136801-74-6

Upstream product

• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 98-88-4 benzoyl chloride 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 130573-43-2 (2,2-dimethyl-6-methylene-6H-1,3-dioxin-4-yloxy)trimethylsilane 
• 1304104-42-4 C₉H₁₆O₄Si 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 136801-83-7 6-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 

Downstream Products

• 5526-38-5 4-hydroxy-6-phenyl-2H-pyran-2-one 
• 136801-83-7 6-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 
• 857249-01-5 6-(1-benzoylpentyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 
• 857249-03-7 6-(1-benzoylhexyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 
• 857248-99-8 6-(1-benzoylpropyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 
• 1293991-75-9 3-[(1Z)-1-hydroxy-3-oxo-3-phenylprop-1-en-1-yl]-6,6,9a-trimethyl-5,6-dihydro-2H-furo[3,2-g]isochromene-2,9(9aH)-dione 
• 92687-12-2 6-(phenyl)-dihydro-2H-pyran-2,4(3H)-dione 
• 10225-39-5 2-butyl-1-phenyl-1,3-butanedione 
• 56745-75-6 2-pentyl-1-phenyl-1,3-butanedione 

Relevant academic research and scientific papers

A Biocatalytic Route to Highly Enantioenriched β-Hydroxydioxinones

A novel biocatalytic system to access a wide variety of β-hydroxydioxinones from β-ketodioxinones employing commercial engineered ketoreductases has been developed. This practical system provides a remarkably straightforward solution to limitations in acc

Design and synthesis of epicocconone analogues with improved fluorescence properties

Epicocconone is a natural latent fluorophore that is widely used in biotechnology because of its large Stokes shift and lack of fluorescence in its unconjugated state. However, the low photostability and quantum yields of epicocconone have limited its wid

Versatile synthesis of acylfuranones by reaction of acylketenes with α-hydroxy ketones: Application to the one-step multicomponent synthesis of cadiolide B and its analogues

Functionalized acylfuranones have been prepared in a one-step procedure by thermal fragmentation of the corresponding dioxinones in the presence of hydroxy ketones in basic conditions. Multicomponent reactions also occur on addition of an aldehyde as a third reaction partner resulting in an expeditious access to cadiolide B and its analogues. A new method for the synthesis of acylfuranones is described based on the fragmentation of dioxinones to acylketenes followed by trapping with hydroxy ketones. Addition of an aldehyde as a third reaction partner leads to a supplementary aldolization/crotonization sequence resulting in an expeditious synthesis of cadiolide B and its analogues. Copyright

4-AMINO-2H-PYRAN-2-ONE ANALOGS AS ANTICANCER AGENTS

Compounds of Formula I are described, along with methods of using such compounds for the treatment of cancer and pharmaceutical formulations thereof.

Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

4-Amino-2H-benzo[h]chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H- benzo[h]chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 μM.

Facile syntheses of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the corresponding 6-substituted 4-hydroxy-2-pyrones

A variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 5a-l and the corresponding 6-substituted 4-hydroxy-2-pyrones 3a-l were prepared in high yields under mild reaction conditions by the reaction of 2,2,6-trimethyl-1,3- dioxin-4-one 4 with 1-acylbenz

Synthesis of 6-substituted 4-hydroxy-2-pyrones from aldehydes by addition of an acetoacetate equivalent, Dess-Martin oxidation and subsequent cyclization

A three step procedure for the synthesis of 6-substituted 4-hydroxy-2-pyrones 2 from aldehydes 1 is described. An acetoacetate equivalent 3 was added to the corresponding aldehyde (10 examples) in a vinylogous Mukaiyama aldol addition (72-99%). The intermediate alcohols 4 were oxidized to the ketones 5 using the Dess-Martin method (67%-quant,). A final thermal cyclization of compounds 5 yielded the title compounds 2 (61-92%; 40-85% overall).

TWO LACTONE FORMATION REACTIONS FROM 1,3-DIOXIN-4-ONES HAVING HYDROXYALKYL GROUP AT THE 6-POSITION: DIFFERENCE IN RING OPENING AND CLOSURE

Two methods (A: ring opening to acylketenes followed by intramolecular ketene trapping and B: methoxide-mediated ring opening followed by cyclization of the hydroxy esters thus formed) have become available for the synthesis of lactones and/or cyclic ethers from 1,3-dioxin-4-ones having 1- 4-hydroxyalkyl group at the 6-position.Mechanism and scope of both methods have been clarified.