23267-57-4

Usage

Uses

Used in Flavor and Fragrance Industry:
4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-buten-2-one is used as a key compound for creating unique and complex fragrances and flavors. Its distinct chemical structure allows it to contribute to the development of novel scents and tastes, enhancing the sensory experience in various products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-buten-2-one is utilized as an intermediate in the synthesis of various drugs and medicinal compounds. Its unique chemical properties make it a valuable building block for developing new therapeutic agents.
Used in Chemical Research:
4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-buten-2-one serves as an important research tool in the field of organic chemistry. Its unique structure allows scientists to study various chemical reactions and mechanisms, leading to a better understanding of chemical processes and the development of new synthetic methods.
Used in Material Science:
In the field of material science, 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-buten-2-one can be used as a component in the development of novel materials with specific properties. Its unique chemical structure may contribute to the creation of materials with enhanced performance characteristics, such as improved stability, reactivity, or selectivity.
Overall, 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-buten-2-one is a versatile compound with a wide range of potential applications across various industries, including flavor and fragrance, pharmaceutical, chemical research, and material science. Its unique chemical structure and properties make it a valuable asset in the development of new products and technologies.

InChI:InChI=1/C13H20O2/c1-10(14)6-9-13-11(2,3)7-5-8-12(13,4)15-13/h6,9H,5,7-8H2,1-4H3

Upstream product

• 79-77-6 (E)-β-ionone 
• 54795-77-6 β-ionone 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 

Downstream Products

• 65869-04-7 4-(1,2,2-Trimethyl-6-oxo-cyclohexyl)butan-2-on 
• 55955-46-9 hydroxyionone 
• 65912-37-0 (E)-4-(1,2,2-Trimethyl-6-oxo-cyclohexyl)-but-3-en-2-on 
• 65868-84-0 (Z)-4-(1,2,2-Trimethyl-6-oxo-cyclohexyl)but-3-en-2-on 

Relevant academic research and scientific papers

A further step to sustainable palladium catalyzed oxidation: Allylic oxidation of alkenes in green solvents

The palladium catalyzed oxidation of alkenes with molecular oxygen is a synthetically important reaction which employs palladium catalysts in solution; therefore, a solvent plays a critical role for the process. In this study, we have tested several green solvents as a reaction medium for the allylic oxidation of a series of alkenes. Dimethylcarbonate, methyl isobutyl ketone, and propylene carbonate, solvents with impressive sustainability ranks and very scarcely exploited in palladium catalyzed oxidations, were proved to be excellent alternatives for the solvents conventionally employed in these processes, such as acetic acid. Palladium acetate alone or in the combination with p-benzoquinone efficiently operates as the catalyst for the oxidation of alkenes by dioxygen under 5–10 atm. For most substrates, the systems in green solvents showed better selectivity for allylic oxidation products as compared to pure acetic acid; moreover, the reactions in propylene carbonate solutions occurred even faster than in acetic acid.

Sustainable catalytic protocols for the solvent free epoxidation and: Anti -dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H2O2 as oxidant

A tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and α-pinene oxide on a multigram scale, with the catalyst being recycled three times to produce 3-carene oxide. Epoxidation of the less reactive disubstituted alkene bonds of terpene substrates could be achieved by carrying out catalytic epoxidation reactions at 50 °C. Methods have been developed that enable direct epoxidation of untreated crude sulfate turpentine to afford 3-carene oxide, α-pinene oxide and β-pinene oxide. Treatment of crude epoxide products (no work-up) with a heterogeneous acid catalyst (Amberlyst-15) results in clean epoxide hydrolysis to afford their corresponding terpene-anti-diols in good yields.

Synthesis, structural characterization and effect on human granulocyte intracellular cAMP levels of abscisic acid analogs

The phytohormone abscisic acid (ABA), in addition to regulating physiological functions in plants, is also produced and released by several mammalian cell types, including human granulocytes, where it stimulates innate immune functions via an increase of the intracellular cAMP concentration ([cAMP]i). We synthesized several ABA analogs and evaluated the structure-activity relationship, by the systematical modification of selected regions of these analogs. The resulting molecules were tested for their ability to inhibit the ABA-induced increase of [cAMP]i in human granulocytes. The analogs with modified configurations at C-2′ and C-3′ abrogated the ABA-induced increase of the [cAMP]i and also inhibited several pro-inflammatory effects induced by exogenous ABA on granulocytes and monocytes. Accordingly, these analogs could be suitable as novel putative anti-inflammatory compounds.

Synthesis and in vitro characterization of ionone-based compounds as dual inhibitors of the androgen receptor and NF-κB

Current therapeutic strategy for advanced prostate cancer is to suppress the androgen receptor (AR) signaling. However, lethal castration-resistant prostate cancer (CRPC) arises due to AR reactivation via multiple mechanisms, including mutations in the AR and cross-talk with other pathways such as NF-κB. We have previously identified two ionone-based antiandrogens (SC97 and SC245), which are full antagonists of the wild type and the clinically-relevant T877A, W741C and H874Y mutated ARs. Here, we discovered SC97 and SC245 also inhibit NF-κB. By synthesizing a series of derivatives of these two compounds, we have discovered a novel compound 3b that potently inhibits both AR and NF-κB signalling, including the AR F876L mutant. Compound 3b showed low micromolar antiproliferative activites in C4-2B and 22Rv1 cells, which express mutated ARs and are androgen-independent, as well as DU-145 and PC-3 cells, which exhibit constitutively activated NF-κB signalling. Our studies indicate 3b is effective against the CRPC cells.

Non-heme iron catalysis in CC, C-H, and CH2 oxidation reactions. Oxidative transformations on terpenoids catalyzed by Fe(bpmen)(OTf)2

The oxidation of terpene olefins with hydrogen peroxide in the presence of the non-hemo catalyst 5a afforded mixtures of epoxides whose composition was dependent upon the oxidation protocol used in each case. With terpenoid enones, the mixtures obtained evolved from clean epoxidation of α-ionone 23 to the clean allylic oxidation of damascone 28 due to the progressive deactivation of the electron density on the double bonds present in this series. The oxidation of bicyclic and tricyclic terpenoids afforded oxidation products coming from epoxidation, to olefin degradation, methyne and methylene activation products. Probably, the most attractive result was the synthesis of the Magnus lactone 46, from the tricyclic ether 45, with 88% yield and 100% conversion.

A short and efficient regioselective approach to the C-6 to C-19 segment of bifurcaranes and a formal total synthesis of β-microbiotene, microbiotol and cyclocuparanol

Employing an epoxide rearrangement based ring contraction reaction, a short and efficient regioselective approach to the C-6 to C-19 segment of the toluquinol substituted diterpenes bifurcaranes, and its extension to a formal total synthesis of the sesquiterpenes (±)-β-microbiotene, (±)-microbiotol and (±)-cyclocuparanol are described. The Royal Society of Chemistry 1999.

Facile and Regioselective Epoxidations of Olefins with a Peroxysulfur Intermediate Generated from Superoxide Anion (O2-.) and Nitrobenzenesulfonyl Chlorides

A peroxysulfur intermediate generated from the reaction of o- or p-nitrobenzenesulfonyl chloride with superoxide anion (O2-.) is found to be an excellent oxidizing reagent for the facile and regioselective epoxidation of olefins at -35 deg C.