70030-51-2

Upstream product

• 88410-17-7 (1-Benzenesulfinyl-3-methyl-buta-1,2-dienyl)-trimethyl-silane 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 5272-33-3 2-methyl-4-(trimethylsilyl)but-3-yn-2-ol 
• 2973-86-6 lithium thiophenoxide 

Downstream Products

• 1553-55-5 DL-3-hydroxy-3-methylglutaryl coenzyme A 
• 546-49-6 artemisia ketone 
• 91587-07-4 4,4-dimethyl-6-<(E)-1-(4-carboxyphenyl)-1-propen-2-yl>-3,4-dihydro-2H-1-benzothiopyran 
• 88579-23-1 3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl methyl ketone 
• 91587-26-7 3-(2-Mercapto-phenyl)-3-methyl-butan-1-ol 
• 88579-35-5 ethyl p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)propenyl] benzoate 

Relevant academic research and scientific papers

Reaction of Ester Enolates with Nucleophiles. Stereocontrolled Formation of Ketone and Aldehyde Enolates

Lithium enolates of carboxylic and thiocarboxylic esters react with nucleophiles to afford ketone and aldehyde enolates and subsequently their enol silyl ethers diastereoselectively.This reaction is applied to the synthesis of γ-damascone, α-damascone, β-safranal, and artemisia ketone.

Conformationally Restricted Retinoids

A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter.These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic acid (1) held in a planar cisoid conformation by inclusion in an aromatic ring.The meta-substituted analogue 3 of 4-benzoic acid (2) was far less active than 2 in both assays.In contrast, the vinyl homologue of 2 (4) and the 7,8-dihydro and 7,8-methano analogues (5 and 6) had activity comparable to that of 2.Analogues of 4-benzoic acid (7) were also screened.Replacement of the tetrahydronaphthalene ring of 7 by a benzonorbornenyl group (9) significantly reduced activity, as did removal of the vinylic methyl group from 9 (10).Replacement of the propenyl group of 9 by a cyclopropane ring (12) also reduced activity.Replacement of the tetrahydronaphthalene ring of 7 by 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran and -benzothiopyran rings (13 and 14) also decreased activity.Inclusion of the 7,9 double bond system of 1 in an aromatic ring (15 and 16) reduced activity, whereas inclusion of the 5,7 double bond system in an aromatic ring enhanced activity (7 and 19).Inclusion of the 11,13 and 9,11,13 double bond systems in aromatic rings (2 and 18) also reduced activity below that of 1.Retinoic acid, 7, 13, 14, and 19 inhibited papilloma tumor formation in mice.Toxicity testing indicated that 7 was more toxic than 1, 13, 14, and 19, 19 was more toxic than 1, and 13 and 14 were less toxic than 1.

NEW TRANSFORMATIONS OF SUBSTITUED ALLENE SULPHOXIDES

The preparation and reactions of trimethylsilyl substituted allene sulphoxides are described.Allenes (2) rearrange on warming to give α,β-unsaturated thiol esters.