cis-3,5-Diacetoxy-1-cyclopentene

Base Information

• Chemical Name: cis-3,5-Diacetoxy-1-cyclopentene
• CAS No.: 54664-61-8
• Molecular Formula: C9H12O4
• Molecular Weight: 184.192
• Hs Code.: 2915390090
• European Community (EC) Number: 860-765-9
• DSSTox Substance ID: DTXSID50436532
• Nikkaji Number: J376.375G
• Wikidata: Q82251810
• Mol file: 54664-61-8.mol

Synonyms:cis-3,5-Diacetoxy-1-cyclopentene;54664-61-8;cis-4-(acetyloxy)cyclopent-2-en-1-yl acetate;[(1S,4R)-4-acetyloxycyclopent-2-en-1-yl] acetate;(1R,3S)-rel-Cyclopent-4-ene-1,3-diyl diacetate;cis-1,4-diacetoxycyclopent-2-ene;cis-3,5-diacetoxycyclopentene;cis-4-Cyclopentene-1,3-diol diacetate;rel-(1R,3S)-Cyclopent-4-ene-1,3-diyl diacetate;SCHEMBL254386;DTXSID50436532;UKPIBFMHHUEUQR-DTORHVGOSA-N;MFCD03002563;AKOS015910346;3alpha,5alpha-Diacetoxy-1-cyclopentene;AS-50441;P10241;[(1S,4R)-4-Acetoxycyclopent-2-en-1-yl]acetate;A830306;cis-3,5-Diacetoxy-1-cyclopentene, >=98.0% (GC);Acetic acid (1S,4R)-4-acetoxy-cyclopent-2-enyl ester

Chemical Property of cis-3,5-Diacetoxy-1-cyclopentene

Chemical Property:

• Vapor Pressure: 0.079mmHg at 25°C
• Refractive Index: n20/D 1.460
• Boiling Point: 227.098 °C at 760 mmHg
• Flash Point: 105.207 °C
• PSA: 52.60000
• Density: 1.15 g/cm³
• LogP: 0.80970
• Storage Temp.: 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 184.07355886
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

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

Cis-3,5-Diacetoxy-1-Cyclopentene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC(C=C1)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@@H]1C[C@@H](C=C1)OC(=O)C
• Uses: cis-3,5-Diacetoxy-1-cyclopentene may be employed as substrate to investigate the enantioselectivity of esterase EstA3 (obtained from a drinking water metagenome) and esterase EstCE1 (obtained from a soil metagenome).

Technology Process of cis-3,5-Diacetoxy-1-cyclopentene

There total 45 articles about cis-3,5-Diacetoxy-1-cyclopentene 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: 100.0%

vinyl acetate (108-05-4,9003-20-7) + cis-4-cyclopentene-1,3-diol (29783-26-4) → cis-1,4-diacetoxy-2-cyclopentene (54664-61-8)

Guidance literature:

With lipase from candida antartica; triethylamine; In tetrahydrofuran; at 20 ℃; for 0.5h; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.tetlet.2014.10.105

Reference yield: 99.0%

acetic anhydride (108-24-7) + cis-3-acetoxy-5-hydroxycyclopent-1-ene (61740-26-9) → cis-1,4-diacetoxy-2-cyclopentene (54664-61-8)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 22 ℃; for 19h;

DOI:10.1021/ol051415y

Reference yield: 97.0%

cis-4-cyclopentene-1,3-diol (29783-26-4) + acetic anhydride (108-24-7) → cis-1,4-diacetoxy-2-cyclopentene (54664-61-8)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4020(01)85571-X

upstream raw materials:

cis-3,5-dibromocyclopentene

tetraethylammonium acetate

silver(I) acetate

acetic acid

Downstream raw materials:

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

(1R,4R)-(+)-4-Hydroxy-2-cyclopentenyl acetate

Acetic acid (1R,4S)-4-benzyloxymethoxy-cyclopent-2-enyl ester

Acetic acid (E)-3-[(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

Refernces

• 1、 Krout, Michael R.,Henry, Christopher E.,Jensen, Thomas,Wu, Kun-Liang,Virgil, Scott C.,Stoltz, Brian M.. "Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin". . p. 6995 - 7009. Retrieved 2018.
• 2、 Ghorpade, Sandeep R.,Kharul, Rajendra K.,Joshi, Rohini R.,Kalkote, Uttam R.,Ravindranathan. "Desymmetrization of meso-cyclopenten-cis-1,4-diol to 4-(R)- hydroxycyclopent-2-en-1-(S)-acetate by irreversible transesterification using Chirazyme". . p. 891 - 899. Retrieved 1999.
• 3、 Mandai, Hiroki,Hironaka, Tsubasa,Mitsudo, Koichi,Suga, Seiji. "Acylative desymmetrization of cyclic meso-1,3-diols by chiral DMAP derivatives". supporting information. p. 471 - 474. Retrieved 2021/03/15.