16400-72-9

Basic information

• Product Name: massoialactone
• Synonyms: 2H-Pyran-2-one, 6-heptyl-5,6-dihydro-; 5-Heptyl-2-pentene-5-olide; 5-Hydroxy-2-dodecenoic acid lactone; 6-Heptyl-5,6-dihydro-2-pyrone; 6-Heptyl-5,6-dihydro-2H-pyran-2-one; 6-Heptyl-5,6-dihydropyran-2-one; delta-2-Dodecenolactone; 5-Hydroxy-2-dodecenoic acid delta-lactone
• CAS NO: 16400-72-9
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.286
• EINECS: 240-453-3
• Mol File: 16400-72-9.mol

Chemical Properties

• Boiling Point: 318.1°C at 760 mmHg
• Flash Point: 130.8°C
• Density: 0.946g/cm³
• Vapor Pressure: 0.000368mmHg at 25°C
• Refractive Index: 1.46
• CAS DataBase Reference: massoialactone(CAS DataBase Reference)
• NIST Chemistry Reference: massoialactone(16400-72-9)
• EPA Substance Registry System: massoialactone(16400-72-9)

Safety Data

• Hazardous Substances Data: 16400-72-9(Hazardous Substances Data)

Upstream product

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Relevant articles and documents

2H-pyran-2-ones from trichoderma viride and trichoderma asperellum

Volatiles emitted by the soil fungi Trichoderma viride 272 and Trichoderma asperellum 328 were collected by using the closed loop stripping analysis (CLSA) headspace technique, and the obtained extracts were analysed by GC/MS. Several alkyl- and alkenyl-2H-pyran-2-ones, including known compounds 6-pentyl-2H-pyran-2-one and (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and the new derivatives (E)-6-(pent-2-en-1-yl)-2H-pyran-2-one, 6-propyl-2H-pyran-2-one, and 6-heptyl-2H-pyran-2-one were found. The alkenyl derivative (E)-6-(hept-1-en-1- yl)-2H-pyran-2-one, previously tentatively identified from a marine Botrytis by MS analysis, was also detected. All alkenyl pyrones were synthesised by using a reported Stille coupling followed by lactonisation, whereas the alkylated pyrones were obtained through a reported synthetic approach by radical bromination of 5-alkylpent-2-en-5-olides and dehydrobromination. Because the yields in both cases were not satisfactory and fell a long way short of the yields reported for similar compounds, all compounds were synthesised again using a gold-catalysed coupling of terminal alkynes with propiolic acid recently developed by Schreiber and co-workers, giving high yields in all cases. A comparison of the synthetic methods is given. Copyright

Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions

A copper-catalyzed desaturation method that is suitable for converting lactones, lactams, and cyclic ketones to their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium reagents and can be carried out through a simple one-step operation. The protocol uses inexpensive catalysts and reagents and exhibits excellent scalability and functional group tolerance. Notably, tert-butyl alcohol is the only stoichiometric byproduct produced, and overoxidation is not observed. The reaction mechanism has been investigated through control experiments, deuterium labeling, radical clock, electron paramagnetic resonance, high-resolution mass spectrometry, and kinetic studies. The data obtained are consistent with a reaction pathway involving reversible α-deprotonation by a Cu(II)-OtBu species followed by further oxidation of the resulting Cu enolate.

A NEW SYNTHESIS OF α,β-UNSATURATED γ- AND δ-LACTONS VIA INTRAMOLECULAR ACYLATION OF α-SULFINYL CARBANION

A new synthesis of α,β-unsaturated γ- and δ-lactones involving the intramolecular acylation of α-sulfinyl carbanion followed by pyrolisis is described.