535-86-4

Basic information

• Product Name: 3-methyl-5-propan-2-yl-cyclohex-2-en-1-one
• Synonyms: 2-Cyclohexen-1-one, 3-methyl-5- (1-methylethyl)-; 3-Methyl-5-(1-methylethyl)-2-cyclohexen-1-one; 535-86-4; Cyclosal; Hexetone; Homocamfin; Methylisopropylcyclohexenone; m-Menth-6-en-5-one
• CAS NO: 535-86-4
• Molecular Formula: C10H16O
• Molecular Weight: 152.2334
• Mol File: 535-86-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 244°Cat760mmHg
• Flash Point: 90.9°C
• Appearance: /
• Density: 0.915g/cm³
• Vapor Pressure: 0.0311mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: 3-methyl-5-propan-2-yl-cyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-5-propan-2-yl-cyclohex-2-en-1-one(535-86-4)
• EPA Substance Registry System: 3-methyl-5-propan-2-yl-cyclohex-2-en-1-one(535-86-4)

Safety Data

• Hazardous Substances Data: 535-86-4(Hazardous Substances Data)

Usage

General Description

3-methyl-5-propan-2-yl-cyclohex-2-en-1-one, also known as Meldrum's acid, is a chemical compound with a molecular formula of C10H18O. It is a colorless liquid with a fruity odor, and it is commonly used as a building block in the synthesis of various organic compounds. Meldrum's acid has applications in pharmaceuticals, agrochemicals, and materials science, and it is known for its ability to undergo a variety of reactions, including esterification, amidation, and condensation. The compound is considered to be stable under normal conditions, but it should be handled with care due to its potential for irritation to the skin, eyes, and respiratory system. Overall, 3-methyl-5-propan-2-yl-cyclohex-2-en-1-one is a versatile and important chemical that plays a key role in organic synthesis.

InChI:InChI=1/C10H16O/c1-7(2)9-4-8(3)5-10(11)6-9/h5,7,9H,4,6H2,1-3H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 78-84-2 isobutyraldehyde 
• 24079-95-6 2-Methyl-6-(1-methylethyl)-4-oxo-2-cyclohexen-1-carbonsaeure-ethylester 
• 55901-63-8 ethyl isobutylidene-acetylacetate 
• 112632-68-5 4-iso-propyl-2,6-heptanedione 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 30594-34-4 diethyl 4-isopropyl-1,2,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate 

Downstream Products

• 859179-13-8 m-menth-6-en-5-ylamine 
• 91250-83-8 1,3-Dimethyl-5-isopropyl-cyclohexadien-(1,3) 
• 856187-67-2 3-isopropyl-1-methyl-5-oxo-cyclohexanecarbonitrile 
• 64180-63-8 4-((1R,3R)-3-Isopropyl-1-methyl-5-oxo-cyclohexyl)-pent-4-enal 
• 116530-67-7 5-bromo-m-menthane 
• 95709-40-3 m-menth-6-en-5-one semicarbazone 
• 64180-81-0 (3R,5R)-3-(4-Hydroxy-1-methylene-butyl)-5-isopropyl-3-methyl-cyclohexanone 
• 518034-59-8 3-isopropyl-5-methycyclohexanone 
• 10488-20-7 m-menthan-5-ol 

Relevant articles and documents

Reaction of CH-acids with Michael acceptors in the presence of potassium carbonate. Syntheses of 6-acetyl- and 3,5-dialkylcyclohex-2-enones

The reaction of acetylacetone with α,β-enones in the presence of potassium carbonate affords 6-acetylcyclohex-2-enones. The assembly of two acetoacetate and one alkanal molecules gives 3,5-dialkylcyclohex-2-enones. Facile one-pot procedures for these reactions were developed.

Recyclization of 1,4-dihydropyridine derivatives in acidic medium

The recyclization of 1,4-dihydropyridines in aqueous-alcoholic hydrochloric acid medium proceeds with cleavage of a C-N bond and pyridine ring opening. Cyclohexenone derivatives are formed as a result of the subsequent intramolecular crotonic condensation of the acyclic intermediate. The leaving carbonyl substituents depart simultaneously with recyclization, depending on the acidity of the reaction medium.

Regio- and Stereoselectivity of the Lactone Formation via Hydrolysis of the PO-Olefination Products of α,β-Epoxycyclohexanones

PO-Olefination of the diastereomeric pulegone oxides 1 and 2 with 9a leads to (E,Z) esters, 1 affording mainly (E)-3, and 2 predominantly (Z)-4. (Z)-4 hydrolyzes to give a mixture of γ- and δ-lactones 6-8; whereas (Z)-3 yields stereoselectively the δ-lactone 5. - The epoxy ketone 12 reacts with 9b to give the (E,Z) ester 13. (Z)-13 stereoselectively yields the γ-lactone 14.