20047-50-1Relevant academic research and scientific papers
A Convenient Method for Preparing Aromatic α,β-Unsaturated Ketones from α,β-Unsaturated Acyl Chlorides and Arylboronic Acids via Suzuki-Miyaura Type Coupling Reaction
Urawa, Yoshio,Nishiura, Katsutoshi,Souda, Shigeru,Ogura, Katsuyuki
, p. 2882 - 2885 (2003)
Aromatic α,β-unsaturated ketones are synthesized efficiently by palladium-catalyzed cross-coupling reaction of arylboronic acids with α,β-unsaturated acyl chlorides in the presence of K 3PO4 hydrate in toluene.
Borane-Catalyzed Direct Asymmetric Vinylogous Mannich Reactions of Acyclic α,β-Unsaturated Ketones
Tian, Jun-Jie,Liu, Ning,Liu, Qi-Fei,Sun, Wei,Wang, Xiao-Chen
supporting information, p. 3054 - 3059 (2021/03/01)
Herein, we report that, by using chiral bicyclic bisborane catalysts, we have achieved the first highly regio-, diastereo-, and enantioselective direct asymmetric vinylogous Mannich reactions of acyclic α,β-unsaturated ketones. The strong Lewis acidity and steric bulk of the bisborane catalysts were essential for the observed high yields and selectivities.
PROTEIN CROSSLINKING INHIBITOR AND USE OF THE SAME
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Page/Page column 29, (2012/11/08)
The present invention relates to: a ketone compound having transglutaminase-inhibiting activity, which is represented by the following Formula 1, 2, or 3: wherein R1 is a substituted or unsubstituted aryl or heterocyclyl group, R2, R3, and R4 are hydrogen atoms, n is 2, X is halogen, R5 and R6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R5 and R6 are not hydrogen atoms at the same time, or R5 and R6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N); an inhibitor of protein crosslinking comprising the compound; and a composition for preventing or treating a protein-crosslinking causative disease, which comprises the compound or the protein crosslinking inhibitor.
Iridium-Catalyzed coupling reaction of primary alcohols with 2-alkynes leading to hydroacylation products
Hatanaka, Shintaro,Obora, Yasushi,Ishii, Yasutaka
experimental part, p. 1883 - 1888 (2010/06/20)
A novel iridium-catalyzed intermolecular coupling reaction of primary alcohols or aldehydes with 2-alkynes was successfully achieved with high regioselectivity to give hydroacylation products such as α,β- unsaturated ketones in good yields. The mechanistic investigation of the reaction strongly indicated that the coupling proceeds through the initial formation of homoallylic alcohols followed by dehydrogenation to β,γ-unsatutated ketones and then isomerisation, which leads to the hydroacylation products.
Hydroacylation of 2-butyne from the alcohol or aldehyde oxidation level via ruthenium catalyzed C-C bond forming transfer hydrogenation
Williams, Vanessa M.,Leung, Joyce C.,Patman, Ryan L.,Krische, Michael J.
supporting information; experimental part, p. 5024 - 5029 (2009/10/24)
Under the conditions of ruthenium catalyzed transfer hydrogenation, 2-butyne couples to alcohols 1a-1j to deliver α,β-unsaturated ketones 3a-3j in good to excellent isolated yields with complete E-stereoselectivity. Under identical conditions, aldehydes 2
Nickeladihydrofuran. Key intermediate for nickel-catalyzed reaction of alkyne and aldehyde
Ogoshi, Sensuke,Arai, Tomoya,Ohashi, Masato,Kurosawa, Hideo
, p. 1347 - 1349 (2008/12/21)
The formation of a nickeladihydrofuran by oxidative cyclization of an alkyne and an aldehyde with nickel(0) has been demonstrated; the transformation of the nickeladihydrofuran into an enone by decomposition, a lactone by carbonylation and an allylic alcohol by treatment with ZnMe2 suggests that nickeladihydrofuran is an important key intermediate in a variety of catalytic reactions. The Royal Society of Chemistry.
Difluoro-λ3-bromane-induced oxidative carbon-carbon bond-forming reactions: Ethanol as an electrophilic partner and alkynes as nucleophiles
Ochiai, Masahito,Yoshimura, Akira,Mori, Takeshi,Nishi, Yoshio,Hirobe, Masaya
, p. 3742 - 3743 (2008/09/21)
Reported here for the first time are the oxidative couplings of alkynes and primary alcohols yielding conjugated enones. Although the BF3-catalyzed reaction of terminal alkynes with p-trifluoromethylphenyl(difluoro)-λ3-bromane results in the fluoro-λ3-bromanation of triple bonds to afford (E)-β-fluorovinyl-λ3-bromanes, reaction of an alkyne with the difluoro-λ3-bromane in the presence of an alcohol and BF3-Et2O affords directly conjugated enones in good yields. The reaction proceeds in a highly stereo- and regioselective manner under metal-free conditions. Interestingly, no formation of enones was detected, when difluoro-λ3-iodane p-CF3C6H4IF2 was used instead of the λ3-bromane. A mechanism involving a λ3-bromane-induced oxidation of an alcohol to an aldehyde, [2 + 2] cyclization with alkynes yielding 2H-oxetes, and finally the electrocyclic ring opening is discussed. Copyright
Ruthenium-Catalyzed Allylation of Primary Alcohols by Allylic Acetates: A Novel Synthesis of α,β-Unsaturated Ketones
Kondo, Teruyuki,Mukai, Takeshi,Watanabe, Yoshihisa
, p. 487 - 489 (2007/10/02)
Certain ruthenium complexes show high catalytic activity in the synthesis of α,β-unsaturated ketones from primary alcohols and allylic acetates.Here, ?-allylruthenium intermediates apparently operate as nucleophiles rather than as electrophiles.
Cathodic Addition of Benzylidyne Trichloride to Ketones and Aldehydes
Steiniger, Michael,Schaefer, Hans J.
, p. 125 - 132 (2007/10/02)
Ketones are converted to homologated enones 7a-g in good yields by cathodic addition of benzylidyne trichloride (1d).As intermediates α-Chlorooxiranes 6 are assumed, which rearrange via α-keto carbenium ions 9 to enones.The intermediacy of 9 is supported by the addition of 1d to norcamphor, where the products indicate equilibrating norbornyl cations as intermediates. α,β-Unsaturated ketones lead depending on steric shielding of the double bond to the cyclopropane 23 as 1,4-adduct or the enone 26 as 1,2-adduct.With aldehydes and 1d, α-chloro or βhydroxy ketones, the conversion products of 2-chlorooxiranes, are obtained.
Synthesis of β,γ- and α,β-Unsaturated Ketones Using Allyltitanium Reagents
Reetz, Manfred T.,Wenderoth, Bernd,Urz, Ralf
, p. 348 - 353 (2007/10/02)
Carboxylic acid imidazolides (N-acylimidazoles) (4, 7a-c, 12) react with allyltitanium tris(amides) (3b, c, 10) to form β,γ-unsaturated ketones (5, 8a-c, 11a-d, 13) without carbinol formation or isomerization of the olefinic double bond.Controlled isomerization to α,β-isomers having E-configuration is possible under mild conditions using Al2O3.
