(R)-4-Oxocyclopent-2-en-1-yl acetate

Base Information

• Chemical Name: (R)-4-Oxocyclopent-2-en-1-yl acetate
• CAS No.: 59995-48-1
• Molecular Formula: C7H8O3
• Molecular Weight: 140.139
• European Community (EC) Number: 689-037-7
• DSSTox Substance ID: DTXSID30432158
• Nikkaji Number: J403.408B
• Wikidata: Q76414682
• Mol file: 59995-48-1.mol

Synonyms:59995-48-1;(R)-4-Oxocyclopent-2-en-1-yl acetate;(1r)-4-oxocyclopent-2-en-1-yl acetate;(1R)-4-OXO-2-CYCLOPENTEN-1-YL ACETATE;[(1R)-4-oxocyclopent-2-en-1-yl] acetate;(R)-4-acetoxycyclopent-2-enone;2-Cyclopenten-1-one, 4-(acetyloxy)-, (4R)-;SCHEMBL2816076;DTXSID30432158;YNCKAQVPQJWLJW-ZETCQYMHSA-N;4(r)-acetoxycyclopent-2-en-1-one;AMY35665;(r)-4-acetoxy-2-cyclopenten-1-one;MFCD01318189;(R)-4-Oxocyclopent-2-en-1-ylacetate;4alpha-(Acetoxy)-2-cyclopentene-1-one;AS-52468;CS-0053635;P15221;A869072;(1r)(c)\4(c)\oxocyclopent(c)\2(c)\en(c)\1(c)\yl acetate

Chemical Property of (R)-4-Oxocyclopent-2-en-1-yl acetate

Chemical Property:

• Melting Point: 15 °C
• Boiling Point: 45 °C(Press: 0.05 Torr)
• PSA: 43.37000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 0.44710
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 140.047344113
• Heavy Atom Count: 10
• Complexity: 193

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R)-4-Oxocyclopent-2-en-1-ylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1CC(=O)C=C1
• Isomeric SMILES: CC(=O)O[C@@H]1CC(=O)C=C1
• Use Description: (1R)-4-oxocyclopent-2-en-1-yl acetate is a chemical compound with applications in various fields. In the fragrance and flavor industry, it serves as a valuable ingredient for the synthesis of aroma compounds and flavoring agents. Its role is pivotal in enhancing the scent and taste profiles of perfumes, colognes, and food products. Additionally, in academic research and organic chemistry, this compound can be utilized as a building block for the creation of complex organic molecules, facilitating studies in chemical synthesis and chemical biology. Its diverse applications underscore its significance in improving sensory experiences in the fragrance and food industries and advancing chemical research across these diverse fields.

Technology Process of (R)-4-Oxocyclopent-2-en-1-yl acetate

There total 33 articles about (R)-4-Oxocyclopent-2-en-1-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → (R)-4-acetoxycyclopent-2-en-1-one (59995-48-1)

Guidance literature:

With dipyridinium dichromate;

DOI:10.1055/s-2004-834822

Reference yield: 92.0%

(1R,4R)-(+)-4-Hydroxy-2-cyclopentenyl acetate (60410-17-5) → (R)-4-acetoxycyclopent-2-en-1-one (59995-48-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jo402539p

Reference yield: 91.0%

3(S)-acetoxy-5-(R)-hydroxy-cyclopent-1-ene (60895-01-4,61348-01-4) → (R)-4-acetoxycyclopent-2-en-1-one (59995-48-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 5.66667h;

DOI:10.1002/anie.201410419

upstream raw materials:

(R)-(+)-4-hydroxy-2-cyclopentenone

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

(S)-4-tetrahydropyranyloxy-2-cyclopenten-1-one

(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one

Downstream raw materials:

(S)-4-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopent-2-enone

tricyclo[5.2.1.02,6]deca-4,8-dien-3-one

Acetic acid (1R,3aR,4S,7R,7aS)-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-4,7-methano-inden-1-yl ester

(1R,2R,5S)-4-oxobicyclo[3.2.0]hept-2-yl acetate

Refernces

• 1、 Ruider, Stefan A.,Sandmeier, Tobias,Carreira, Erick M.. "Total synthesis of (±)-hippolachnin A". . p. 2378 - 2382. Retrieved 2015.
• 2、 Trost, Barry M.,Masters, James T.,Lumb, Jean-Philip,Fateen, Dahlia. "Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis". . p. 1354 - 1360. Retrieved 2014/03/21.