5166-53-0

Basic information

• Product Name: 5-METHYL-3-HEXEN-2-ONE
• Synonyms: 5-METHYL-3-HEXEN-2-ONE;5-METHYLHEX-3-EN-2-ONE;FEMA 3409;5-METHYL-3-HEXEN-2-ONE, TECH., 80%;3-Hexen-2-one, 5-methyl-;3-HEXAN-2-ONE,5-METHYL;5-Methyl-3-hexene-2-one;5-Methyl-2-oxohex-3-ene
• CAS NO: 5166-53-0
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• EINECS: 225-950-5
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 5166-53-0.mol

Chemical Properties

• Boiling Point: 157°C
• Flash Point: 118 °F
• Appearance: /
• Density: 0.85 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.8mmHg at 25°C
• Refractive Index: n20/D 1.44(lit.)
• CAS DataBase Reference: 5-METHYL-3-HEXEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-3-HEXEN-2-ONE(5166-53-0)
• EPA Substance Registry System: 5-METHYL-3-HEXEN-2-ONE(5166-53-0)

Safety Data

• Hazard Codes: Xn,T
• Statements: 10-20/21/22-24-20/22
• Safety Statements: 16-27-36/37/39-45-36/37
• RIDADR: UN 1992 3/PG 3
• WGK Germany: 3
• RTECS: MP8750000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 5166-53-0(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
5-METHYL-3-HEXEN-2-ONE is used as a flavoring agent for its characteristic green, leafy, and slightly fruity aroma. It is commonly added to food products to enhance their natural flavors, particularly in products that aim to replicate the taste of green vegetables or fruits.
Used in Chemical Synthesis:
5-METHYL-3-HEXEN-2-ONE is used as a key intermediate in the combinatorial synthesis of mercaptoketones and mercaptoalcohols. These synthesized compounds have various applications in the chemical industry, including the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 5-METHYL-3-HEXEN-2-ONE is often utilized in research and development for the creation of new compounds and materials. Its ability to react with indole in the presence of pyrrolidine and p-TsOH in CH2Cl2 to yield the 3-substituted indole adduct makes it a valuable compound for exploring new chemical reactions and applications.
Occurrence:
5-METHYL-3-HEXEN-2-ONE is naturally found in a variety of food items, including roasted filberts, green tea, and cooked and roasted shrimp. Its presence in these products contributes to their distinct flavors and aromas, making it an important compound in the food industry.

InChI:InChI=1/C7H12O/c1-6(2)4-5-7(3)8/h4-6H,1-3H3

Upstream product

• 65651-63-0 4-hydroxy-5-methyl-hexan-2-one 
• 78-84-2 isobutyraldehyde 
• 67-64-1 acetone 
• 56161-54-7 2-methyl-2-(2-(phenylsulfonyl)ethyl)-1,3-dioxolane 
• 75-26-3 isopropyl bromide 
• 98428-27-4 5-isopropyl-3-methyl-4,5-dihydro-1H-pyrazole 
• 18815-73-1 methylzinc iodide 
• 7553-56-2 iodine 
• 60-29-7 diethyl ether 
• 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 
• 75-36-5 acetyl chloride 
• 876-27-7 4-chlorophenyl acetate 

Downstream Products

• 28332-44-7 5-methylhex-4-en-2-one 
• 10321-71-8 4-methyl-pent-2-enoic acid 
• 759-05-7 3-methyl-2-ketobutanoic acid 
• 110-12-3 5-Methyl-2-hexanone 
• 18456-87-6 5-isopropyl-1,3-cyclohexanedione 
• 79083-88-8 4-(4-Chloro-phenyl)-5-methyl-hexan-2-one 
• 79083-91-3 1,4-Bis-(4-chloro-phenyl)-3-isopropyl-5-methyl-1H-pyrazole 
• 64-19-7 acetic acid 
• 79-31-2 isobutyric Acid 
• 15934-57-3 3-phenyl-4-methylpentan-2-one 
• 120609-18-9 (+/-)-5-methyl-4-phenylhexan-2-one 
• 85358-12-9 (5β,7α,8aβ)-4-amino-5-chloro-2-methoxy-N-(octahydro-5-isopropylindolizin-7-yl)benzamide 
• 85358-12-9 (5α,7α,8aβ)-4-amino-5-chloro-2-methoxy-N-(octahydro-5-isopropylindolizin-7-yl)benzamide 
• 85358-11-8 4-Acetylamino-5-chloro-N-((5R,7S,8aR)-5-isopropyl-octahydro-indolizin-7-yl)-2-methoxy-benzamide 

