354529-99-0

Upstream product

• 942-92-7 caprophenone 
• 100-97-0 hexamethylenetetramine 
• 50-00-0 formaldehyd 
• 100-52-7 benzaldehyde 
• 693-02-7 hex-1-yne 
• 91962-95-7 α-acetoxymethyl phenyl vinyl ketone 
• 2234-82-4 1-propylmagnesium chloride 
• 15121-79-6 2-(hydroxymethyl)-1-phenylprop-2-en-1-one 
• 1129-65-3 (hex-1-yn-1-yl)benzene 
• 41531-80-0 2-hydroxymethyl-1-phenyl-1-hexanone 
• 124-38-9 carbon dioxide 
• 84370-13-8 (1-phenyl-2-(triphenyl-λ5-phosphanylidene)hexan-1-one) 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1396011-20-3 (R)-2-((benzylthio)methyl)-1-phenylhexan-1-one 
• 76937-26-3 2-butyl-2,3-dihydro-1H-inden-1-one 

Relevant academic research and scientific papers

Synthesis method of terminal olefin type compound

The invention discloses a synthesis method of a terminal olefin type compound. The synthesis method comprises the following steps: taking a phosphorus ylide compound as a raw material and carbon dioxide as a C1 synthon in an organic solvent; reacting in the presence of a reducing agent to prepare the terminal olefin type compound, wherein the mole ratio of the phosphorus ylide compound to the reducing agent is 1 to (1 to 6) and the pressure of carbon dioxide is 1 to 3atm. The synthesis method disclosed by the invention has the advantages of convenience for operation, moderate conditions, widesubstrate applicable range and high efficiency; the defects in the prior art are filled; the synthesis method takes the carbon dioxide as synthon and carbon dioxide can be effectively absorbed so thata greenhouse effect is effectively prevented.

Transition-Metal-Free Reductive Deoxygenative Olefination with CO2

A new transition-metal-free reductive deoxygenative olefination of phosphorus ylides with CO2, an abundant and sustainable C1 chemical feedstock, is described. This catalytic CO2 fixation afforded β-unsubstituted acrylates and vinyl ketones in good yields with broad scope and good functional group tolerance under mild reaction conditions. Cost-effective and easily handled polymethylhydrosiloxane was used as a reductant. Bis(silyl)acetal was proved to be the key intermediate in this reductive functionalization of CO2.

Thermal retro-aldol reaction using fluorous ether F-626 as a reaction medium

A high-boiling, fluorous-organic hybrid ether, F-626, was tested for use in thermal retro-aldol reactions and found to be an excellent reaction medium in view of the ease of separation from the product by fluorous/organic biphasic treatment. The recovered F-626 can be readily reused for subsequent runs.

The cation exchange resin-promoted coupling of alkynes with aldehydes: one-pot synthesis of α,β-unsaturated ketones

Alkynes undergo smooth coupling with aldehydes in the presence of Amberlyst-15 at room temperature to produce the corresponding α,β-unsaturated ketones in high yields with E-geometry. The use of an inexpensive, readily available, and recyclable cation exchange resin makes this method quite simple and convenient.

A direct synthesis of α-(hydroxymethyl) and α-alkyl-vinyl alkyl ketones

Reaction of 2,4-diketoesters 3a-c with aqueous formaldehyde using potassium carbonate solution as base affords the corresponding α-methylene-β-hydroxyalkanones 4a-c which provide a route to α,β-unsaturated alkyl ketones 6a-e via coupling of α-acetoxymethy

Synthesis and stereochemical aspects of 2,6-disubstituted perhydroazulenes - Core units for a new class of liquid crystalline materials

A novel approach for the synthesis of cis/trans-fused perhydroazulenes 13-19 is reported. The stereochemistry of the derivatives of carbene addition products 9a-c/20-22, of the 2,6-disubstituted perhydroazulenes 12a-c/23-25, and that of compounds 26-27 has been studied by single-crystal X-ray crystallography. The hydrogenation of the tropylidene to the perhydroazulene skeleton under various conditions is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Preparation of α-methylene ketones by direct methylene transfer

Four methods for the preparation of α-methylene ketones by direct methylene transfer are presented. The procedures were optimized in order to obtain high yields.

Efficient and selective hydroacylation of 1-alkynes with aldehydes by a chelation-assisted catalytic system

Terminal alkynes successfully undergo chelation-assisted hydroacylation with aldehydes to give branched or linear alkyl α,β-unsaturated ketones (see scheme).

Baker's yeast reduction of α-methyleneketones

The bioreduction of α-methyleneketones, R1C(=O)C(=CH2)R2 (R1 = Me, Et, Pr, iso-Bu, Ph, CH2CH2Ph; R2 = Cl, Me, Et, n-Pr, iso-Pr, n-Bu, n-C6H13, Ph, CH2Ph), was mediated by baker's yeast (Saccharomyces cerevisiae) to obtain the corresponding α-methylketones. The R1 and R2 groups had a significant influence on the rate and enantioselectivity of the reductions. The rate of C=C bond reduction was higher than that of C=O bond reduction. Only α-methyleneketones having R1 = Me yielded α-methylketones in high enantioselectivity with e.e.s of 88-99%.

Preparation of acrylophenones and 2-alkyl indanones utilizing hexamethylenetetramine as an inexpensive Mannich reagent

Hexamethylenetetramine/acetic anhydride-promoted α-methylenation of aryl alkyl ketones followed by acid-catalyzed cyclization of the resulting acrylophenones produce 2-alkyl indanones in excellent yields.