6752-80-3

Usage

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 1155, 1978 DOI: 10.1016/S0040-4039(01)94486-7

InChI:InChI=1S/C10H16O/c1-5-9(4)7-10(11)6-8(2)3/h5,7-8H,1,6H2,2-4H3/b9-7-

Upstream product

• 112369-53-6 2,6-dimethylocta-5(E),7-dien-4-ol 
• 41162-17-8 dimethyl 4-methyl-2-oxo-pentyl-1-phosphonate 
• 78-94-4 methyl vinyl ketone 
• 67831-89-4 (Z)-8-Chloro-2,6-dimethyl-oct-6-en-4-one 
• 122124-46-3 (E)-2,6-Dimethyl-oct-5-en-7-yn-4-one 
• 108-64-5 Ethyl isovalerate 
• 122124-47-4 (Z)-2,6-Dimethyl-oct-5-en-7-yn-4-one 
• 136123-55-2 isovaleryl fluorosulfonate 
• 78-79-5 isoprene 
• 5205-07-2 3-methyl-3-buten-1-yl acetate 
• 626-90-4 isovaleraldoxime 
• 122124-45-2 (Z)-2,6-Dimethyl-8-trimethylsilanyl-oct-5-en-7-yn-4-one 
• 122124-43-0 6-Hydroxy-2,6-dimethyl-8-trimethylsilanyl-oct-7-yn-4-one 
• 59417-87-7 4-methyl-2-trimethylsilyloxy-1-pentene 

Relevant academic research and scientific papers

Stereoselective Synthesis of (E)-Tagetone

(E)-Tagetone (8) was prepared in four steps by successive alkylation of 1,3-dithiane (1) by 1-iodo-2-methylpropane (2) and by 3-ethoxy-2-methylacrolein (3), followed by treatment of the intermediate 4 with sulfuric acid.Wittig alkylenation of the resulting aldehyde 5 and removal of the protecting group affords the title compound in good yield. - Key Words: Tagetes glandulifera / (E)-Tagetone / 1,3-Dithiane / Oxopropylenation / Wittig alkylenation

ACYLATION OF 1,3-ALKADIENES BY ACYL FLUOROSULFONATES. STEREOSPECIFIC SYNTHESIS OF E AND Z ISOMERS OF CONJUGATED DIENONES

Acyl fluorosulfonates generated from acyl fluorides and SO3 permits acylation of butadiene and isoprene to give triconjugated dienones.This reaction proceeds stereospecifically and leads to E isomers of the corresponding dienones in the case of butadiene and Z isomers in the case of isoprene.

Reactions with α,β-Unsaturated Nitrile Oxides. Synthetic Studies in the Terpene Field. Synthesis of Tagetones, Ocimenones, Deodarone and Atlantone

The generation and 1,3-dipolar cycloaddition of α,β-unsaturated nitrile oxides are described.Selective reductive cleavage of the isoxazoline ring was achived.Subsequent elimination of water leads to the 1,4-dien-3-one system.The formation of tetrahydro-γ-pyrones is observed.The reactions were applied to the synthesis of tagetones, ocimenones, deodarone and atlantone.

Trityl Salt Catalyzed Aldol Reaction between α,β-Acetylenic Ketones and Silyl Enol Ethers

In the presence of a catalytic amount of trityl salt, α,β-acetylenic ketones react with silyl enol ethers to afford the corresponding aldol adducts (1,2-addition products) stereoselectively in high yields.Naturally occurring monoterpenes, trans- and cis-tagetones, are synthesized by the use of this reaction.

Stereoselective Synthesis of (E)-α-Hydroxy-1,3-dienes via the Reaction of 2,5-Dihydrothiophene S,S-Dioxides with Carbonyl Compounds

A stereoselective synthesis of (E)-α0hydroxy -1,3-dienes, by thermal extrusion from adducts of 2,5-dihydrothiophene S,S-dioxide(1) with aldehydes and ketones, is presented and its extension to the synthesis of the dienone, (E)-tagetone, and of a 1,3,5-triene system, is illustrated.

REACTIONS OF UNSATURATED COMPOUNDS. CXIII. THE STEREOCHEMISTRY AND REGIOCHEMISTRY OF THE ACYLATION OF CONJUGATED SYSTEMS

The stereochemistry and regiochemistry of the low-temperature acylation of vinylacetylene, chloroprene, bromoprene, and isoprene with carboxylic acid chlorides in the presence of aluminum chloride were studied.It was shown that mixtures of the geometric isomers of 3-chloro-1,3-alkadien-5-ones are formed in the case of vinylacetylene, and 1,4-adducts (which undergo stereoselective 1,4-dihydrochlorination with the preferential formation of cis-3-X-1,3-alkadien-5-ones) are formed in the other cases. cis-Tagetone was synthesized with a stereoisomeric purity of 83percent.