7214-50-8

Basic information

• Product Name: 5-methylcyclohex-2-en-1-one
• Synonyms: 2-cyclohexen-1-one, 5-methyl-; 5-Methylcyclohex-2-en-1-one
• CAS NO: 7214-50-8
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.1537
• Mol File: 7214-50-8.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 183°C at 760 mmHg
• Flash Point: 61.8°C
• Density: 0.947g/cm³
• Vapor Pressure: 0.788mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: 5-methylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methylcyclohex-2-en-1-one(7214-50-8)
• EPA Substance Registry System: 5-methylcyclohex-2-en-1-one(7214-50-8)

Safety Data

• Hazardous Substances Data: 7214-50-8(Hazardous Substances Data)

Usage

Description

5-Methylcyclohex-2-en-1-one is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and chemicals. It is characterized by its unique cyclic structure and functional groups, which contribute to its reactivity and utility in chemical reactions.

Uses

Used in Pharmaceutical Industry:
5-Methylcyclohex-2-en-1-one is used as a chemical intermediate for the synthesis of 4-1-Hydroxy-2-[3-(4-hydroxyphenyl)-5-methylcyclohexylamino]ethylphenol Hydrochloride (H825390), which is an impurity of Ractopamine (R071400). This application is significant as it aids in the production of pharmaceuticals that can be used for various medical purposes, including the treatment of certain conditions in animals.

Upstream product

• 108-47-4 2,4-lutidine 
• 39511-99-4 2-Hydroxy-5-methyl-1-cyclohexanon 
• 144-62-7 oxalic acid 
• 42747-34-2 3-chloro-5-methylcyclohex-2-enone 
• 591-47-9 4-methylcyclohexene 
• 591-24-2 3-Methylcyclohexanone 
• 91-22-5 quinoline 
• 89616-30-8 2-chloro-5-methyl-cyclohexanone 
• 125787-54-4 3-bromo-5-methylcyclohex-2-enone 
• 61621-44-1 3-Methoxy-5-methylcyclohex-2-en-1-one 
• 141-97-9 ethyl acetoacetate 
• 123-73-9 crotonaldehyde 
• 110317-77-6 ethyl 4-methyl-6-oxocyclohex-1-ene-1-carboxylate 
• 70150-66-2 5-methyl-3-hydroxycyclohex-2-enone 

Downstream Products

• 55373-57-4 trans-3,5-Dimethyl-1-((trimethylsilyl)oxy)-1-cyclohexene 
• 55373-57-4 cis-<(3,5-dimethyl-1-cyclohexen-1-yl)oxy>trimethylsilane 
• 109314-83-2 ((1S,3R)-3-Methyl-5-oxo-cyclohexyl)-dithioacetic acid methyl ester 
• 109314-83-2 ((1S,3S)-3-Methyl-5-oxo-cyclohexyl)-dithioacetic acid methyl ester 
• 77086-41-0 methyl 2-(5-methyl-3-trimethylsiloxycyclohex-2-enyl)propionate 
• 23978-62-3 cis-3-isopropyl-5-methylcyclohexanone 
• 23978-62-3 trans-3-isopropyl-5-methylcyclohexanone 
• 76915-10-1 cis-3-butyl-5-methylcyclohexanone 
• 76915-10-1 trans-5-methyl-3-butylcyclohexanone 
• 125413-74-3 cis-3-tert-butyl-5-methylcyclohexanone 
• 125413-75-4 trans-3-tert-butyl-5-methylcyclohexanone 
• 59962-36-6 (3S,5S)-3-Ethyl-5-methyl-cyclohexanone 
• 67662-98-0 3-methyl-5-propylcyclohexanone 
• 84877-78-1 (3RS,5SR)-5-methyl-3-propylcyclohexanone 

Relevant articles and documents

CeO2-Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones

Direct selective desaturation of carbonyl compounds to synthesize α,β-unsaturated carbonyl compounds represents an environmentally benign alternative to classical stepwise procedures. In this study, we designed an ideal CeO2-supported Pd(II)-on-Au nanoparticle catalyst (Pd/Au/CeO2) and successfully achieved heterogeneously catalyzed selective desaturation of cyclohexanones to cyclohexenones using O2 in air as the oxidant. Besides cyclohexenones, various bioactive enones can also be synthesized from the corresponding saturated ketones under open air conditions in the presence of Pd/Au/CeO2. Preliminary mechanistic studies revealed that α-C-H bond cleavage in the substrates is the turnover-limiting step of this desaturation reaction.

Catalytic Enantioselective Nitroso Diels-Alder Reaction

The nitroso Diels-Alder (NDA) reaction is an attractive strategy for the synthesis of 3,6-dihydro-1,2-oxazines and 1-amino-4-hydroxy-2-ene derivatives. Herein we report the Cu(I)-DTBM-Segphos catalyzed asymmetric intermolecular NDA reaction of variously substituted cyclic 1,3-dienes using highly reactive nitroso compounds derived from pyrimidine and pyridazine derivatives. In most of the cases studied, the cycloadducts were obtained in high yields (up to 99%) with very high regio-, diastereo-, and enantioselectivities (up to regioselectivity > 99:1, d.r. > 99:1, and >99% ee). As an application of this methodology, formal syntheses of conduramine A-1 and narciclasine were accomplished.