85157-92-2

Usage

InChI:InChI=1/C13H18O2/c1-13(2,3)9-12(14)10-5-7-11(15-4)8-6-10/h5-8H,9H2,1-4H3

Upstream product

• 66582-09-0 1-(3,3-dimethylbut-1-yn-1-yl)-4-methoxybenzene 
• 507-19-7 t-butyl bromide 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 79958-53-5 (E)-1-(3,3-dimethylbut-1-en-1-yl)-4-methoxybenzene 
• 917-54-4 methyllithium 
• 33868-76-7 1-(4-methoxyphenyl)-3,3-bis(methylsulfanyl)propenone 
• 74-88-4 methyl iodide 
• 1070-83-3 tert-Butylacetic acid 
• 7065-46-5 3,3-dimethylbutanoic acid chloride 
• 100-66-3 methoxybenzene 
• 1283231-70-8 (E)-2-(1-(4-methoxyphenyl)-3,3-dimethylbut-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 719311-17-8 2-bromo-3,3-dimethyl-1-(4-triisopropylsilanyloxy-phenyl)-butan-1-one 
• 719310-88-0 3,3-dimethyl-1-(4-triisopropylsilanyloxy-phenyl)-butan-1-one 
• 503445-05-4 2-(2,5-dihydroxy-phenylsulfanyl)-3,3-dimethyl-1-(4-triisopropylsilanyloxy-phenyl)-butan-1-one 
• 14392-74-6 1-(4-Hydroxy-phenyl)-3,3-dimethyl-butan-1-one 

Relevant academic research and scientific papers

Preparation method of aryl ketone compound

The invention provides a preparation method of an aryl ketone compound, and belongs to the technical field of compound synthesis. The method comprises the following steps: under the action of a silver catalyst and water, carrying out reaction on aryl alkyne with a structure as shown in a formula 1 in a solvent at 60-120 DEG C for 12-48 hours, and separating and purifying a product after the reaction is finished, so as to obtain the single aryl ketone compound with a structure as shown in a formula I, the raw materials are easy to obtain, the experimental operation is simple, the yield of the prepared single aryl ketone compound is good, and gram-scale experiments can be carried out.

Ring size and nothing else matters: unusual regioselectivity of alkyne hydration by NHC gold(i) complexes

We have investigated the role of ring sizes and substituents in NHC ligands in some (NHC)Au(i) complexes in the hydration of internal alkynes. Despite the fact that using (NHC)Au(i) complexes in the hydration of diarylacetylenes leads to Markovnikov-type products, the precise tuning of ligands allows changing the regioselectivity in arylalkylacetylene hydration to the anti-Markovnikov-type.

Palladium-Catalyzed Dual Ligand-Enabled Alkylation of Silyl Enol Ether and Enamide under Irradiation: Scope, Mechanism, and Theoretical Elucidation of Hybrid Alkyl Pd(I)-Radical Species

We report herein that a palladium catalyst in combination with a dual phosphine ligand system catalyzes alkylation of silyl enol ether and enamide with a broad scope of tertiary, secondary, and primary alkyl bromides under mild irradiation conditions by blue light-emitting diodes. The reactions effectively deliver α-alkylated ketones and α-alkylated N-acyl ketimines, and it is difficult to prepare the latter by other methods in a stereoselective manner. The α-alkylated N-acyl ketimine products can be further subjected to chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester to deliver chiral N-acyl-protected α-arylated aliphatic amines in high enantioselectivity up to 99% ee, thus providing a method for facile synthesis of chiral α-arylated aliphatic amines, which are of importance in medicinal chemistry research. The N-acetyl ketimine product also reacted smoothly with various types of Grignard reagents to afford sterically bulky N-acetyl α-tertiary amines in high yields. Theoretical studies in combination with experimental investigation provide understanding of the reaction mechanism with respect to the dual ligand effect and the irradiation effect in the catalytic cycle. The reaction is suggested to proceed via a hybrid alkyl Pd(I)-radical species generated by inner-sphere electron transfer of phosphine-coordinated Pd(0) species with alkyl bromide. This intriguing hybrid alkyl Pd(I)-radical species is elucidated by theoretical calculation to be a triplet species coordinated by three phosphine atoms with a distorted tetrahedral geometry, and spin prohibition rather than metal-to-ligand charge transfer contributes to the kinetic stability of the hybrid alkyl Pd(I)-radical species to impede alkyl recombination to generate Pd(II) alkyl intermediate.

Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives

We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.

Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes

The copper-catalyzed addition of bis(pinacolato)diboron to internal alkynes in the presence of methanol generates alkenylboron compounds with high levels of regio- and stereoselectivities. The catalytic efficiency is increased by using monodentate phosphine ligands, especially P(p-tolyl)3 and a range of internal alkynes was borylated in good yields. The Royal Society of Chemistry.

Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation

The allylic hydrogen is found to have a dramatic effect on the regioselectivity of the Wacker oxidation, leading to the postulation that an agostic hydrogen or enyl (σ + π) complex helps to stabilise the key intermediate.

Vinylcations, 39. Zinc Chloride Catalysed Addition of Hydrogen Chloride to Cyclopropylalkynes

Zinc chloride catalysed addition of hydrogen chloride to 1-cyclopropylalkynes 5a-e (R = CH3, c-C3H5, phenyl, p-tolyl, 4-methoxyphenyl) is studied and the results are compared with those of the addition of HCl/ZnCl2 to several substituted arylalkynes 10a-h.Thus, the alkynes are reacted with HCl/ZnCl2 in dichloromethane and the reaction products are investigated also with respect to their stereochemistry.All alkynes yield predominantly the direkt hydrogen chloride addition products.The 1-cyclopropylalkynes 5a-d give (E)-1-chloro-1-cyclopropyl-1-alkenes 15, and (E)-1-chloro-2-cyclopropyl-1-(4-methoxyphenyl)ethene (16e) is obtained as the major product from 5e (R = 4-CH3OC6H4).Moreover, ring opening to homoallenyl chlorides 19 and, as a side reaction, formation of the ketones 17 and 18 by the addition of water are observed.In a secondary addition reaction, the dichlorides 20 are also obtained by homoallyl rearrangement.The arylalkynes 10a-g react preferentially with formation of (E)-1-aryl-1-chloroalkenes 21.Relative rates are obtained by inter- and intramolecular competition reactions of the alkynes 23 and 5b-e with HCl/ZnCl2 showing the order of stabilization by substituents of the intermediate vinyl cation 2 to be 4-ClC6H4 E2 mechanism.The preferential formation of the addition products E-15, E-16, and E-21 is attributed to a syn-vinyl cation ion pair and to steric approach control of the β-substituents in the vinyl cation intermediate 2.

Mechanism of Nucleophilic Addition to the Carbonyl Group. Part III. Evidence for the Reactant-like Nature of the Transition State in the LiAlH4 Reduction of Alkyl Aryl Ketones.

A Hammett-type free energy relationship is established for the LiAlH4 reduction of 1-(X-phenyl)-2,3,3-trimethyl-1-butanones (X = H, p-F, m-F, p-Me, m-Me, p-MeO, m-MeO, p-NMe2 and m-NMe2) in Et2O at 30 deg C.A ρ value of 1.77 has been obtained.Rate ratios