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

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. Used in the Chemical Industry:
1-Acetyl-1-cyclopentene is used as a key intermediate for the synthesis of various complex organic molecules, such as allenylcycloalkanes. Its unique reactivity and ability to undergo specific chemical reactions make it a valuable compound in the synthesis of advanced materials and pharmaceuticals.
2. Used in the Preparation of Allenylcycloalkanes:
1-Acetyl-1-cyclopentene is used as a starting material for the preparation of the following allenylcycloalkanes:
a) 1-Vinylidenyl-2-[4-(trimethylsilyl)-3-butynyl]-cyclopentane
b) 1-Vinylidenyl-2-(3-butynyl)-cyclopentane
These allenylcycloalkanes have potential applications in various fields, including pharmaceuticals, materials science, and chemical research.
3. Used in Research and Development:
1-Acetyl-1-cyclopentene is utilized in research and development for exploring new synthetic routes and reaction mechanisms, particularly in the context of asymmetric oxidative Heck reactions and Brook rearrangement-mediated annulation reactions. Its unique chemical properties make it an interesting compound for scientists to study and develop new methodologies and applications.

Synthesis Reference(s)

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

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

Upstream product

• 708-69-0 cyclohex-1-enyl-malonic acid 
• 108-94-1 cyclohexanone 
• 59253-90-6 cyclopent-1-enecarbonyl chloride 
• 17356-19-3 1-ethynylcyclopentanol 
• 1610-13-5 ethynylcyclopentene 
• 591-49-1 1-methylcyclohex-1-ene 
• 18294-87-6 1-cyclohexenylacetic acid 
• 4709-59-5 ethyl 2-(1-cyclohexenyl)acetate 
• 64-18-6 formic acid 
• 73185-48-5 cyclohex-1-enyl-malonic acid diethyl ester 
• 67-66-3 chloroform 
• 3197-74-8 1-(1'-hydroxyethan-1'-yl)cyclopentene 
• 6140-65-4 1-cyclopentene-1-carboxaldehyde 
• 931-17-9 1,2-Cyclohexanediol 

Relevant articles and documents

Total synthesis and stereochemical revision of the chlorinated sesquiterpene (±)-gomerone C

Red algae from the genus Laurencia (Ceramiales) are the source of over 500 halogenated terpenes, cyclic ethers, and acetogenides, which in some cases have been suggested to serve as chemical defence agents because of their activity against pathogenic marine bacteria and herbivores. In 2008 a Spanish research group reported the isolation and structural elucidation of three novel chlorinated sesquiterpenes, gomerones A-C, from samples of Laurencia majuscula collected at the southern coast of La Gomera, Canary Islands (Scheme 1). The structurally interesting and unprecedented gomerane skeleton in combination with their unexplored biological activity as well as the halogenated nature of these natural products rendered them noteworthy targets for synthesis. Herein, we report a total synthesis of gomerone C (1), which not only represents the first synthesis of a member of this novel class of chlorinated sesquiterpenes, but also resulted in the revision of the relative stereochemistry of gomerone C (1) and hence to a stereochemical reassignment of gomerone B (2).

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.

Palladium-catalyzed asymmetric alkylation in the synthesis of cyclopentanoid and cycloheptanoid core structures bearing all-carbon quaternary stereocenters

General catalytic asymmetric routes toward cyclopentanoid and cycloheptanoid core structures embedded in numerous natural products have been developed. The central stereoselective transformation in our divergent strategies is the enantioselective decarboxylative alkylation of seven-membered β-ketoesters to form α-quaternary vinylogous esters. Recognition of the unusual reactivity of β-hydroxyketones resulting from the addition of hydride or organometallic reagents enabled divergent access to γ-quaternary acylcyclopentenes through a ring contraction pathway or γ-quaternary cycloheptenones through a carbonyl transposition pathway. Synthetic applications of these compounds were explored through the preparation of mono-, bi-, and tricyclic derivatives that can serve as valuable intermediates for the total synthesis of complex natural products. This work complements our previous work with cyclohexanoid systems.

Isomerization of propargylic alcohols into α,β-unsaturated carbonyl compounds catalyzed by the sixteen-electron allyl-ruthenium(II) complex [Ru(η3-2-C3H4Me)(CO)(dppf)] [SbF 6]

The 16-e- (η3-allyl)-ruthenium(II) complex [Ru(η3-2-C3H4Me)(CO)(dppf)][SbF 6] is an efficient catalyst for the regioselective isomerization of terminal propargylic alcohols HC≡CCR1R2(OH) into α,β-unsaturated aldehydes R1R2C=CHCHO or ketones R3R4C=C(R1)COMe (if R2 = CHR3R4) under mild conditions. This complex has been also used as catalyst for the preparation of conjugated 1,3-enynes via dehydration of propargylic alcohols.

Organocatalysis of the Morita-Baylis-Hillman alkylation using trialkylphosphines

Using a catalytic amount of trialkylphosphines, alkyl halides undergo efficient intramolecular Morita-Baylis-Hillman cyclization. Georg Thieme Verlag Stuttgart.

Unprecedented reactivity in the Morita-Baylis-Hillman reaction; intramolecular α-alkylation of enones using saturated alkyl halides

sp3 Hybridized electrophiles, never before used in the organo-mediated Morita-Baylis-Hillman reaction, now facilitate the formation of five- and six-membered enone cycloalkylation products. The Royal Society of Chemistry 2005.

Application of Rh(l)-Catalyzed C - H Bond Activation to the Ring Opening of 2-Cycloalkenones in the Presence of Amines

(matrix presented) Herein described is the application of the Rh(l)-catalyzed C-H bond activation to the ring-opening of 2-cycloalkenones in the presence of cyclohexylamine. This reaction includes the C-C double bond cleavage of 2-cycloalkenones through the conjugate addition of cyclohexylamine followed by the retro-Mannich-type fragmentation. The resulting ring-opened intermediates subsequently underwent either chelation-assisted hydroacylation to afford a ring-opened dicarbonyl compound or β-alkylation via a ring contraction.

Facile approach to versatile chiral intermediates for fused cyclopentanoid natural products

A facile approach to cis- and trans-2-(1-hydroxymethyl)vinyl-1-vinylcyclohexan-1-ols and to the corresponding cyclopentane, cycloheptane, and cyclooctane derivatives has been developed, starting from cycloalkanones involving the key steps of Rupe and Claisen orthoester rearrangements. The formation of intervening products could be explained by allylic strain and π-stacking, respectively.

Siloxyalkyne - Alkene metathesis: Rapid access to highly functionalized enones

Mechanistically intriguing participation of siloxyalkynes occurs in the intramolecular Ru-catalyzed metathesis with terminal alkenes (see scheme; Ms = methanesulfonyl). Combined with efficient protodesilylation, this process resulted in the development of a new method for the synthesis of highly functionalized enones starting from readily accessible acyclic precursors. Heterocyclic and polycyclic compounds were prepared efficiently, which illustrates the generality of this novel method.