1669-43-8

Basic information

• Product Name: 5-methyl-hex-3c-en-2-one
• Synonyms: 5-methyl-hex-3c-en-2-one
• CAS NO: 1669-43-8
• Molecular Weight: 112.172
• Mol File: 1669-43-8.mol

Chemical Properties

• CAS DataBase Reference: 5-methyl-hex-3c-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-hex-3c-en-2-one(1669-43-8)
• EPA Substance Registry System: 5-methyl-hex-3c-en-2-one(1669-43-8)

Safety Data

• Hazardous Substances Data: 1669-43-8(Hazardous Substances Data)

Upstream product

• 60-29-7 diethyl ether 
• 78-84-2 isobutyraldehyde 
• 67-64-1 acetone 
• 65651-63-0 4-hydroxy-5-methyl-hexan-2-one 
• 4376-49-2 1-isopropyl-2,3-butadien-1-ol 
• 59697-04-0 5-methyl-4-(toluene-4-sulfonyloxy)-hexan-2-one 
• 28332-44-7 5-methylhex-4-en-2-one 
• 541-50-4 2-acetoacetic acid 
• 75-36-5 acetyl chloride 
• 7553-56-2 iodine 
• 876-27-7 4-chlorophenyl acetate 
• 146513-95-3 (rac,E)-5-methylhex-3-en-2-ol 
• 67-56-1 methanol 
• 869096-24-2 9-tolylsulfonyl-4,9-dihydro-3H-β-carboline 

Downstream Products

• 75508-46-2 2-methyl-2-(3-methyl-but-3-enyl)-[1,3]dioxolane 
• 6611-92-3 5-methyl-4-hexen-2-one ethylene ketal 
• 75508-45-1 2-Methyl-2-((E)-3-methyl-but-1-enyl)-[1,3]dioxolane 
• 120609-18-9 (+/-)-5-methyl-4-phenylhexan-2-one 
• 40238-92-4 4-ethyl-5-methyl-hexane-2-one 
• 258833-04-4 (+)-4-Ethyl-5-methylhexan-2-one 
• 258833-04-4 (-)-4-Ethyl-5-methylhexan-2-one 
• 364043-00-5 3-isopropyl-5-oxo-1,1,2,2-cyclohexanetetracarbonitrile 
• 258833-04-4 (R)-4-ethyl-5-methylhexan-2-one 
• 258833-04-4 (S)-4-ethyl-5-methylhexan-2-one 
• 435269-66-2 (S)-5-methyl-4-phenylhexan-2-one 
• 162239-77-2 (R)-5-methyl-4-phenyl-hexan-2-one 
• 908302-28-3 (3E)-4-isopropyl-2-(triisopropylsiloxy)-1,3-butadiene 

Relevant articles and documents

Proline-catalyzed ketone-aldehyde aldol reactions are accelerated by water

Proline-catalyzed aldol reactions between acetone or 4-thianone and different aldehydes are accelerated by addition of 1-10 equivalents of water to the reaction medium, allowing stoichiometric aldol reactions to proceed at acceptable rates.

Oxidative asymmetric formal aza-Diels–Alder reactions of tetrahydro-β-carboline with enones in the synthesis of indoloquinolizidine-2-ones

Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels–Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4 + 2] cycloaddition, providing a step-economical strategy for the synthesis of these valuable heterocyclic products.

Catalytic Asymmetric Conjugate Addition of Indolizines to α,β-Unsaturated Ketones

A catalytic enantioselective conjugate addition of indolizines to enones is described. The chiral phosphoric acid (S)-TRIP activates α,β-unsaturated ketones, thereby promoting an enantioface-differentiating attack by indolizines. Using this reaction, several alkylated indolizines were synthesized in good yields and with enantiomeric ratios of up to 98:2.

PYRIDINETHIONES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR THERAPEUTIC USE FOR TREATING A PROLIFERATIVE, INFLAMMATORY, NEURODEGENERATIVE, OR IMMUNE-MEDIATED DISEASE

Provided herein are pyridinethiones, for example, a compound of Formula I, and pharmaceutical compositions thereof. Also provided herein are methods of their use for treating, preventing, or ameliorating one or more symptoms of a proliferative, inflammatory, neurodegenerative, or immune-mediated disease (e.g., multiple sclerosis).

