74567-38-7

Basic information

• Product Name: 4-METHYL-4-P-TOLYLCYCLOPENT-2-ENONE
• Synonyms: 4-METHYL-4-P-TOLYLCYCLOPENT-2-ENONE
• CAS NO: 74567-38-7
• Molecular Formula: C₁₃H₁₄O
• Molecular Weight: 186.25
• Mol File: 74567-38-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-METHYL-4-P-TOLYLCYCLOPENT-2-ENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-4-P-TOLYLCYCLOPENT-2-ENONE(74567-38-7)
• EPA Substance Registry System: 4-METHYL-4-P-TOLYLCYCLOPENT-2-ENONE(74567-38-7)

Safety Data

• Hazardous Substances Data: 74567-38-7(Hazardous Substances Data)

Upstream product

• 122-00-9 para-methylacetophenone 
• 143768-84-7 (3aRS,4RS,7SR,7aSR)-3-(p-tolyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one 
• 766-97-2 4-n-methylphenylacetylene 
• 1203581-26-3 C₁₆H₂₂OSi 
• 74567-37-6 2-methyl-2-(p-tolyl)-4-chloro-4-pentenal 
• 176659-75-9 N-Allyl-2-p-tolyl-propionamide 
• 176659-76-0 2-Methyl-2-p-tolyl-pent-4-enenitrile 
• 938-94-3 (R,S)-2-(4'-methylphenyl) propionic acid 
• 433732-53-7 5-methyl-5-p-tolyl-hepta-1,6-dien-3-ol 
• 94853-56-2 3-methyl-3-(4-methylphenyl)-pent-4-enal 
• 188476-09-7 1-((E)-2-Allyloxy-1-methyl-vinyl)-4-methyl-benzene 
• 62083-22-1 2-methyl-2-(4-methylphenyl)-pent-4-en-1-al 
• 927833-56-5 4-methyl-4-(4-methylphenyl)-hepta-1,6-diene 
• 927833-58-7 1-methyl-4-(1-methylcyclopent-3-enyl)benzene 

Downstream Products

• 176659-78-2 4-(p-tolyl)-4,5,5,-trimethyl-2-cyclopentenone 

Relevant articles and documents

Synthesis and application of β-substituted Pauson-Khand adducts: Trifluoromethyl as a removable steering group

Against the rules: The synthesis of the previously unknown β-substituted regioisomers of the intermolecular Pauson-Khand reaction of terminal alkynes is reported. This regiochemistry was achieved by using the trifluoromethyl group as a removable directing group on the alkyne. Copyright

Gold(I)-catalyzed synthesis of highly substituted 2-cyclopentenones from 5-siloxypent-3-en-1-ynes

A highly efficient gold (I)-catalyzed approach towards densely functionalized cyclopentenones possessing a quaternary carbon center, was reported. Methylene chloride was added to a mixture of gold complex [Au{P(C6F5)3}Cl]

A facile total synthesis of (±)-α-cuparenone employing diallylation and RCM as key steps

A short and concise total synthesis of α-cuparenone employing one-pot diallylation and RCM as the key steps is described.

An efficient and practical total synthesis of (±)-α-cuparenone

A one-pot cyclopentannulation approach as the key step for the total synthesis of (±)-α-cuparenone is described. Georg Thieme Verlag Stuttgart.

An expedient protocol for cyclopentenone annulation

A convenient and general protocol for the cyclopentenone annulation process is described.

A ring closing metathesis-based approach to (±)-herbertene, (±)-α-herbertenol, (±)-β-herbertenol and (±)-herbertenediol

An efficient methodology for the synthesis of the aromatic sesquiterpenes (±)-herbertene, (±)-α-herbertenol, (±)-β-herbertenol (±)-herbertenediol and (±)-α-cuparenone, employing a combination of Claisen rearrangement and ring closing metathesis reactions,

An efficient synthesis of α-Cuparenone

Synthesis of α-Cuparenone is described. The key step involved are photorearrangement of α-halo arylketone (4) to 1-methyl-1-(p-tolyl)acetic acid (5) and extremely mild, essentially neutral, room temperature/3-aza-claisen reaction of N-allylamide (6).

Geminal Acylation-Alkylation at a Carbonyl Carbon via Regiospecifically Generated Metalloenamines

A useful procedure for effecting geminal disubstitution at the carbonyl carbon atom of aldehydes and ketones has been developed in which the sequence of reactions results in the replacement of the two carbon-oxygen bonds of the carbonyl function with an acyl group and an alkyl or hydroxyalkyl group.Of particular importance is the facile application of these procedures to the efficient construction of quaternary carbon atoms that bear alkyl appendages containing differentiated functionality.This novel methodology features the initial conversion of carbonyl compounds 1 into the substituted 2-azadienes 10 or 11 by Wittig-Horner reaction.Subsequent reaction of these 2-azadienes produced in situ with n-butyllithium results in the formation of the metalloenamines 12 and 13 (R4 = n-Bu) which undergo reactions with a wide variety of electrophiles to give, after hydrolysis of the intermediate imines, the α-substituted aldehydes 14 or the α-substituted ketones 15 in good of excellent overall yields.New procedures for the annelation of cyclopentenones such as 22 and cyclohexenones 26 at the carbonyl carbon of ketones are described as is an important variant of a directed aldol reaction, 1 --> 28.Although a number of individual manipulations are necessary to effect the geminal disubstitution of a carbonyl functional group, it is generally feasible to execute the entire sequence of reactions in single flask, thereby rendering this methodology very convenient to implement in practice.