Dihydrojasmone

Base Information

• Chemical Name: Dihydrojasmone
• CAS No.: 1128-08-1
• Deprecated CAS: 30966-11-1
• Molecular Formula: C11H18O
• Molecular Weight: 166.263
• Hs Code.: 29142990
• European Community (EC) Number: 214-434-5
• NSC Number: 71928
• UNII: Y953R7PP90
• DSSTox Substance ID: DTXSID4051584
• Nikkaji Number: J12.280G
• Wikipedia: Dihydrojasmone
• Wikidata: Q1225162
• Metabolomics Workbench ID: 44956
• ChEMBL ID: CHEMBL3728427
• Mol file: 1128-08-1.mol

Synonyms:3-methyl-2-(n-pentanyl)-2-cyclopenten-1-one

Chemical Property of Dihydrojasmone

Chemical Property:

• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 251.7 °C at 760 mmHg
• Flash Point: 110 °C
• PSA: 17.07000
• Density: 0.915 g/cm³
• LogP: 3.24610
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 166.135765193
• Heavy Atom Count: 12
• Complexity: 201

Purity/Quality:

99% ^*data from raw suppliers

Dihydrojasmone >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC1=C(CCC1=O)C

Technology Process of Dihydrojasmone

There total 282 articles about Dihydrojasmone 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%

6-methyl-n-pentyl-6-((trifluoromethyl)sulfonyl)tetra-hydrothiopyran-3-one 1,1-dioxide (96247-12-0) → dihydro-cis-jasmone (1128-08-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; for 3h; Heating;

DOI:10.1021/jo00212a020

Reference yield: 100.0%

1-methyl-2-pentyl-cyclopent-2-enol (386224-25-5,596100-84-4) → dihydro-cis-jasmone (1128-08-1)

Guidance literature:

With laccase from Trametes versicolor; oxygen; 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In dimethyl sulfoxide; at 30 ℃; for 3h; under 760.051 Torr; pH=5.2; Schlenk technique; Enzymatic reaction;

DOI:10.1002/adsc.201800299

Reference yield: 100.0%

3-methyl-2-(trans-1-pentenyl)-2-cyclopenten-1-one (87506-04-5) → dihydro-cis-jasmone (1128-08-1)

Guidance literature:

With hydrogen; platinum(IV) oxide; In methanol; at 20 ℃; atmospheric pressure;

DOI:10.1016/j.tet.2006.07.107

upstream raw materials:

5-hexyl-5-methyldihydro-2(3H)-furanone

undecane-2,5-diol

2,5-Undecanedione

3-Ethoxycarbonyl-4-methyl-dec-3-en-saeure-⁽¹⁾

Downstream raw materials:

3-methyl-2-pentyl-cyclopent-2-enone-(2,4-dinitro-phenylhydrazone)

levulinic acid

3,4-dihydro-5-methyl-6-pentyl-2H-pyran-2-one

4-Nitro-benzoic acid (1R,2R,5S)-5-methyl-1-pentyl-6-oxa-bicyclo[3.1.0]hex-2-yl ester

Refernces

• 1、 Brown, Herbert C.,Basavaiah, D.,Racherla, Uday S.. "Synthetic Applications of Organoboranes: A Simple Synthesis of Dihydrojasmone". . p. 886 - 888. Retrieved 1983.
• 2、 Gaoni. "". . p. 3277. Retrieved 1978.
• 3、 Stille, J.K.,Sweet, Mark P.. "Coupling Reactions of 1-Tributylstannyl-1-octen-3-ol Catalyzed by Palladium: The Synthesis of PGB1 and Coriolic Acid". . p. 3645 - 3648. Retrieved 1989.
• 4、 Ficini,J. et al.. "". . p. 1569 - 1571. Retrieved 1971.
• 5、 Ellison,Woessner. "". . p. 529. Retrieved 1972.
• 6、 Smith III,Branca,Pilla,Guaciaro. "Stereocontrolled total synthesis of (±)-pentenomycins I-III, their epimers, and dehydropentenomycin I". . p. 1855 - 1869. Retrieved 1982.
• 7、 Crawford,Rautenstrauch,Uijttewaal. "A new synthesis of methyl 3-oxo-2-pentyl-1-cyclopentene-1-acetate". . p. 1127 - 1128. Retrieved 2001.
• 8、 LaForge,Haller. "-". . p. 1777,1779. Retrieved 1936.
• 9、 Donkervoort, Johannes G.,Gordon, Alison R.,Johnstone, Craig,Kerr, William J.,Lange, Udo. "Development of modified Pauson-Khand reactions with ethylene and utilisation in the total synthesis of (+)-taylorione". . p. 7391 - 7420. Retrieved 1996.
• 10、 Nokami et al.. "". . p. 1047. Retrieved 1979.