7403-42-1

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 3938, 1984 DOI: 10.1021/jo00195a010

InChI:InChI=1/C12H16O/c1-10(13)9-12(2,3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3

Upstream product

• 141-79-7 4-methyl-pent-3-en-2-one 
• 71-43-2 benzene 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 7446-70-0 aluminium trichloride 
• 780-69-8 triethoxyphenylsilane 
• 98-80-6 phenylboronic acid 
• 591-51-5 phenyllithium 
• 64723-72-4 N-Isopropyl-4-methyl-3-penten-2-imin 
• 25080-84-6 3-Methyl-3-phenylbutansaeure-methylester 
• 5340-85-2 2,4-dimethyl-4-phenyl-2-pentanol 
• 64-19-7 acetic acid 
• 100-58-3 phenylmagnesium bromide 
• 603-36-1 triphenylantimony 
• 143-66-8 sodium tetraphenyl borate 

Downstream Products

• 1010-48-6 3-methyl-3-phenylbutanoic acid 
• 1985-57-5 2-methyl-2-phenylpentane 
• 2035-93-0 4-methyl-4-phenyl-pentan-2-ol 
• 911689-29-7 3,5-dimethyl-5-phenylhex-1-yn-3-ol 
• 35699-56-0 2,4-Dimethyl-4-phenyl-2-phenylazo-pentanenitrile 
• 79541-45-0 2-Amino-2,4-dimethyl-4-phenyl-pentanenitrile 
• 856947-98-3 5-methyl-3-oxo-5-phenyl-hexanal 
• 66291-95-0 2-methyl-2-phenyl-4-p-tolyl-pentane 
• 4359-29-9 2-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2-phenyl-propane 
• 5340-85-2 2,4-dimethyl-4-phenyl-2-pentanol 
• 61455-11-6 Bis-(1,1,3-trimethyl-3-phenyl-butyl)-diazene 
• 61455-14-9 N-(1,1,3-trimethyl-3-phenylbutyl)formamide 
• 61455-15-0 1,1,3-trimethyl-3-phenylbutylamine 
• 33603-38-2 ((Z)-1,1-dimethyl-but-2-enyl)benzene 

Relevant academic research and scientific papers

MOF-253-Pd(OAc)2: A recyclable MOF for transition-metal catalysis in water

We report palladium(ii)-functionalized MOF-253 (MOF-253-Pd(OAc)2) as a recyclable catalyst to form all-carbon quaternary centers via conjugate additions of arylboronic acids to β,β-disubstituted enones in aqueous media. We demonstrate MOF-253-Pd(OAc)2 can be reused 8 times to form ketone products in yields above 75% while maintaining its crystallinity. Additions of a range of stereoelectronically diverse arylboronic acids to a variety of β,β-disubstituted enones catalyzed by MOF-253-Pd(OAc)2 occur in modest-to-high yields (34-95%).

Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho-Substituted Benzylic Quaternary Centers

Palladium-catalyzed conjugate addition of arylboronic acids to β,β-disubstituted enones in aqueous media is reported. Additions of a wide range of arylboronic acids to β,β-disubstituted enones occur to form ketone products bearing benzylic all-carbon quaternary centers. These reactions are promoted by a simple catalyst prepared from palladium trifluoracetate and 2,2′-bipyridine. The use of aqueous sodium trifluoracetate as the reaction medium significantly enhances reactivity and enables the formation of challenging bis-benzylic and ortho-substituted benzylic all-carbon quaternary centers.

Cationic Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to β,β-disubstituted enones: Construction of quaternary carbon centers

Cationic Pd(II)-catalyzed addition of arylboronic acids to β,β-disubstituted enones in high yields was developed. This method provided an efficient method for the construction of quaternary carbon centers, and only 0.5 mol % of Pd(II) catalyst was needed.

Disubstituted chalcone oximes as selective agonists of RAR retinoid receptors

Compounds of the formula where the variables are as defined in the specification, are useful for preventing or treating emphysema and related pulmonary conditions of mammals and other diseases and conditions which are responsive to RARγ agonist retinoids, such as skin related diseases, including but not limited to acne and psoriasis.

Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes

The addition of aryltrialkoxysilanes to α,β-unsaturated carbonyl compounds (ketones, aldehydes) and nitroalkenes in the presence of SbCl3, TBAF, AcOH, and a catalytic amount of Pd(OAc)2, in CH3CN at 60 °C, provides the corresponding conjugate addition products in moderate to good yields. The addition of equimolar amounts of SbCl3 and TBAF is necessary for this reaction to proceed smoothly. The arylpalladium complex, which is generated by the transmetalation from a putative hypercoordinate silicon compound, is considered to be the catalytically active species.

Nickel Catalysed 1,4-Addition of Aryl Groups to Enones Using Aryldialkylaluminium Compounds

The transmetallation of arylmagnesium halides or aryllithium with Me2AlCl results in the formation of aryldimethylaluminium compounds.These arylaluminium compounds are useful reagents for conjugate additions to enones in the presence of Ni(acac)2 as a catalyst. 3-Aryl ketones are obtained in good yields in these catalytic reactions.Starting from the 3-oxo-Δ1,4-steroids this method gives access to 1α-arylsteroids. - Keywords: conjugate addition; enones; steroids

Palladium(II)-Catalyzed Conjugate Addition of Aromatics to α,β-Unsaturated Ketones and Aldehydes with Arylantimony Compounds

Triarylstibines react with α,β-unsaturated ketones and aldehydes in acetic acid at room temperature in the presence of AgOAc and a catalytic amount of Pd(OAc)2 to afford the conjugate addition products (the formal hydroarylated compounds to an olefinic part) in good yields. In contrast, diarylantimony chlorides, arylantimony dichlorides, and diphenylantimony acetate react with the enones and enals even in the absence of AgOAc to afford the same products in higher yields compared with those from triarylstibines. These are new C-C bond-forming reactions using arylantimony(III) compounds in which the formation of a palladium enolate or a trivalent antimony enolate is proposed as an intermediate.

Aminocarbonyl (thiocarbonyl) and cyanoguanidine derivatives of quinoline and indoline

Novel compounds having potassium channel activating activity and useful, for example, as antiischemic agents are disclosed. These compounds have the general formula STR1 wherein A is STR2 or a single bond to complete an indoline nucleus; X is --O--, --S-- or --NCN; and the R groups are as defined herein.

Indane and quinoline derivatives

Novel indane and quinoline derivatives, useful, for example, as antiischemic agents, having the formula STR1 where A, X, R1 -R7 are as defined herein, are disclosed.

A New Catalytic Activity of Antimony(III) Chloride in Palladium(0)-Catalyzed Conjugate Addition of Aromatics to α,β-Unsaturated Ketones and Aldehydes with Sodium Tetraphenylborate and Arylboronic Acids

A remarkable catalytic effect of antimony(III) chloride is disclosed in palladium(0)-catalyzed conjugate addition of aromatics to α,β-unsaturated ketones and aldehydes with sodium tetraphenylborate and arylboronic acids in acetic acid at 25 deg C.Several other metal chlorides such as AlCl3, SnCl4, AsCl3, TiCl4, FeCl3, MoCl5, and CeCl3 are also effective in some cases, but SbCl3 is the salt of choice.Two key steps are proposed for this reaction: one is the oxidative addition of a C-B bond to Pd(0) forming an arylpalladium species, and the other is the formation of an antimony enolate derived from the initial coordination of SbCl3 to the carbonyl oxygen of an organopalladium intermediate.