3-Hexyne-2-one (CAS: 1679-36-3): High purity organic synthesis intermediate
3-Hexyne-2-one is an important organic compound belonging to the alkyne ketone family. Its molecular structure contains two highly active functional groups, carbon carbon triple bond (alkynyl) and carbonyl (keto), making it a highly valuable intermediate in the field of organic synthesis.
Physical and chemical properties
Appearance: Colorless to pale yellow transparent liquid
Boiling point: 68 ℃ (50 mmHg)
Flash point: 39 ℃ (flammable)
Refractive index: 1.4410
Vapor pressure: 9.72 mmHg (25 ℃)
Storage conditions: Refrigerate (2-8 ℃), keep away from sources of fire, seal and store
Product Manager Email:ada@coreychem.com
Structural formula:
Main application areas
1. Organic synthesis intermediates
3-Hexyne-2-one is an important “building block” for constructing complex organic molecules, and its dual functional group structure of alkynyl and carbonyl groups endows it with diverse reactivity:
Nucleophilic addition reaction: Carbonyl groups can react with various nucleophilic reagents (such as alcohols and amines) to generate alcohol, ether, and amine derivatives
Cycloaddition reaction: Participate in the synthesis of nitrogen-containing and oxygen-containing heterocyclic compounds through cycloaddition reactions
Asymmetric reduction: can be used as a substrate for chiral reduction, for the synthesis of chiral propargyl alcohol
2. Biological activity research
Research has shown that 3-hexyne-2-one and its derivatives have significant biological activity potential:
Antibacterial activity: It has inhibitory effects on various pathogenic microorganisms, including:
Escherichia coli
Staphylococcus aureus
Candida albicans
Cytotoxicity: exhibiting inhibitory effects on multiple cancer cell lines:
HeLa cells (cervical cancer): IC ₅₀ ≈ 30 μ M
MCF-7 cells (breast cancer): IC ≮ ≈ 25 μ M
Research suggests that its cytotoxic mechanism may be related to inducing oxidative stress and disrupting mitochondrial membrane potential.
3. Medicinal Chemistry
As a precursor of drug molecules, 3-hexyne-2-one is being studied for:
Development of anti-cancer drugs
Lead compounds of new antibacterial agents
Synthesis of chiral drug intermediates
4. Organic functional materials
The alkyne ketone structure endows it with good reactivity and conjugation properties, and has promising applications in materials science
Organic optoelectronic material precursor
Conductive polymer monomer
Liquid crystal material intermediate
Reaction characteristics and research progress
1. Asymmetric Reduction Study: Studies have shown that 3-hexyne-2-one can be asymmetrically reduced using chiral boron reagents to generate the corresponding chiral propargyl alcohol
Using potassium salt of 9-O – (1,2,5,6-di-O-isopropylidene – α – D-furanosyl) -9-borabicyclo [3.3.1] nonane, the (R) – enantiomer can be obtained with an enantiomer excess of 34%
Using potassium borohydride with B-methoxydiisopropyl pine group, a 39% ee (R) – enantiomer can be obtained
2. Halogenation reaction: Reacts with bromochlorine (BrCl) and iodochloride (ICl) to mainly generate (Z) – anti Markovian (AM) region isomers, which are selectively attributed to the electronic and steric hindrance effects of carbonyl groups on triple bonds.
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