17299-35-3

Basic information

• Product Name: 3-tert-butylcyclohex-2-en-1-one
• Synonyms: 3-tert-butylcyclohex-2-en-1-one
• CAS NO: 17299-35-3
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• Mol File: 17299-35-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 224.6°Cat760mmHg
• Flash Point: 91°C
• Appearance: /
• Density: 0.948g/cm³
• Vapor Pressure: 0.0905mmHg at 25°C
• Refractive Index: 1.48
• CAS DataBase Reference: 3-tert-butylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-tert-butylcyclohex-2-en-1-one(17299-35-3)
• EPA Substance Registry System: 3-tert-butylcyclohex-2-en-1-one(17299-35-3)

Safety Data

• Hazardous Substances Data: 17299-35-3(Hazardous Substances Data)

Usage

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

Upstream product

• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 594-19-4 tert.-butyl lithium 
• 80663-82-7 4-tert-butyl-3-chlorocyclohex-2-en-1-ol 
• 88841-83-2 3-(Phenylseleno)-2-cyclohexen-1-one 
• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 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 
• 35376-40-0 trans 4-tert-butylcyclohexen-1-ol 
• 937-07-5 4-tert-butylcyclohex-2-enone 
• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 
• 3419-66-7 1-tert-butyl-1-cyclohexene 
• 144890-13-1 diethyl 7,7-dimethyl-2,6-dioxooctylphosphonate 

Downstream Products

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

Relevant articles and documents

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.

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.

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.