15831-52-4

Usage

InChI:InChI=1/C13H16O2/c1-15-12-8-6-11(7-9-12)13(14)10-4-2-3-5-10/h6-10H,2-5H2,1H3

Upstream product

• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 100-66-3 methoxybenzene 
• 874-90-8 4-methoxybenzonitrile 
• 33240-34-5 cyclopentylmagnesium bromide 
• 287-92-3 Cyclopentane 
• 201230-82-2 carbon monoxide 
• 877-68-9 4-trimethylsilylanisole 
• 123-11-5 4-methoxy-benzaldehyde 
• 142-29-0 cyclopentene 
• 3400-45-1 cyclopentanecarboxylic acid 
• 20758-61-6 cyclopentyl(4-methoxyphenyl)methanol 
• 100-07-2 4-methoxy-benzoyl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 805240-60-2 6-hydroxy-1-(4-methoxyphenyl)hexan-1-one 

Downstream Products

• 94756-84-0 Bis-(4-methoxy-phenyl)-cyclopentyliden-methan 
• 14151-75-8 Bis-(4-acetoxy-phenyl)-cyclopentyliden-methan 
• 66422-10-4 1,1-bis(4-hydroxyphenyl)methylenecyclopentane 
• 6728-52-5 (1-bromocyclopentyl)(4-methoxyphenyl)methanone 
• 1221406-64-9 1-(1-cyclopentylethyl)-4-methoxybenzene 
• 138644-95-8 4-(1-cyclopentyl-2-phenyl-vinyl)-anisole 

Relevant academic research and scientific papers

Discovery of Novel 3-Amino-4-alkoxyphenylketones as PDE4 Inhibitors with Improved Oral Bioavailability and Safety against Spatial Memory Impairments

To realize PDE4 inhibitors with good developmental potentiality for the treatment of dementia, structure-based optimizations of lead compound FCPR03 resulted in novel aminophenylketones 9c and 9H with low nanomolar potency, which displayed comparable acti

Rapid and Direct Photocatalytic C(sp3)?H Acylation and Arylation in Flow

Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)?C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12–48 hours to only 5–15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process.

1,3-Alkyl Transposition in Allylic Alcohols Enabled by Proton-Coupled Electron Transfer

A method is described for the isomerization of acyclic allylic alcohols into β-functionalized ketones via 1,3-alkyl transposition. This reaction proceeds via light-driven proton-coupled electron transfer (PCET) activation of the O?H bond in the allylic al

Aminophenone compounds as well as preparation method and application thereof

The invention belongs to the technical field of medicinal chemistry, and particularly relates to aminophenone compounds as well as a preparation method and application thereof. The aminophenone compounds provided by the invention have a good inhibition effect on PDE4, also have good bioavailability, can be applied to preparation of drugs for treating PDE4-related diseases, and increase the optionsof drugs for treating PDE4-related diseases; and the effect of a part of the aminophenone compounds is equivalent to the effect of positive drugs, and the aminophenone compounds have good developmentpotential.

Facile preparation of 5-alkyl-1-aryltetrazoles with arenes, acyl chlorides, hydroxylamine, and diphenylphosphoryl azide

Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH?HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.

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.

Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents

Three efficient methods for five-membered ring carbocycle synthesis have been developed from simple starting materials using samarium(II) reagents. A Reformatsky aldol reaction proceeded efficiently with samarium(II) iodide using lithium bromide as an additive. A new intramolecular alkylation of a samarium enolate was realized with a pendant sulfonate ester leaving group. Pinacol cyclization of a simple diketone was also demonstrated giving a diol product in high stereoselectivity. A promising lead result has been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.

Friedel–Crafts reactions of acyl trifluoromethanesulfonates and cyclic acylsulfonium cations generated from acyl fluorides

Reactive acyl trifluoromethanesulfonates are formed from the reaction of acyl fluorides with trimethylsilyl trifluoromethanesulfonate (TMSOTf). These electrophiles undergo Friedel–Crafts reactions with electron-rich aromatics at room temperature. When a sulfur atom is present at their γ position, their cyclization to acylsulfonium cations is observed and is followed by a rearrangement leading to benzothiepinones (or dibenzo[b,e]thiepinones) in 40–85% yield.

Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp3)-H Bond

In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp3)-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.

One-pot Unsymmetrical Ketone Synthesis Employing a Pyrrole-Bearing Formal Carbonyl Dication Linchpin Reagent

A one-pot procedure for the synthesis of unsymmetrical ketones utilizing a pyrrole-bearing carbonyl linchpin reagent (carbonyl linchpin N,O-dimethylhydroxylamine pyrrole; CLAmP) is reported. In contrast to other carbonyl dielectrophile equivalents, CLAmP enables the synthesis of ketones from a variety of organolithium and Grignard reagents. The electrophilic nature of CLAmP enables the addition of less reactive as well as thermally unstable nucleophiles. CLAmP was designed to form kinetically stable tetrahedral intermediates upon the addition of organometallic nucleophiles. Evidence for the existence of persistent tetrahedral intermediates was obtained through in situ IR studies.