22748-16-9

Basic information

• Product Name: 4,4-DIMETHYL-2-CYCLOPENTEN-1-ONE
• Synonyms: 4,4-Dimethyl-2-cyclopenten-1-one 99%;4,4-dimethylcyclopent-2-enone;4,4-DIMETHYL-2-CYCLOPENTEN-1-ONE
• CAS NO: 22748-16-9
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.15
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 22748-16-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 174-175 °C
• Boiling Point: 158 °C(lit.)
• Flash Point: 115 °F
• Appearance: /
• Density: 0.903 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.09mmHg at 25°C
• Refractive Index: n20/D 1.457(lit.)
• CAS DataBase Reference: 4,4-DIMETHYL-2-CYCLOPENTEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-DIMETHYL-2-CYCLOPENTEN-1-ONE(22748-16-9)
• EPA Substance Registry System: 4,4-DIMETHYL-2-CYCLOPENTEN-1-ONE(22748-16-9)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 22748-16-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 115, p. 10056, 1993 DOI: 10.1021/ja00075a022Organic Syntheses, Coll. Vol. 8, p. 208, 1993

General Description

4,4-Dimethyl-2-cyclopenten-1-one is an α,β-unsaturated carbonyl compound and was reported to exhibit the higher tumor-specific cytotoxicity against oral human normal and tumor cells. 4,4-Dimethyl-2-cyclopenten-1-one was identified as one of the constituents in the essential oil of Tagetes minuta L by GC-MS.

InChI:InChI=1/C7H10O/c1-7(2)4-3-6(8)5-7/h3-4H,5H2,1-2H3

Upstream product

• 1195-91-1 2-bromodimedone 
• 61031-76-3 2,2-dimethyl-4-oxopentenal 
• 62535-33-5 1-diazo-5-methyl-hex-4-en-2-one 
• 19184-67-9 methyl 3,3-dimethylglutarate 
• 23151-06-6 2,2-dimethyl-pent-4-ynal 
• 100688-88-8 3-ethoxy-5-methyl-2-cyclopenten-1-one 
• 71221-65-3 5,5-dimethyl-1,6-heptadien-3-ol 
• 71221-68-6 4,4-dimethylbicyclo<3.2.0>heptan-2-ol 
• 17804-59-0 diethyl 3,3-dimethylglutarate 
• 4839-46-7 3,3-Dimethylglutaric acid 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 556-82-1 3-methyl-2-buten-1-ol 
• 1753-37-3 4,4-dimethyl-5-hexen-2-one 
• 2978-30-5 2,2-dimethylpent-4-enenitrile 

Downstream Products

• 145728-47-8 6,6-Dimethyl-1-phenyl-spiro[2.4]hept-4-ene 
• 82253-47-2 4,4-dimethyl-1-triethylsilyloxycyclopentene 
• 105230-73-7 2,2-Dimethyl-4-oxo-6-vinyl-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 103381-68-6 (2R,3S)-2-((S)-1-Hydroxy-2,2-dimethyl-but-3-enyl)-4,4-dimethyl-3-phenylselanyl-cyclopentanone 
• 103381-68-6 (2R,3S)-2-((R)-1-Hydroxy-2,2-dimethyl-but-3-enyl)-4,4-dimethyl-3-phenylselanyl-cyclopentanone 
• 87568-97-6 4-(3-butenyl)-3,3-dimethylcyclopentanone 
• 20500-49-6 3,3-dimethylcyclopentanone 
• 19037-72-0 4,4-dimethyl-cyclopentene 
• 94348-65-9 2-[hydroxy(phenyl)methyl]-4,4-dimethylcyclopent-2-en-1-one 
• 21428-66-0 2-bromo-4,4-dimethylcyclopent-2-en-1-one 
• 244308-21-2 1-(4,4-dimethoxy-1-methylbutyl)-4,4-dimethylcyclopent-2-en-1-ol 
• 1035798-53-8 6a-tert-Butoxycarbonylmethyl-5,5-dimethyl-3-phenylsulfanyl-1,2,4,5,6,6a-hexahydro-pentalene-1-carboxylic acid ethyl ester 
• 1159918-98-5 3,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopentanone 
• 1470061-20-1 C₂₂H₃₂O₂ 

Relevant articles and documents

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Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates

Described is the development of a highly efficient 2πdisrotatory ring-opening aromatization sequence using bicyclo[3.1.0]hexan-2-ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines or alcohols formation of substituted anilines or ethers, respectively, is achieved. Additionally, the utility of this method was demonstrated in a short synthesis of sekikaic acid methyl ester. Cracked open: A highly efficient thermal 2πdisrotatory ring-opening aromatization sequence of bicyclo[3.1.0]hexan-2-ones is described. The transformation proceeds in sulfolane to give uniquely substituted benzoates. In the presence of either amines or alcohols, formation of substituted anilines or ethers, respectively, is achieved.

A simple strategy for spirocyclopentannulation of cyclic ketones. Formal total synthesis of (±)-acorone

A general and simple methodology for spirocyclopentannulation of cyclic ketones (or 4,4-disubstituted cyclopentenones from acyclic ketones) and its application in the synthesis of the spirodienone 7 via a prochiral precursor constituting a formal total synthesis of (±)-acorone (6), are described.