(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:

99%, ^*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

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

(R)-4-acetoxycyclopent-2-en-1-one

(S)-4-oxocyclopent-2-en-1-yl acetate

1,3-cyclopentadione

Refernces

• 1、 Jaroszewski,Olafsdottir. "Natural glycosides of cyclopentenone cyanohydrins: Revised structure of so-called epitetraphyllin B". . p. 5297 - 5300. Retrieved 1986.
• 2、 Russell,Reay. "". . p. 1373,1376,1377. Retrieved 1971.
• 3、 Le Goff, Géraldine,Adelin, Emilie,Arcile, Guillaume,Ouazzani, Jamal. "Total synthesis of the antibiotic 4-hydroxycyclopent-2-en-1-one acrylate derivative EA-2801". . p. 2337 - 2339. Retrieved 2017.
• 4、 Morah, Frank N. I.. "TETRAPHYLLIN B FROM ADENIA CISSAMPELOIDES". . p. 2985 - 2986. Retrieved 1988.
• 5、 Garcia Ruano, Jose L.,Soriano, Jose F.,Fraile, Alberto,Martin, M. Rosario,Nunez, Alberto. "Regio-and stereoselective synthesis of pyrrolo or azepine-fused cyclopenta[ d ]isoxazolines from 2- p -tolylsulfinylcyclopent-2-en-1-one". . p. 17 - 32. Retrieved 2013.
• 6、 Asami, Masatoshi. "AN ASYMMETRIC SYNTHESIS OF CIS-4-t-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-OL AND CIS-4-TETRAHYDROPYRANYLOXY-2-CYCLOPENTEN-1-OL, VERSATILE CHIRAL SYNTHETIC INTERMEDIATE FOR PROSTANOIDS". . p. 5803 - 5806. Retrieved 1985.
• 7、 Truax, Nathanyal J.,Ayinde, Safiat,Van, Khoi,Liu, Jun O.,Romo, Daniel. "Pharmacophore-Directed Retrosynthesis Applied to Rameswaralide: Synthesis and Bioactivity of Sinularia Natural Product Tricyclic Cores". . p. 7394 - 7399. Retrieved 2019.
• 8、 Deng, Qiang,Deng, Shuguang,Gao, Rui,Li, Xiang,Lu, Chenxi,Tong, Zhikun,Wang, Jun,Yu, Lian,Zeng, Zheling,Zou, Ji-Jun. "Double-metal cyanide as an acid and hydrogenation catalyst for the highly selective ring-rearrangement of biomass-derived furfuryl alcohol to cyclopentenone compounds". . p. 2549 - 2557. Retrieved 2020.
• 9、 Alsters, Paul L.,Chou, Khi Chhay,De Wildeman, Stefaan M. A.,Faber, Teresa,Hadavi, Darya,Han, Peiliang,Quaedflieg, Peter J. L. M.,Schwalb Freire, Alfonso J.,Verzijl, Gerard K. M.,van Slagmaat, Christian A. M. R.. "Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts". supporting information. p. 10102 - 10112. Retrieved 2021/08/03.
• 10、 Bertonha, Ariane F.,Ho, Matthew,Ingros, Alec,Kim, Minwoo,Reisenauer, Keighley,Robinson, Joshua,Romo, Daniel,Svatek, Haleigh,Taube, Joseph,Xue, Haoran. "Synthesis of agelastatin A and derivatives premised on a hidden symmetry element leading to analogs displaying anticancer activity". supporting information. . Retrieved 2021/08/04.