33553-82-1

Upstream product

• 126404-88-4 tert-Butyl-carbamic acid 4-chloro-1-phenyl-butyl ester 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 22815-63-0 N-^t-butyl benzylcarbamate 
• 71-43-2 benzene 
• 935-64-8 1-phenyl-1-cyclobutanol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 65488-06-4 (S)-4-chloro-1-phenyl-1-butanol 
• 2060-65-3 2-phenyl tetrahydro thiophene 
• 160550-43-6 Acetic acid 4-chloro-1-phenyl-butyl ester 
• 7515-46-0 (E)-(4-chlorobut-1-en-1-yl)benzene 
• 215391-93-8 2-[Benzyl-(4-hydroxy-4-phenyl-butyl)-amino]-1-phenyl-ethanone 
• 87372-61-0 2-phenyl-2-allyltetrahydrofuran 
• 1469994-83-9 trimethyl(2-phenyltetrahydrofuran-2-yl)silane 
• 1469994-84-0 2-phenyl-2-(tributylstannyl)tetrahydrofuran 
• 1469994-85-1 2-phenyl-2-(phenylthio)tetrahydrofuran 
• 1469994-88-4 2-(2-phenyltetrahydrofuran-2-yl)propan-2-ol 
• 1469994-91-9 2-phenyltetrahydrofuran-2-carbaldehyde 
• 1469994-92-0 diphenyl(2-phenyltetrahydrofuran-2-yl)phosphine 
• 60507-03-1 acetophenone-d1 
• 1469994-82-8 2-deuterio-2-phenyltetrahydrofuran 

Relevant academic research and scientific papers

Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds

The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.

Interrupting the Barton?McCombie reaction: Aqueous deoxygenative trifluoromethylation of o-alkyl thiocarbonates

The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of O-alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.

Copper-Catalyzed N?F Bond Activation for Uniform Intramolecular C?H Amination Yielding Pyrrolidines and Piperidines

The dual function of the N?F bond as an effective oxidant and subsequent nitrogen source in intramolecular aliphatic C?H functionalization reactions is explored. Copper catalysis is demonstrated to exercise full regio- and chemoselectivity control, which

Effect of functional groups in organic chlorides on radical reduction with hydrostannane under microwave irradiation

The effect of functional groups on the activation of molecules by microwave irradiation in the reduction of organic chlorides by Bu3SnH was investigated. The reactivity of a substrate with a hydroxy group increased under microwave heating conditions in comparison with conventional heating.

Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols

A novel and regioselective approach to carbonyl-containing alkyl chlorides via silver-catalyzed ring-opening chlorination of cycloalkanols is reported. Concurrent C(sp3)-C(sp3) bond cleavage and C(sp3)-Cl bond formation efficiently occur with good yields under mild conditions, and the chlorinated products are readily transformed into other useful synthetic intermediates and drugs. The reaction features complete regioselectivity, high efficiency, and excellent practicality. (Chemical Equation Presented).

A combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations

The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using experimental and computational methods to gain deeper insight into trends in reactivity.

Gated access to α-lithiated phenyltetrahydrofuran: Functionalisation via direct lithiation of the parent oxygen heterocycle

Cycloreversion of α-lithiated phenyltetrahydrofuran was successfully tamed at -78 °C in a non-coordinating solvent in the presence of TMEDA. This anion showed excellent nucleophilicity and could be intercepted with a variety of structurally different electrophiles to give 2,2-disubstituted derivatives which can be further elaborated to γ-butyrolactones. The Royal Society of Chemistry 2013.

Synthesis and pharmacological characterization of novel inverse agonists acting on the viral-encoded chemokine receptor US28

G-protein coupled receptors encoded by viruses represent an unexplored class of potential drug targets. In this study, we describe the synthesis and pharmacological characterization of the first class of inverse agonists acting on the HCMV-encoded receptor US28. It is shown that replacement of the 4-hydroxy group of lead compound 1 with a methylamine group results in a significant 6-fold increase in affinity. Interestingly, increasing the rigidity of the spacer by the introduction of a double bond also leads to a significant increase in binding affinity compared to 1. These novel inverse agonists serve as valuable tools to elucidate the role of constitutive signaling in the pathogenesis of viral infection and may have therapeutic potential as leads for new antiviral drugs.

Synthesis and structure-activity relationship of the first nonpeptidergic inverse agonists for the human cytomegalovirus encoded chemokine receptor US28

US28 is a human cytomegalovirus (HCMV) encoded G-protein-coupled receptor that signals in a constitutively active manner. Recently, we identified 1 {5-(4-(4-chlorophenyl)-4-hydroxy-piperidin-1-yl)-2,2-diphenylpentanenitrile} as the first reported nonpeptidergic inverse agonist for a viral-encoded chemokine receptor. Interestingly, this compound is able to partially inhibit the viral entry of HIV-1. In this study we describe the synthesis of 1 and several of its analogues and unique structure-activity relationships for this first class of small-molecule ligands for the chemokine receptor US28. Moreover, the compounds have been pharmacologically characterized as inverse agonists on US28. By modification of lead structure 1, it is shown that a 4-phenylpiperidine moiety is essential for affinity and activity. Other structural features of 1 are shown to be of less importance. These compounds define the first SAR of ligands on a viral GPCR (US28) and may therefore serve as important tools to investigate the significance of US28-mediated constitutive activity during viral infection.

Novel phenylheteroalkylamine derivatives

There are provided novel compounds of formula (I), wherein R1, R2, X, Y, V, W and Z are as defined in the specification, and pharmaceutically acceptable salts thereof, and enantiomers and racemates thereof; together with processes for their preparation, compositions containing them and their use in therapy. The compounds are inhibitors of nitric oxide synthase and are thereby particularly useful in the treatment or prophylaxis of inflammatory disease and pain.