Relevant articles and documents

Sc(OTf)3a'Catalyzed Ca'C Bond-Forming Reaction of Cyclic Peroxy Ketals for the Synthesis of Highly Functionalized 1,2-Dioxene Endoperoxides

A new and general Sc(OTf)3-catalyzed C-C bond-forming reaction of 3-(2-methoxyethoxy)-endoperoxy ketals with silyl ketene acetals, silyl enol ethers, allyltrimethylsilane, and trimethylsilyl cyanide has been developed via the reactive peroxycarbenium ions, affording a wide range of complicated 3,3,6,6-tetrasubstituted 1,2-dioxenes bearing adjacent quaternary carbons and 3-acetyl/allyl/cyano functional groups in good yields at room temperature. Notably, the resultant 1,2-dioxenes are structurally stable, which can be facially transformed into another important 1,2-dioxane endoperoxide under conventional hydrogenation conditions without deconstructing the weak O-O bond.

Discovery and optimization of novel benzothiophene-3-carboxamides as highly potent inhibitors of Aurora kinases A and B

Aurora kinases as regulators of cell division have become promising therapeutic targets recently. Here we report novel, low molecular weight benzothiophene-3-carboxamide derivatives designed and optimized for inhibiting Aurora kinases. The most effective compound 36 inhibits Aurora kinases in vitro in the nanomolar range and diminishes HCT 116 cell viability blocking cytokinesis and inducing apoptosis. According to western blot analysis, the lead molecule inhibits Aurora kinases equipotently to VX-680 (Tozasertib) and similarly synergizes with other targeted drugs.

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.

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).

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.

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.

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

Unusual enantioselectivities in heterogeneous organocatalyzed reactions: Reversal of direction using proline di- versus tri-peptides in the aldol addition

The heterogeneous asymmetric direct aldol reactions between aldehydes (2-nitrobenzaldehyde, 2-methylpropanal) and ketones (acetone, cyclohexanone) in the presence of polystyrene (PS) resin supported di- and tripeptides were studied under otherwise identic

Improved conditions for the proline-catalyzed aldol reaction of acetone with aliphatic aldehydes

The proline-catalyzed asymmetric aldol reaction between aliphatic aldehydes and acetone has, to date, remained underdeveloped. Challenges in controlling this reaction include avoiding undesired side reactions such as aldol condensation and self-aldolization. In recent years we have developed optimized conditions, which enable high yields and good to excellent enantioselectivities, and which are presented in this communication. Georg Thieme Verlag Stuttgart New York.

Reversal of enantioselectivity in aldol reaction: New data on proline/λ-alumina organic-inorganic hybrid catalysts

We report new results on the aldol reactions between aldehydes of three different types (aromatic, aliphatic and cycloaliphatic) and acetone/cycloalkanones as reaction partners, driven by organic-inorganic hybrid catalyst Pro/λ-Al2O3. In contrast to the homogeneous liquidphase reaction, over Pro/λ-Al2O 3reversal of the enantioselection in up to 20-40 % ee depending on the structure of the aldehyde was observed in reactions of acetone. Reversal of the ee in the presence of c-Al2O3cannot be generalized, as it has only been observed for acetone among the ketones studied by us. It was proven using methods of a great variety such as ultrasonic irradiation, reuse measurements on used catalyst and the filtrate of the first reaction, measurements on the L-Pro-L-Pro(OH) dipeptide, studies using mixtures of L-Pro and D-Pro that the organic-inorganic hybrid catalyst Pro/λ-Al 2O3formed in situ is responsible for reversal of the ee. In the reactions of cycloalkanones there is presumably competition between the liquid-phase and the surface reaction over Pro/ c-Al2O 3with preference for the former. Based on these results a surface reaction pathway was proposed. Although, the ees obtained under heterogeneous catalytic conditions are low, further studies may lead to application of this unusual phenomenon for obtaining chiral heterogeneous catalysts suitable for the preparation of the desired enantiomer of a chiral compound using the same chiral source. Springer Science+Business Media New York 2013.