88537-43-3

Upstream product

• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 605-65-2 5-(dimethylamino)naphth-1-ylsulfonyl chloride 
• 4124-41-8 p-toluenesulfonylanhydride 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 

Downstream Products

• 705266-30-4 N,N-bis-(3-(4-methoxyphenyl)propyl)-p-toluenesulfonamide 
• 57293-19-3 3-(4-methoxyphenyl)propyl bromide 

Relevant academic research and scientific papers

Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[ b ][1,4]-oxaselenines Formation from Selenocyanates

An expedient preparation of selenium-containing hetero-cycles via an m -chloroperbenzoic acid-mediated seleno-annulation starting from selenocyanate derivatives is described. In spite of its significance, this cyclization reaction is virtually understudied not only from the point of view of its scope, but also from the mechanistic aspects associated to this remarkable transformation. In this sense, several selenocyanate and thiocyanate derivatives bearing an aromatic ring were evaluated as substrates under different reaction conditions of this interesting cyclization yielding important insights on its scope as well as relevant information on the reaction mechanism.

Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents

The development of a copper-catalyzed cross-coupling between primary and secondary (pseudo)halides and bicyclopentyl Grignard reagents is reported. Highly strained bicyclopentanes can be cross-coupled with a large panel of primary alkyl mesylates and secondary alkyl iodides. The catalytic system is simple and cheap, and the reaction is general and chemoselective.

Efficient and mild Ytterbium(III)-catalyzed tosylation of alcohols

Ytterbium(III) trifluoromethanesulfonate efficiently catalyzes the reaction of primary and secondary alcohols with toluenesulfonic acid anhydride to yield the alkyl tosylates in high yields. The reactions were carried out under neutral and mild conditions and product purification was easily achieved by means of short column chromatography.

Synthesis of 11C-labelled bis(phenylalkyl)amines and their in vitro and in vivo binding properties in rodent and monkey brains

Two new 11C-labelled ligands, N-(3-(4-hydroxyphenyl)propyl)-3- (4-methoxyphenyl)propylamine ([11C]2) and N-(3-(4-hydroxyphenyl) butyl)-3-(4-methoxyphenyl)butylamine ([11C]3) were designed based on bis(phenylalkyl)-amines (1) which have been reported as polyamine site antagonists with high-selectivity for NR1A/2B NMDA receptors, and radiolabelling of the corresponding phenol precursors with [11C]methyl iodide was readily accomplished. The in vitro inhibition experiments using rat brain slices showed that [11C]2 and [11C]3 share the binding sites with spermine and/or ifenprodil but not with CP-101,606, a highly potent NR2B-selective NMDA antagonist, and that divalent cations such as Zn 2+ produced significant inhibition of both [11C]2 and [11C]3 bindings. Intravenous injection of [11C]3 in mice showed almost homogenous distribution throughout the brain. Attempts to block the tracer uptake of [11C]3 by pre-injection with the unlabelled 3 or spermine in rats were unsuccessful, but a small decrease in the cerebral uptake of [11C]3 by co-treatment with the unlabelled 3 was observed in a monkey PET study. The present findings indicate that none of these 11C-labelled analogues have potential for PET study of binding sites on the N-methly-D-aspartate (NMDA) receptors.

A real time reaction monitoring using fluorescent dansyl group as a solid-phase leaving group

A real time monitoring method to monitor the progress of the solid-phase reaction has been developed. The substitution reaction on the solid-phase was clearly monitored as a change in the color depth using the fluorescent dansyl group as the leaving group. This methodology is applicable to both parallel and split combinatorial synthesis.

Synthesis of meta,meta-Bridged Biaryls (-Metacyclophanes) via Aryl-Aryl Coupling: Factors affecting the Cyclisation

Two bis(iodoaryl)heptanoids (28) and (33), the iodoarylbutyl iodoarylpropyl sulphide (39), and the corresponding sulphone (40) have been prepared, and each treated with tetrakis(triphenylphosphine)nikel(0).Two new m,m-bridged biaryls (29) (31percent) and (34) (49percent) were obtained; the sulphur compounds were deiodinated in preference to coupling.These reactions are compared with those used previously in myricanol synthesis and the factors affecting ring closure are discussed.Steric effects at the coupling sites appear more important in determining product yield than torsional strain in the products.