(R)-4-Hydroxycyclopent-2-enone

Base Information

• Chemical Name: (R)-4-Hydroxycyclopent-2-enone
• CAS No.: 59995-47-0
• Molecular Formula: C5H6O2
• Molecular Weight: 98.1014
• Hs Code.: 2914400090
• DSSTox Substance ID: DTXSID50424919
• Nikkaji Number: J303.584K
• Wikidata: Q82237680
• Mol file: 59995-47-0.mol

Synonyms:(R)-4-Hydroxycyclopent-2-enone;59995-47-0;(4R)-(+)-Hydroxy-2-cyclopenten-1-one;(4R)-4-hydroxycyclopent-2-en-1-one;(R)-4-hydroxycyclopent-2-en-1-one;starbld0018235;4(r)-hydroxycyclopent-2-enone;DTXSID50424919;(4R)hydroxy-2-cyclopenten-1-one;4alpha-Hydroxy-2-cyclopentene-1-one;MFCD00134671;AKOS006272437;CS-0113091;A902034

Chemical Property of (R)-4-Hydroxycyclopent-2-enone

Chemical Property:

• Vapor Pressure: 0.00535mmHg at 25°C
• Refractive Index: 1.559
• Boiling Point: 243.7 °C at 760 mmHg
• PKA: 12.95±0.20(Predicted)
• Flash Point: 99.9 °C
• PSA: 37.30000
• Density: 1.299 g/cm³
• LogP: -0.12370
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 115

Purity/Quality:

97% ^*data from raw suppliers

(4R)-(+)-HYDROXY-2-CYCLOPENTEN-1-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C=CC1=O)O
• Isomeric SMILES: C1[C@H](C=CC1=O)O
• General Description: (4R)-(+)-Hydroxy-2-cyclopenten-1-one is a chiral cyclopentenone derivative that can be efficiently synthesized through chemoenzymatic methods, starting from 3-methoxycyclopent-2-en-1-one or renewable resources like furfuryl alcohol. It serves as a key intermediate in the synthesis of biologically active compounds, including the antibiotic EA-2801, and can be produced enantioselectively via enzymatic resolution or chiral separation techniques. Its synthesis has been optimized using microwave or microreactor-assisted methods, enabling scalable and sustainable production.

Technology Process of (R)-4-Hydroxycyclopent-2-enone

There total 125 articles about (R)-4-Hydroxycyclopent-2-enone 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: 99.0%

furfural (98-01-1) → 4-Hydroxycyclopent-2-enone (59995-47-0,59995-49-2,61305-27-9,61740-29-2)

Guidance literature:

With sodium hydroxide; In water; at 240 ℃; for 0.02h; Reagent/catalyst; Temperature; Time; Solvent;

Reference yield: 99.0%

(2-furyl)methyl alcohol (98-00-0,25212-86-6,93793-62-5) → 4-Hydroxycyclopent-2-enone (59995-47-0,59995-49-2,61305-27-9,61740-29-2)

Guidance literature:

With sodium hydroxide; In water; at 240 ℃; Temperature; Reagent/catalyst; Solvent; Autoclave;

Reference yield: 93.0%

(R)-4-oxocyclopenten-2-enyl 2-phenylacetate (1391630-29-7) → 4-Hydroxycyclopent-2-enone (59995-47-0,59995-49-2,61305-27-9,61740-29-2)

Guidance literature:

With water; In tert-butyl alcohol; at 20 ℃; for 10h; Enzymatic reaction;

DOI:10.1021/op400266k

upstream raw materials:

maleic anhydride

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone

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

tetraphyllin B

Downstream raw materials:

(-)-(1R,4S)-(1,4-dihydroxy-cyclopent-2-enyl)-acetic acid t-butyl ester

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

(4S)-4-(p-bromobenzoyloxy)-2-cyclopenten-1-one

4(S)-<(tert-butyldiphenylsilyl)oxy>cyclopent-2-en-1-one