16112-10-0

Basic information

• Product Name: 1-ACETYL-1-CYCLOPENTENE
• Synonyms: 1-ACETYL-1-CYCLOPENTENE;Ethanone, 1-(1-cyclopenten-1-yl)- (9CI);1-acetylcyclopentene;1-(1-Cyclopentenyl)ethanone;1-Acetylcyclopent-1-ene;Methyl (1-cyclopentenyl) ketone;1-(cyclopent-1-en-1-yl)ethanone;1-Acetyl-1-cyclopentene 97%
• CAS NO: 16112-10-0
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.15
• Product Categories: ACETYLGROUP;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 16112-10-0.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 70 °C/20 mmHg(lit.)
• Flash Point: 59 °C
• Appearance: /
• Density: 0.955 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.965mmHg at 25°C
• Refractive Index: n20/D 1.483(lit.)
• CAS DataBase Reference: 1-ACETYL-1-CYCLOPENTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYL-1-CYCLOPENTENE(16112-10-0)
• EPA Substance Registry System: 1-ACETYL-1-CYCLOPENTENE(16112-10-0)

Safety Data

• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 16112-10-0(Hazardous Substances Data)

Usage

Uses

1-Acetyl-1-cyclopentene may be used in the preparation of the following allenylcycloalkanes:1-vinylidenyl-2-[4-(trimethylsilyl)-3-butynyl]-cyclopentane1-vinylidenyl-2-(3-butynyl)-cyclopentane

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 450, 1979 DOI: 10.1021/jo01317a033Tetrahedron Letters, 15, p. 1623, 1974

General Description

1-Acetyl-1-cyclopentene is a cyclic alkene. Its lithium enolate undergoes Brook rearrangement-mediated [3+4] annulation with 3-alkyl-3-haloacryloylsilanes to afford tricyclo[5.3.0.01,4]decenone derivatives. Asymmetric oxidative Heck reaction of 1-acetyl-1-cyclopentene in the presence of a Pd-ligand has been reported.

InChI:InChI=1/C7H10O/c1-6(8)7-4-2-3-5-7/h4H,2-3,5H2,1H3

Upstream product

• 4709-59-5 ethyl 2-(1-cyclohexenyl)acetate 
• 18294-87-6 1-cyclohexenylacetic acid 
• 591-49-1 1-methylcyclohex-1-ene 
• 64-19-7 acetic acid 
• 142-29-0 cyclopentene 
• 933-05-1 cyclopentyl acetate 
• 59231-23-1 7-methylsulfanyl-hept-6-en-2-one 
• 75-89-8 2,2,2-trifluoroethanol 
• 82031-95-6 1,1,2,2,3,3,4,4,4-Nonafluoro-butane-1-sulfonic acid (1R,2S)-2-ethynyl-cyclopentyl ester 
• 83135-33-5 1-Acetyl-cyclopentanecarboxylic acid allyl ester 
• 14579-05-6 cyclopentyltrimethylsilane 
• 75-36-5 acetyl chloride 
• 7446-70-0 aluminium trichloride 
• 75-09-2 dichloromethane 

Downstream Products

• 54125-38-1 (1RS,2RS)-2-acetylcyclopentanecarbonitrile 
• 3197-74-8 1-(1'-hydroxyethan-1'-yl)cyclopentene 
• 172822-91-2 (S)-1-(1-cyclopent-1-enyl)ethanol 
• 172139-04-7 (R)-1-(1-cyclopent-1-enyl)ethanol 
• 403641-43-0 (-)-1-(2-methyl-1-cyclopentyl)-ethanone 
• 1601-00-9 1-(2-methyl-1-cyclopentyl)-ethanone 
• 1226798-82-8 5-methyl-3-phenyl-7,8-dihydro-6Н-cyclopenta[e]pyrazolo[1,5-a]pyrimidine 

Relevant articles and documents

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Substituted cis-hydrindan-4-ones by sequential cycloadditions

The synthesis of substituted cis-hydrindan-4-ones is reported. Particular emphasis was placed on the diastereoselective construction of quaternary stereogenic ring carbon atoms. An intermolecular asymmetric Al(III)-promoted (4+2)-cycloaddition served as the principal C/C-connecting tool. Opportunities for the further structural elaboration of the (4+2)-cycloadducts were explored.

The intramolecular Morita-Baylis-Hillman-type alkylation reaction

From the initial development of a homologous Morita-Baylis-Hillman reaction utilizing epoxides as electrophiles, the method was expanded to enable the exclusively organocatalyzed intramolecular allylation of enones and to develop the intramolecular MBH-type alkylation of activated alkenes. We successfully utilized both enones and unsaturated thioesters as the activated alkene component. This work, carried out using stoichiometric amounts of the trialkylphosphine, gave an array of functionalized five- and six-membered carbocycles in high yields. With the cycloalkylation of enones and thioesters, conditions that allowed the use of substoichometric amounts of the phosphine catalyst were developed. As a result both five- and six-membered rings can be formed efficiently with little to no loss in yield upon comparison to yields obtained when stoichiometric amounts of trialkylphosphines were employed. We isolated, for the first time, an MBH-type intermediate exhibiting unprecedented trans geometry of the phosphonium salt and acyl group.