6-Methyl-5-hepten-2-one

Base Information

• Chemical Name: 6-Methyl-5-hepten-2-one
• CAS No.: 110-93-0
• Deprecated CAS: 129085-68-3,132958-67-9
• Molecular Formula: C8H14O
• Molecular Weight: 126.199
• Hs Code.: 29141990
• European Community (EC) Number: 203-816-7
• NSC Number: 66569,15294
• UNII: 448353S93V
• DSSTox Substance ID: DTXSID5021629
• Nikkaji Number: J58.156I
• Wikipedia: Sulcatone
• Wikidata: Q3209146
• Metabolomics Workbench ID: 5445
• ChEMBL ID: CHEMBL46340
• Mol file: 110-93-0.mol

Synonyms:6-methyl-5-hepten-2-one;6-methylhept-5-ene-2-one;methylheptenone;sulcatone

Chemical Property of 6-Methyl-5-hepten-2-one

Chemical Property:

• Appearance/Colour: Clear slightly yellow liquid
• Vapor Pressure: 1.121hPa at 20℃
• Melting Point: -67.1 ºC
• Refractive Index: n20/D 1.439(lit.)
• Boiling Point: 173.3 ºC at 760 mmHg
• Flash Point: 50.6 ºC
• PSA: 17.07000
• Density: 0.835 g/cm³
• LogP: 2.32180
• Storage Temp.: Flammables area
• Solubility.: Soluble in methanol and chloroform.
• Water Solubility.: insoluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 126.104465066
• Heavy Atom Count: 9
• Complexity: 119

Purity/Quality:

99% ^*data from raw suppliers

6-Methyl-hepten-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10-36/37/38
• Safety Statements: 16-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: CC(=CCCC(=O)C)C
• Description: 6-Methyl-5-hepten-2-one has a strong, fatty, green, citrus-like odor, and a bittersweet taste reminiscent of pear. May be prepared from oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2C 03, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methylbuten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester.
• Uses: 6-Methyl-hepten-2-one is used in the synthesis of thyrsiferyl 23-Acetate which acts as an anti-leukemic inducer of apoptosis. Organic synthesis, inexpensive perfumes, fla-voring.

Technology Process of 6-Methyl-5-hepten-2-one

There total 164 articles about 6-Methyl-5-hepten-2-one 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: 95.8%

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) + 2-methyl-but-3-yn-2-ol (115-19-5) → 6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) + acetone (67-64-1)

Guidance literature:

potassium hydroxide; In water; at 93 ℃; for 6.41667h; Heating / reflux;

Reference yield: 92.0%

4-((E)-2,6-Dimethyl-hepta-1,5-dienyl)-morpholine → 4-morpholinecarboxaldehyde (4394-85-8) + 6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3)

Guidance literature:

With aluminum oxide; potassium permanganate; neutral; In acetone; for 4h; Ambient temperature;

DOI:10.1016/S0040-4039(96)02504-X

Reference yield: 61.0%

1,2-diamino-benzene (95-54-5) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8) → 2-Methyl-1H-benzimidazole (615-15-6) + 6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3)

Guidance literature:

With tetra(n-butyl)ammonium hydroxide; water; at 150 ℃; for 0.166667h; Microwave irradiation; Green chemistry;

DOI:10.1039/c4ra09932j

upstream raw materials:

1,5,5-trimethyl-2,6-dioxa-bicyclo[2.2.2]octan-3-one

1,3-dibromo-3-methylbutane

sodium acetylacetonate

6-methyl-3,5-heptadien-2-one

Downstream raw materials:

7-methyl-3,4-dimethyleneoct-6-en-2-one

(+/-)-lavandulol

3,7-dimethyl-octa-3,6-dienoic acid

6-methyl-hept-5-en-2-one-dimethylacetal

Refernces

• 1、 Esikova, I. A.,Yufit, S. S.. "REACTIONS OF CARBONYL COMPOUNDS IN THE PRESENCE OF PHASE TRANSFER CATALYSTS COMMUNICATION 12. ROLE OF QUATERNARY AMMONIUM CATION IN ALKYLATION OF ACETONE BY 1-CHLORO-3-METHYL-2-BUTENE". . p. 41 - 46. Retrieved 1983.
• 2、 Hall, Melanie,Hauer, Bernhard,Stuermer, Rainer,Kroutil, Wolfgang,Faber, Kurt. "Asymmetric whole-cell bioreduction of an α,β-unsaturated aldehyde (citral): competing prim-alcohol dehydrogenase and C-C lyase activities". . p. 3058 - 3062. Retrieved 2006.
• 3、 Pogrebnoi, S. I.,Kal'yan, Yu. B.,Krimer, M. Z.,Smit, V. A.. "-SIGMATROPIC REARRANGEMENTS OF THE ACETOACETATES OF ALLYL ALCOHOLS (CARROLL REACTION) AND ALLYLPHENYL ETHERS (CLAISEN REACTION) ON THE SURFACE OF ADSORBENTS". . p. 733 - 739. Retrieved 1991.
• 4、 Demyttenaere, Jan C.R.,De Footer, Herman L.. "Biotransformation of geraniol and nerol by spores of Penicillium italicum". . p. 1079 - 1082. Retrieved 1996.
• 5、 Muntyan,G.E. et al.. "-". . . Retrieved 1972.
• 6、 Voss, Constance V.,Gruber, Christian C.,Faber, Kurt,Knaus, Tanja,Macheroux, Peter,Kroutil, Wolfgang. "Orchestration of concurrent oxidation and reduction cycles for stereoinversion and deracemisation of sec-alcohols". . p. 13969 - 13972. Retrieved 2008.
• 7、 Moiseenkov, A. M.,Cheskis, B. A.,Kudryavtseva, G. A.,Nesmeyanova, O. A.,Semenovskii, A. V.. "PREPARATION OF CYCLOBUTANES VIA THE CYCLOPROPYLCARBINYL REARRANGEMENT". . p. 1396 - 1400. Retrieved 1982.
• 8、 Masaki,Yamada,Tanaka. "Novel polymer effect in cleavage reactions of acetals and silyl ethers in aqueous media catalyzed by a polymer-supported dicyanoketene acetal". . p. 1311 - 1313. Retrieved 2001.
• 9、 Fielder, Simon,Rowan, Daryl D.,Sherburn, Michael S.. "Synthesis of sesquiterpene polyene hydroperoxides by regio- and stereoselective transposition reactions". . p. 12907 - 12922. Retrieved 1998.
• 10、 Amico, Vincenzo,Oriente, Giovanna,Piattelli, Mario,Ruberto, Giuseppe,Tringali, Corrado. "A QUINONE-HYDROQUINONE COUPLE FROM THE BROWN ALGA CYSTOSEIRA STRICTA". . p. 421 - 424. Retrieved 1982.