimethylethyl)cyclohexanone 
• 80663-82-7 4-tert-butyl-3-chlorocyclohex-2-en-1-ol 
• 144890-13-1 diethyl 7,7-dimethyl-2,6-dioxooctylphosphonate 
• 88841-83-2 3-(Phenylseleno)-2-cyclohexen-1-one 
• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 3419-66-7 1-tert-butyl-1-cyclohexene 
• 930-68-7 cyclohexenone 
• 504-02-9 1,3-cylohexanedione 
• 69035-58-1 1-(tert-butyl)cyclohex-2-en-1-ol 
• 71837-46-2 3-(1,1-dimethylethyl)-1-(trimethylsiloxy)cyclohexene 

Downstream Products

• 64207-29-0 3-tert-butylcyclohex-2-en-1-ol 
• 99942-89-9 Acetic acid 3-tert-butyl-cyclohex-2-enyl ester 
• 72029-73-3 (R)-(+)-3-tert-butylcyclohexanone 
• 57287-85-1 (3S)-3-tert-butylcyclohexanone 
• 96965-13-8 benzenesulfonylhydrazone of 3-tert-butylcyclohex-2-en-1-one 

Relevant academic research and scientific papers

Synthesis of Methylenebicyclo[3.2.1]octanol by a Sm(II)-Induced 1,2-Rearrangement Reaction with Ring Expansion of Methylenebicyclo[4.2.0]octanone

Direct conversion of methylenebicyclo[4.2.0]octanone to methylenebicyclo[3.2.1]octanol by a Sm(II)-induced 1,2-rearrangement with ring expansion of the methylenecyclobutane is described. Three conditions were optimized to allow the adaptation of this approach to various substrates. A rearrangement mechanism is proposed involving the generation of a ketyl radical and cyclopentanation by ketyl-olefin cyclization, followed by radical fragmentation and subsequent protonation.

Palladium-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxygen in aqueous solvent

A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed. (Chemical Equation Presented).

Stereoselective aziridination of cyclic allylic alcohols using chloramine-T

The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC6H4SO 2NClNa, TsNClNa and t-BuSO2NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis-hydroxy aziridine, whilst complete cis- diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis-stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.

Highly efficient methods for the one-pot synthesis of β-substituted enones

A new mild and practically convenient one-pot procedure for the direct β-substitution of enones, developed using a conjugate addition-oxidation strategy with a full range of copper based reagents and N-tert- butylphenylsulfinimidoyl chloride, was analyzed. To start the investigation reaction of a simple Gilman cuprate, lithium di-n-butylcuprate, with cyclohex-2-enone was performed. The desired one-pot transformation was found to be achievable, albeit in a low 39% yield. The application of a series of individual organocuprate reagents was also investigated. It was observed that the technique provided good to excellent yields of β-substituted enones from all of the unsaturated starting materials employed.

One-pot β-substitution of enones with alkyl groups to β-alkyl enones

Vinylic hydrogens at the β-position of enones were effectively substituted with alkyl groups in a one-pot procedure to afford β-alkyl enones in good to high isolated yields by conjugate addition of higher-order dialkyl cyanocuprates to enones, followed by a reaction with N-tert-butylbenzenesulfinimidoyl chloride at -78 °C. The Royal Society of Chemistry 2005.

Lone selectivity of the decatungstate-sensitized photooxidation of 1-substituted cycloalkenes

Decatungstate-sensitized oxidation of alkyl and phenyl substituted cycloalkenes in the presence of molecular oxygen shows a general preference for hydrogen abstraction on the congested side of the double bond.

Carbonyl transposition on organoselenium compounds

Carbonyl conjugated vinylic selenides undergo 1,3 and 1,5-carbonyl transposition sequences through organometallic reagents addition reactions followed by acid hydrolysis.

Iodotrimethylsilane-Promoted Additions of Monoorganocopper Compounds to α,β-Unsaturated Ketones, Esters, and Lactones

Conjugate additions with the efficient monoorganocopper-iodotrimethylsilane combination, exemplified mainly with methylcopper, butylcopper, and tert-butylcopper, proceed cleanly, smoothly, and rapidly to a variety of α,β-unsaturated carbonyl compounds; cy

A New Annulation Reagent, 2-Oxo-3-alkenylphosphonates. Reactions with Carbonyl-Stabilized Carboanions or Silyl Enol Ethers Leading to Cyclohexanones

The reactions of 2-oxo-3-alkenylphosphonates with carbonyl-stabilized carbanions directly lead to 2-cyclohexen-1-ones through a sequence of Michael reaction and intramolecular Horner-Emmons olefination.On the other hand, the Lewis acid-mediated reactions with silyl enol ethers produce 1,5-diketones as Michael adducts, which then undergo cyclization on treatment with sodium hydride or triethylamine/zinc (II) bromide to afford 2-cyclohexen-1-ones or 2-phosphinyl-2-cyclohexen-1-ones, respectively.