31366-07-1

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 6185, 1980 DOI: 10.1021/ja00539a056

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

Upstream product

• 7065-46-5 3,3-dimethylbutanoic acid chloride 
• 71-43-2 benzene 
• 5650-07-7 3-methyl-1-phenyl-but-2-en-1-one 
• 15681-48-8 lithium dimethylcuprate 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 3677-81-4 diphenylboronchloride 
• 5123-17-1 bromodiphenylborane 
• 4250-82-2 (3,3-dimethyl-but-1-ynyl)benzene 
• 33119-75-4 2-Brom-3,3-dimethyl-1-phenyl-1-butanon 
• 100-52-7 benzaldehyde 
• 38442-51-2 tert-butylmercury chloride 
• 98-86-2 acetophenone 
• 93-89-0 benzoic acid ethyl ester 
• 594-19-4 tert.-butyl lithium 

Downstream Products

• 14392-86-0 phenyl 3,3-dimethylbutyrate 
• 62338-03-8 α-neo-pentylbenzyl alcohol 
• 71491-53-7 2-chloro-3,3-dimethyl-1-phenyl-1-butanone 
• 17314-92-0 (3,3-dimethylbutyl)benzene 
• 89549-37-1 N-pivaloyl benzamide 
• 82894-43-7 β,β-dimethyl-α-oximinobutyrophenone 
• 33119-75-4 2-Brom-3,3-dimethyl-1-phenyl-1-butanon 
• 121435-99-2 Z-2-hydroxyimino-1-phenyl-3,3-dimethylbutan-1-one 
• 81788-82-1 (R,R/S,S)-2-(Bromphenylmethyl)-3,3-dimethyl-1-phenyl-1-butanon 
• 100649-51-2 ββ-di-isopropyl-α-neopentylstyrene 
• 106149-64-8 2,2,9,9-tetramethyl-4,7-diphenyldec-5-yn-4,7-diol 
• 71527-78-1 2,2-Dichloro-3,3-dimethyl-1-phenyl-butan-1-one 
• 77387-76-9 3,3-Dimethyl-1-phenyl-1-thioxo-2-butanon 
• 77387-78-1 3,3-Dimethyl-1-phenyl-2-thioxo-1-butanon 

Relevant academic research and scientific papers

Identification of a novel neuropeptide s receptor antagonist scaffold based on the sha-68 core

Activation of the neuropeptide S receptor (NPSR) system has been shown to produce an-xiolytic-like actions, arousal, and enhance memory consolidation, whereas blockade of the NPSR has been shown to reduce relapse to substances of abuse and duration of anesthetics. We report here the discovery of a novel core scaffold (+) N-benzyl-3-(2-methylpropyl)-1-oxo-3-phenyl-1H,3H,4H,5H,6H,7H-furo[3,4-c]pyridine-5-carboxamide with potent NPSR antagonist activity in vitro. Pharmacokinetic parameters demonstrate that 14b reaches pharmacologically relevant levels in plasma and the brain following intraperitoneal (i.p.) administration, but is cleared rapidly from plasma. Compound 14b was able to block NPS (0.3 nmol)-stimulated locomotor activity in C57/Bl6 mice at 3 mg/kg (i.p.), indicating potent in vivo activity for the structural class. This suggests that 14b can serve as a useful tool for continued mapping of the pharmacological functions of the NPS receptor system.

Method for synthesizing aryl ketone compound by taking AQ as photocatalyst

The invention provides a method for synthesizing an aryl ketone compound by taking AQ as a photocatalyst. The method comprises the following steps that AQ serves as a photocatalyst; under the conditions of a palladium catalyst, a phosphine ligand, weak base and an organic solvent, a 390-to-430-nm photocatalysis lamp is used for irradiation at room temperature in an inert protective atmosphere, soan aldehyde group-containing compound reacts with Ar-X, wherein Ar-X is aryl halide or aryl trifluoromethanesulfonic acid, the aryl halide is aryl bromide or aryl iodide, and the aldehyde group-containing compound is one selected from aryl aldehyde, alkyl aldehyde, linear primary aldehyde and acyclic secondary aldehyde. According to the invention, the anthraquinone (AQ) HAT photocatalyst and palladium catalyst are combined for use, C-H arylation and alkenylation reactions of aldehyde can be directly carried out to synthesize ketone, and reaction efficiency is high. The method has the advantages of mild reaction conditions, high yield and a wide substrate application range, and can be used for synthesizing natural products in medicinal plants.

Direct C-H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis

Herein, we report that merging palladium catalysis with hydrogen atom transfer (HAT) photocatalysis enabled direct arylations and alkenylations of aldehyde C-H bonds, facilitating visible light-catalyzed construction of a variety of ketones. Tetrabutylammonium decatungstate and anthraquinone were found to act as synergistic HAT photocatalysts. Density functional theory calculations suggested a Pd0-PdII-PdIII-PdI-Pd0 pathway and revealed that regeneration of the Pd0 catalyst and the photocatalyst occurs simultaneously in the presence of KHCO3. This regeneration features a low energy barrier, promoting efficient coupling of the palladium catalytic cycle with the photocatalytic cycle. The work reported herein suggests great promise for further applications of HAT photocatalysis in palladium-catalyzed cross-coupling and C-H functionalization reactions to be successful.

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.

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Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations

A new catalytic method is described to access carbocation intermediates via the mesolytic cleavage of alkoxyamine radical cations. In this process, electron transfer between an excited state oxidant and a TEMPO-derived alkoxyamine substrate gives rise to a radical cation with a remarkably weak C?O bond. Spontaneous scission results in the formation of the stable nitroxyl radical TEMPO.as well as a reactive carbocation intermediate that can be intercepted by a wide range of nucleophiles. Notably, this process occurs under neutral conditions and at comparatively mild potentials, enabling catalytic cation generation in the presence of both acid sensitive and easily oxidized nucleophilic partners.

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.

TiCl4-catalyzed indirect anti-Markovnikov hydration of alkynes: Application to the synthesis of benzo[b]furans

(Chemical Equation Presented) An efficient methodology for the indirect anti-Markovnikov hydration of unsymmetrically substituted terminal and internal alkynes is based on TiCl4-catalyzed hydroamination reactions. Its application to ortho-alkynylhaloarenes, followed by a copper-catalyzed O-arylation, provides flexible access to substituted benzo[b]furans.

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The radical alkylation of ketones is achieved by their conversion into corresponding N-silyloxy enamines, followed by a radical reaction with alkyl halides bearing electron-withdrawing groups. The Royal Society of Chemistry 2006.