10408-15-8

Basic information

• Product Name: 6-methyl-6-hepten-2-one
• Synonyms: 6-methyl-6-hepten-2-one;6-Hepten-2-one, 6-Methyl-;6-Methylhept-6-en-2-one
• CAS NO: 10408-15-8
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• Mol File: 10408-15-8.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 169.4°Cat760mmHg
• Flash Point: 49.7°C
• Appearance: /
• Density: 0.826g/cm³
• Vapor Pressure: 1.55mmHg at 25°C
• Refractive Index: 1.421
• CAS DataBase Reference: 6-methyl-6-hepten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-6-hepten-2-one(10408-15-8)
• EPA Substance Registry System: 6-methyl-6-hepten-2-one(10408-15-8)

Safety Data

• Hazardous Substances Data: 10408-15-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 4263, 1982 DOI: 10.1016/S0040-4039(00)88720-1

InChI:InChI=1/C8H14O/c1-7(2)5-4-6-8(3)9/h1,4-6H2,2-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 50592-60-4 5-methylhex-5-enenitrile 
• 66569-58-2 6-acetoxy-6-methyl-heptan-2-one 
• 78-94-4 methyl vinyl ketone 
• 115-11-7 isobutene 
• 111285-97-3 6-Methyl-6-hepten-2-one dimethylhydrazone 
• 56-23-5 tetrachloromethane 
• 32779-60-5 6-methylhept-6-en-2-ol 
• 3756-30-7 1-iodo-2-methyl-2-propene 
• 29021-98-5 3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol 
• 13984-57-1 ethyl 5-oxohexanoate 
• 1318767-42-8 N-methoxy-N,5-dimethylhex-5-enamide 
• 75-16-1 methylmagnesium bromide 
• 73541-16-9 5-iodo-2-methylpent-1-en 

Downstream Products

• 598-07-2 3,7-dimethyl-1,7-octadien-3-ol 
• 71312-45-3 6-methyl-6-hepten-2-one tosylhydrazone 
• 79831-35-9 C₁₅H₂₂N₂O₂S 
• 96849-99-9 ethyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate 
• 127333-81-7 cis-4,8-dimethyl-2-(2-phenylethyl)-3,6,7,8-tetrahydro-2H-oxocin 

Relevant articles and documents

TRANSPOSITION D'OXY-COPE A TEMPERATURE AMBIANTE CATALYSEE PAR LE DICHLORURE DE PALLADIUM-BISBENZONITRILE.

Tertiary hexa-1,5-diene-3-ols substituted on the carbon 5 (1 ; R1, R3 H) are isomerized at room temperature into δ-ethylenic ketones 2 by using 0.1 molar equivalent of the entitled palladium (II) complex.The yield of the transformation is good and the stereoselectivity is higher than 90 percent.

Transformation of presumptive precursors to frontalin and ex-brevicomin by bark beetles and the West Indian sugarcane weevil (Coleoptera)

(Z)-6-Nonen-2-one (1) has recently been shown to be the biosynthetic precursor for the aggregation pheromone exo-brevicomin (2) in mountain pine beetle (MPB) males, Dendroctonus ponderosae (Hopkins). We tested the hypotheses that (1) 6-methyl-6-hepten-2-one (3) is the biosynthetic precursor for the aggregation pheromone frontalin (4) in the spruce beetle (SB), Dendroctonus rufipennis (Kirby), and (2) that frontalin and exo-brevicomin are produced from 3 and 1, respectively, only by beetles that utilize them as aggregation pheromones. Exposure of scolytids MPB, SB, pine engraver (PE), Ips pini (Say) and Ips tridens (Mannerheim) and West Indian sugar cane weevil (WISW), Metamasius hemipterus sericeus (Olivier) to deuterio- or protio-3 invariably resulted in the production of deuterio- or protio-4. Similarly, exposure of SB, WISW and I. tridens to 1 resulted in the production of 2. We were unable to demonstrate the presence of 3 in SB volatiles, nor were we able to demonstrate the conversion of 6-methyl-5-hepten-2-one to 3 by SB. Production of enantiomerically enriched frontalin and exo-brevicomin by all the beetles exposed to respective precursors reveals widespread occurrence of nonspecific polysubstrate monooxidases in the Coleoptera.

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REGIOSELECTIVE SYNTHESIS OF 1-OLEFINS BY PALLADIUM-CATALYZED HYDROGENOLYSIS OF TERMINAL ALLYLIC COMPOUNDS WITH AMMONIUM FORMATE

Various terminal allylic compounds such as allylic esters, phenyl esters, carbonates, chlorides, and vinyl epoxides react with ammonium or sodium formate to give 1-olefins with high regioselectivity by using palladium-tributylphosphine complex as a catalyst.The reaction offers a useful synthetic method for 1-olefins.

Stereoselective synthesis of substituted oxocene cores by Lewis acid promoted cyclization

Substituted oxocene derivatives have been synthesized by Lewis acid catalyzed reactions of ε-hydroxyalkene and substituted aromatic aldehydes. The Cu(OTf)2-bis-phosphine catalyzed reaction typically provides substituted dihydropyran derivatives through an olefin migration followed by a Prins cyclization. The corresponding reaction catalyzed by TMSOTf or BF3·OEt2 provided eight-membered cyclic ethers (oxocenes), selectively. This methodology provides convenient access to a variety of 2,4,8-trisubstituted oxocenes in good yields and excellent diastereoselectivities.

Ultrasound promoted synthesis of (±)-8-hydroxy-5-isopropyl-8-methyl- 6(E)-nonen-2-one ((±)-solanone hydrate) and 3,7-dimethyl-2(E),7- octadienylpropionate

A facile synthesis of the title compounds has been accomplished using Zn-Cu couple catalyzed conjugate addition of allylic halides to α,β- unsaturated ketones initiated by ultrasonic waves under aqueous conditions and Horner-Wittig reaction using ethyl α-dimethylphosphonoacetate and NaH as base in dry THF as the key steps in overall good yields.

Halonium ion-mediated reaction of unsaturated hydroperoxy acetals. Competition between the formation of cyclic peroxides and the migration of the methoxy (or hydroxy) group

Monoozonolyses of dienes 2 in methanol gave in each case the corresponding unsaturated α-methoxy hydroperoxides 3. Capture of 2-alkyl- substituted cyclohexanone oxides by methanol was highly diastereoselective, thereby providing exclusively the hydroperoxides derived from attack by methanol from the less hindered face of the carbonyl oxide intermediates. Halonium ion-mediated reactions of the hydroperoxides 3 gave the novel methoxy- or hydroxy-migrated products, together with the expected halogen- substituted 1,2-dioxanes and/or 1,2-dioxepanes, the composition of the product mixture being a function of the halogenating agent utilized and the structure of 3.