136801-83-7

Upstream product

• 100-52-7 benzaldehyde 
• 588731-92-4 tert-butyl-(2,2-dimethyl-6-methylene-6H-[1,3]-dioxin-4-yloxy)dimethylsilane 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 1304104-42-4 C₉H₁₆O₄Si 
• 98-88-4 benzoyl chloride 
• 136801-74-6 2,2-dimethyl-6-(2-oxo-2-phenylethyl)-4H-1,3-dioxin-4-one 
• 130573-43-2 (2,2-dimethyl-6-methylene-6H-1,3-dioxin-4-yloxy)trimethylsilane 

Downstream Products

• 195376-12-6 2,2-Dimethyl-6-(2-phenyl-2-vinyloxy-ethyl)-[1,3]dioxin-4-one 
• 195376-07-9 Carbonic acid allyl ester 2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-1-phenyl-ethyl ester 
• 5526-38-5 4-hydroxy-6-phenyl-2H-pyran-2-one 
• 136801-74-6 2,2-dimethyl-6-(2-oxo-2-phenylethyl)-4H-1,3-dioxin-4-one 
• 92687-12-2 6-(phenyl)-dihydro-2H-pyran-2,4(3H)-dione 

Relevant academic research and scientific papers

Efficient and practical catalytic vinylogous aldol reaction of dioxinone-derived silyl dienol ethers with aromatic aldehydes

Vinylogous Mukaiyama-aldol reaction was realized by use of dioxinone-derived silyl dienol ethers and various aldehydes in the presence of highly catalytic amounts of bismuth triflate. The reaction proceeds rapidly and affords the corresponding β-hydroxy-1

Stereoselective synthesis of tetrahydropyran-4-ones from dioxinones catalyzed by scandium(III) triflate

(Chemical Equation Presented) A scandium triflate catalyzed, diastereoselective cyclization between aldehydes and β-hydroxy dioxinones has been discovered. This process capitalizes on the untapped nucleophilicity of the embedded enol ether within the dioxinone core. The bicyclic compounds from the resulting cyclization can be isolated, or alternatively, alkoxide nucleophiles can be directly added. This in situ addition fragments the dioxinone rings and delivers the 3-carboxy-substituted tetrahydropyran-4-ones in good yields with high levels of diastereoselectivity.

Solvent-free Mukaiyama aldol reaction of O-silyl dienolates catalyzed by benzoic acid

The vinylogous aldol reaction of O-silyl dienolates deriving from 2,2-dimethyl-[1,3]-dioxin-4-ones proceeds in moderate to excellent yields in the presence of catalytic amounts of PhCOOH under solvent-free conditions. Modest to good yields can be obtained by using silica gel or 3 ? molecular sieves as heterogeneous catalysts.

Mechanistic insights into Cu-catalyzed asymmetric aldol reactions: Chemical and spectroscopic evidence for a metalloenolate intermediate

In situ IR spectroscopy and transmetalation experiments confirm a postulated catalytic cycle. The metalloenolate 1 describes the active intermediate in the aldol reaction catalyzed by [CuF2{(S)-tol-binap}] (see reaction scheme). (S)-tol-binap =

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.

Silicon tetrachloride in organic synthesis: New applications for the vinylogous aldol reaction

This paper describes a novel and efficient methodology for vinylogous aldol reactions based on SiCl4 catalysis. According to the nucleophilicity Mayr's scale, vinylogous aldol reaction of Chan's diene proved to be effective by using catalytic amount of SiCl4, without any other promoter. On the contrary, the SiCl4/Lewis base system has been conveniently exploited for the efficient and selective vinylogous reaction of less nucleophilic Danishefsky's diene and 2-trimethylsilyloxyfuran (TMSOF). Indeed, a number of Lewis bases, such as sulfoxides, formamides and phosphoramides have been successfully used as SiCl4 promoters. TMSOF and silyloxydienes, resulting from 2,2,6-trimethyl-[1,3]-dioxin-4-one derivatives, required stoichiometric amount of SiCl4, while vinylogous aldol reaction of Chan's and Danishefsky's dienes took satisfactorily place in the presence of catalytic or sub-stoichiometric amount of catalyst.

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).

Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. Part 39. Enantioselective Synthesis of 1,3-Dioxin-4-ones Having 2,3-Dihydroxy- or 2,3,4-Trihydroxyalkyl Groups at the 6-Position: Versatile Building Blocks of Polyhydroxylated 4-7 Carbon Backbones

1,3-Dioxin-4-ones having 3-hydroxyprop-1-enyl and 2-hydroxybut-3-enyl groups at the 6-position afford, after the Sharpless asymmetric epoxidation followed by epoxide ring cleavage, the 6-- and 6-dioxinones.The former acts as a four- and six-carbon building block, while the latter as a five- and seven-carbon building block.