Design, synthesis and biological evaluation of novel C3-functionalized oxindoles as potential Pim-1 kinase inhibitors

A novel series of C3-functionalized oxindoles, 3-(2-oxo-4-phenylbut-3-en-1-ylidene)indolin-2-ones, were designed, synthesized and investigated for inhibition of cell proliferation against different types of human cancer cell lines, including SW620, HeLa and A549. This biological study showed that these compounds containing the scaffolds of indole and aromatic α,β-unsaturated ketone had moderate to significant antitumor activities. Further study suggested that compound 4b, as one of this kind of structure derivative, showed broad-spectrum antitumor activities against MCF-7, PC-3, SKOV-3, U87, SMMC-7721, SY5Y and A875 cancer cell lines. Besides, the results of the inhibition of Pim kinases indicated that compound 4b showed selective and efficient anti-Pim-1 kinase activity (IC50 = 5 μM). Docking simulation, flow cytometry (FCM), and Hoechst 33342 staining assay suggested that the most active compound 4b induced cell death through apoptosis via binding to the active ATP pocket of Pim-1. Moreover, it showed that compound 4b had strong inhibition of tubulin polymerization which may be caused by inhibiting Pim-1. This journal is

Asymmetric Catalysis with Ethylene. Synthesis of Functionalized Chiral Enolates

Trialkylsilyl enol ethers are versatile intermediates often used as enolate surrogates for the synthesis of carbonyl compounds. Yet there are no reports of broadly applicable, catalytic methods for the synthesis of chiral silyl enol ethers carrying latent functionalities useful for synthetic operations beyond the many possible reactions of the silyl enol ether moiety itself. Here we report a general procedure for highly catalytic (substrate:catalyst ratio up to 1000:1) and enantioselective (92% to 98% major enantiomer) synthesis of such compounds bearing a vinyl group at a chiral carbon at the β-position. The reactions, run under ambient conditions, use trialkylsiloxy-1,3-dienes and ethylene (1 atm) as precursors and readily available (bis-phosphine)-cobalt(II) complexes as catalysts. The silyl enolates can be readily converted into novel enantiopure vinyl triflates, a class of highly versatile cross-coupling reagents, enabling the syntheses of other enantiomerically pure, stereodefined trisubstituted alkene intermediates not easily accessible by current methods. Examples of Kumada, Stille, and Suzuki coupling reactions are illustrated.

Large-scale synthesis of immunoactivating natural product, pristane, by continuous microfluidic dehydration as the key step

(Figure Presented) An efficient protocol of dehydration was developed under microfluidic conditions. The method was applied to a multikilogram synthesis of pristane, a biologically important natural product, which is now widely used as an adjuvant for monoclonal antibody production.

L-proline-catalyzed one-pot three-component reaction for the synthesis of β-alkoxy ketones

β-Alkoxy ketones were prepared by a one-pot three-component reaction of aliphatic aldehydes, ketones, and alcohols catalyzed by L-proline. Steric effects on the reaction were studied with substituted ketones, aldehydes, and alcohols, and the results indicate that reactions employing methyl ketones, α-unsubstituted aliphatic aldehydes and methanol produce the β-alkoxy ketones in the best yields when L-proline is used as the catalyst. The reaction mechanism is discussed. Georg Thieme Verlag Stuttgart.

Palladium catalyzed reductive decarboxylation of allyl α-alkenyl- β-ketoesters. A new synthesis of (E)-3-alkenones

The reductive decarboxylation of α-alkenyl derivatives of allyl-β-ketoesters was achieved by use of palladium(0) catalyst generated in situ from Pd(OAc)2 and PPh3, with triethylammonium formate as the hydride source, in THF. The reaction proceeds smoothly and cleanly, with linear alkenyl derivatives of allyl-β-ketoesters, to afford (E)-3-alkenones in good to excellent yields (73-92%) and high stereoselectivity (>98%).