29568-66-9Relevant academic research and scientific papers
Practical synthesis of functionalized terminal alkynes, 3,3,3-triethoxypropyne and ketal protected prop-2-ynones
Karanfil, Abdullah,Eskici, Mustafa
, p. 2342 - 2351 (2017/12/12)
Practical and economical synthesis of synthetically valuable 3,3,3-triethoxypropyne, ketal protected phenyl and methyl substituents prop-2-ynones is described. Bromination and subsequent 18-crown-6 catalyzed elimination of triethylorthoacrylate and ketal
Method for synthesizing alpha-alkenylketal
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Paragraph 0029, (2016/11/17)
The invention discloses a method for synthesizing alpha-alkenylketal. The method comprises the following steps: carrying out reaction on propynol and ethylene glycol under the actions of a catalyst, a solvent and the like, and carrying out separation and purification to obtain the alpha-alkenylketal. In the alpha-alkenylketal, the ketocarbonyl group is protected, the alkenyl of the product still has very high reaction activity and can be subjected to a series of reactions (addition, oxidation, polymerization and the like), and acidification is carried out after the reactions to obtain the carboxylic compound, thereby preventing the carbonyl from changing due to the influence in the reaction process. The method adopts a one-pot reaction process, avoids the process of preparing the alpha-alkenylcarbonyl compound before the synthesis of the carbonyl compound from propynol, is simple to operate, and has the advantages of low energy consumption, simple after-treatment and green and environment-friendly technique.
An expedient, flexible and convergent access to selectively protected 1,5-dicarbonyl compounds. Applications to the synthesis of 2,6-disubstituted pyridines and thiopyridines
Boivin, Jean,Carpentier, Floriane,Jrad, Rafik
, p. 1664 - 1672 (2007/10/03)
Intermolecular addition of 2-oxoalkyl radicals generated from the corresponding S-alkyl-O-ethyl dithiocarbonates on vinyl ketals afforded selectively protected 1,5-dicarbonyl compounds in good yields. These key-intermediates can be converted into a plethora of useful substances. Transformations to pyridines and thiopyridines were given as examples. Georg Thieme Verlag Stuttgart.
Synthetic 6-aryl-2-hydroxy-6-ketohexa-2,4-dienoic acid substrates for C-C hydrolase BphD: Investigation of a general base catalytic mechanism
Speare, Damian M.,Fleming, Sarah M.,Beckett, Martin N.,Li, Jian-Jun,Bugg, Timothy D. H.
, p. 2942 - 2950 (2007/10/03)
A chemical synthesis of the 2-hydroxy-6-ketohexa-2,4-dienoic acid intermediates on bacterial meta-cleavage pathways has been established, using a Heck coupling strategy. Coupling of ethyl 3-bromo-2-acetoxyacrylate with 1-aryl vinyl ketals or 1-aryl allylic alcohols proceeded in 70-90% yield. Heck coupling with an alkyl vinyl ketal was also successful, allowing the synthesis of an alkyl-substituted ring fission intermediate. The synthetic ring fission intermediates were used to investigate the enzymatic reaction catalysed by C-C hydrolase BphD from Pseudomonas LB400. A reduced substrate analogue 2,6-dihydroxy-6-phenylhexa-2,4-dienoic acid was processed enzymatically to benzaldehyde by C-C hydrolase BphD, consistent with a catalytic mechanism involving general base-catalysed attack of water to give a gem-diol intermediate, and not consistent with a nucleophilic mechanism. A series of para-substituted 2-hydroxy-6-keto-6-phenylhexa-2,4-dienoic acid substrates were assayed against BphD, and the derived Hammett plot (ρ = -0.71) is consistent with a departing carbanion in the transition state for C-C cleavage.
A convenient synthesis of 2-aryl-2-vinyl-[1,3]-dioxolanes and -dioxanes
Gutzmann,Messinger
, p. 523 - 525 (2007/10/02)
Cyclocondensation of γ-aryl-γ-oxosulfones 1 with 1,2- or 1,3-dioles 2 and 3 leads to 2-aryl-2-sulfonylethyl-[1,3]-dioxolanes 4 and -dioxanes 5, respectively. In the presence of potassium tert-butoxid 4 and 5 eliminate sulfinic acid yielding the title comp
Application of Oxidative Aryl Migration in Organo-selenium and -tellurium Compounds to the Synthesis of 2-Arylpropanoic Acids
Uemura, Sakae,Fukuzawa, Shin-ichi,Yamauchi, Takayoshi,Hattori, Kaneaki,Mizutaki, Shoichi,Tamaki, Kentaro
, p. 1983 - 1987 (2007/10/02)
The ethylene acetals of aryl α-phenylseleno- and α-phenyltelluro-ethyl ketones i, Ph, Br) and 5-bromo-6-methoxy-2-naphthyl> have been prepared in 12-83percent yields by treating the corresponding α-bromo compounds with diphenyl diselenide-sodium or diphenyl ditelluride-sodium, respectively, in tetrahydrofuran-dimethylformamide under reflux for 6-10 h, during which the bromine is substituted by the PhSe or PhTe group.This substitution is not observed when the (PhM)2-NaBH4-EtOH (M=Se, Te) system which is known as a source of PhM- anion is used.Oxidation of the acetals thus formed with an excess of meta-chloroperbenzoic acid at 20-25 deg C for 1 h affords hydroxy-ethyl 2-arylpropanoates in 56-86percent yields via aryl group migration which are hydrolysed to 2-arylpropanoic acids, some of which are pharmaceutically important compounds.Overall isolated yields of 2-arylpropanoic acids are around 30-42percent based on the starting propiophenones over 5 steps.
