2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (R)-

Base Information

• Chemical Name: 2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (R)-
• CAS No.: 51154-96-2
• Deprecated CAS: 38733-05-0
• Molecular Formula: C10H16O2
• Molecular Weight: 168.236
• Hs Code.: 2932999099
• European Community (EC) Number: 610-624-0
• UNII: 847O2V0IOA
• DSSTox Substance ID: DTXSID30885943
• Nikkaji Number: J11.190B
• Wikipedia: Massoia_lactone
• Wikidata: Q6784821
• ChEMBL ID: CHEMBL3126829
• Mol file: 51154-96-2.mol

Synonyms:51154-96-2;Massoya lactone;2H-PYRAN-2-ONE, 5,6-DIHYDRO-6-PENTYL-, (R)-;(R)-2-decen-5-olide;Cocolactone;(2R)-2-pentyl-2,3-dihydropyran-6-one;2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (6R)-;UNII-847O2V0IOA;847O2V0IOA;5-17-09-00218 (Beilstein Handbook Reference);(R)-(-)Massoialactone;BRN 4177048;(R)-(-)-Massoilactone;5,6-Dihydro-6-pentyl-2H-pyran-2-one, (R)-;(R)-cocolactone;NSC-721360;5-Hydroxy-2-decenoic acid .delta.-lactone;Natural Delta decalactone;2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (theta)-;(-)-MASSOILACTONE;(-)-MASSOIALACTONE;5-Pentylpent-2-en-5-olide;SCHEMBL8164022;(-)-MASSOJA DECALACTONE;CHEMBL3126829;DTXSID30885943;(-)-(6R)-MASSOIALACTONE;(6R)-(-)-MASSOIALACTONE;MFCD00801027;AKOS006272282;NSC 721360;(6r)-6-pentyl-5,6-dihydro-2h-pyran-2-one;(R)-6-pentyl-5,6-dihydro-2H-pyran-2-one;(6R)-5,6-dihydro-6-pentyl-2H-pyran-2-one;6-Pentyl-5,6-dihydro-2H-pyran-2-one, (6R)-;5,6-Dihydro-6-pentyl-(2H)-pyran-2-one-, (R);5-HYDROXY-2-DECENOIC ACID .DELTA.-LACTONE [FHFI]

Chemical Property of 2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (R)-

Chemical Property:

• Vapor Pressure: 0.00254mmHg at 25°C
• Refractive Index: 1.458
• Boiling Point: 287 °C at 760 mmHg
• Flash Point: 115.8 °C
• PSA: 26.30000
• Density: 0.964 g/cm³
• LogP: 2.43840
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

99%, ^*data from raw suppliers

(R)-2-DECEN-5-OLIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC1CC=CC(=O)O1
• Isomeric SMILES: CCCCC[C@@H]1CC=CC(=O)O1
• Description: 5-Hydroxy-2-decenoic acid δ-lactone has a sweet, lactonic, herbaceous odor with celery jasmine notes.

Technology Process of 2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (R)-

There total 110 articles about 2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (R)- 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: 86.0%

(R)-non-1-en-4-yl acrylate (263238-28-4) → (R)-massoialactone (51154-96-2,54814-64-1)

Guidance literature:

With Grubbs catalyst first generation; titanium(IV) isopropylate; In dichloromethane; Reflux; Inert atmosphere;

DOI:10.1055/s-0030-1260051

Reference yield: 82.0%

(2Z,5R)-dec-2-ene-1,5-diol (1298100-56-7) → (R)-massoialactone (51154-96-2,54814-64-1)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0032-1318440

Reference yield: 61.0%

trimetylsilylketene (4071-85-6) + (3R)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}octanal (220484-17-3) → (R)-massoialactone (51154-96-2,54814-64-1)

Guidance literature:

trimetylsilylketene; (3R)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}octanal; With ethylaluminum dichloride; In diethyl ether; hexane; at -45 - -30 ℃; for 2h;

With hydrogen fluoride; In acetonitrile; at 50 ℃; for 4h; Further stages.;

DOI:10.1016/j.tet.2003.11.094

upstream raw materials:

carbon dioxide

(2R,4S)-2-Pentyl-4-trimethylsilanyl-cyclopentanone

(R)-tert-butyl-(Z)-5-hydroxy-2-decenoate

(4R,6R)-4-hydroxy-6-pentyltetrahydro-2H-pyran-2-one

Downstream raw materials:

(R)-δ-decalactone

Refernces

• 1、 Romeyke, Yvonne,Keller, Martin,Kluge, Heinz,Grabley, Susanne,Hammann, Peter. "SECONDARY METABOLITES BY CHEMICAL SCREENING - 13. ENANTIOSELECTIVE SYNTHESIS OF δ-LACTONES FROM STREPTENOL A, A CHIRAL BUILDING BLOCK FROM STREPTOMYCES". . p. 3335 - 3346. Retrieved 1991.
• 2、 Marion,Le Fol,Courillon,Malacria. "One-pot diastereoselective preparation of α,β-unsaturated-γ-silylated-δ-lactones: Application towards natural compounds". . p. 138 - 140. Retrieved 2001.
• 3、 Bonini,Pucci,Racioppi,Viggiani. "Enzyme catalysed lactonization of 3,5 dihydroxy esters: Enantioselective synthesis of naturally occurring 3-hydroxy-5-decanolide, (-)-massoialactone, and 3-hydroxy-5-icosanolide". . p. 29 - 32. Retrieved 1992.
• 4、 Matsumoto,Oohana,Hashimoto,Usuda,Shimoda,Ohshima,Suzuki,Togawa. "Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent". . p. 3981 - 3988. Retrieved 2018/06/15.
• 5、 Padarti, Akhil,Han, Hyunsoo. "Rationally Designed Chiral Synthons Enabling Asymmetric Z- and E-Selective Vinylogous Aldol Reactions of Aldehydes". supporting information. p. 1448 - 1452. Retrieved 2018/03/09.