13856-87-6

Upstream product

• 109-72-8 n-butyllithium 
• 104-88-1 4-chlorobenzaldehyde 
• 18987-26-3 trimethyltelluronium iodide 
• 122-56-5 tributyl borane 
• 693-03-8 n-butyl magnesium bromide 
• 109-65-9 1-bromo-butane 
• 13940-94-8 (4-chlorophenyl)dichloromethane 
• 19350-69-7 4-chlorobenzaldehyde p-toluenesulfonylhydrazone 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 693-04-9 butyl magnesium bromide 
• 71-23-8 propan-1-ol 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 25017-08-7 1-(4-chlorophenyl)pentan-1-one 

Downstream Products

• 15954-52-6 p-Chlor-β-butyl-hydrozimtsaeure 
• 50673-59-1 Bernsteinsaeure-mono-<1-(4-chlorphenyl)-pentyl>-ester 
• 50673-77-3 Pentanedioic acid mono-[1-(4-chloro-phenyl)-pentyl] ester 
• 25017-08-7 1-(4-chlorophenyl)pentan-1-one 
• 18654-74-5 (E)-1-chloro-4-(pent-1-en-1-yl)benzene 
• 426215-79-4 4-(4-chloro-phenyl)-5-propyl-thiazol-2-ylamine 

Relevant academic research and scientific papers

Control of enantioselectivity in the enzymatic reduction of halogenated acetophenone analogs by substituent positions and sizes

We utilized acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD), wild type and Trp288Ala mutant, to reduce halogenated acetophenone analogs to their corresponding (S)- and (R)-alcohols beneficial as pharmaceutical intermediates. Reduction by wild type resulted in excellent (S)-enantioselectivity for all of the substrates tested. Meanwhile, reduction by Trp288Ala resulted in high (R)-enantioselectivity for the reduction of 4′ substituted acetophenone and 2′-trifluoromethylacetophenone. In addition to that, we were able to control the enantioselectivity of Trp288Ala by the positions and sizes of the halogen substituents.

A sustainable multicomponent pyrimidine synthesis

Since alcohols are accessible from indigestible biomass (lignocellulose), the development of novel preferentially catalytic reactions in which alcohols are converted into important classes of fine chemicals is a central topic of sustainable synthesis. Multicomponent reactions are especially attractive in organic chemistry as they allow the synthesis of large libraries of diversely functionalized products in a short time when run in a combinatorial fashion. Herein, we report a novel, regioselective, iridium-catalyzed multicomponent synthesis of pyrimidines from amidines and up to three (different) alcohols. This reaction proceeds via a sequence of condensation and dehydrogenation steps which give rise to selective C-C and C-N bond formations. While the condensation steps deoxygenate the alcohol components, the dehydrogenations lead to aromatization. Two equiv of hydrogen and water are liberated in the course of the reactions. PN5P-Ir-pincer complexes, recently developed in our laboratory, catalyze this sustainable multicomponent process most efficiently. A total of 38 different pyrimidines were synthesized in isolated yields of up to 93%. Strong points of the new protocol are its regioselectivity and thus the immediate access to pyrimidines that are highly and unsymmetrically decorated with alkyl or aryl substituents. The combination of this novel protocol with established methods for converting alcohols to nitriles now allows to selectively assemble pyrimidines from four alcohol building blocks and 2 equiv of ammonia.

Catalytic asymmetric addition of alkyllithium reagents to aromatic aldehydes

Herein, we report the first efficient catalytic system for the asymmetric alkylation of aldehydes with organolithium reagents in the presence of titanium(IV) isopropoxide. A variety of alkyllithium reagents can be added to aromatic aldehydes in good yields with high enantioselectivities in a simple one-pot procedure under mild conditions. Herein, we report the first efficient catalytic system for the asymmetric alkylation ofaldehydes with organolithium reagents in the presence of titanium(IV) isopropoxide. A variety of alkyllithium reagents can be added to aromatic aldehydes in good yields with high enantioselectivities in a simple one-pot procedure under mild conditions. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

A novel one-pot synthesis of secondary alcohols from esters

Alkylation or vinylation by using organometallic reagents after partial reduction of carboxylic esters with LDBBA gave secondary alcohols, also involving allyl alcohols, without any isolation of intermediates in good yield (54-78%).

Efficient chemoselective addition of grignard reagents to carbonyl compounds in 2-methyltetrahydrofuran

Compared with tetrahydrofuran (THF) as a solvent for the addition reactions between Grignard reagents and carbonyl compounds 2-methyltetrahydrofuran affords the corresponding adducts in higher yields with higher chemoselectivities. Moreover, 2-methyltetrahydrofuran can be readily recycled and reused, which lowers the cost of the process and makes the reaction greener.

Bronsted acid-catalyzed benzylation of 1,3-dicarbonyl derivatives

The direct alkylation of 1,3-dicarbonyl compounds with benzylic alcohols is shown to be efficiently catalyzed by simple Bronsted acids such as triflic acid (TfOH) and p-toluenesulfonic acid (PTS) to give rise to monoalkylated dicarbonyl derivatives in high yields. In the absence of the nucleophile, substituted alkenes, generated through a formal dimerization reaction, are obtained. The reactions are carried out in air using undried solvents, with water being the only side product of the process.

The ritter reaction under truly catalytic bronsted acid conditions

Simple organic acids like 2,4-dinitrobenzenesulfonic acid (DNBSA) catalyze the Ritter reaction of secondary benzylic alcohols giving rise to the corresponding N-benzylacetamides in usually high yields. Reactions can be conducted without exclusion of oxygen and without the need of dry solvents. With tertiary α,α-dimethylbenzylic alcohols a different pathway involving a formal dimerization reaction takes place under the acid-catalytic conditions used. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

17-Beta hydroxysteroid dehydrogenase type 3 inhibitors for the treatment of androgen dependent diseases

There are disclosed compounds of the formula (I): prodrugs thereof, or pharmaceutically acceptable salts of the compounds or of said prodrugs which are useful as inhibitors of Type 3 17β-Hydroxysteroid Dehydrogenase. Also disclosed are pharmaceutical compositions containing said compounds and their use for the treatment or prevention of androgen dependent diseases.

Sulfonylated aminothiazoles as new small molecule inhibitors of protein phosphatases

Based on a previously identified lead structure, SC-ααδ9, we have developed a versatile new chemical scaffold that can be readily modified to generate libraries of both Tyr and dual specificity phosphatase inhibitors with reduced molecular weight and lipophilicity. The most potent analogue identified to date, aminothiazole 8z, inhibits the dual specificity phosphatase Cdc25B with a Ki of 4.6 ± 0.4 μM and a Hill coefficient of 2.

A facile one-pot synthesis of alkylarylcarbinols from α,α-dichloroarylmethanes and trialkylboranes in the presence of magnesium or lithium

α-Chlorobenzylmagnesium chloride or α-chlorobenzyllithium generated from α,α-dichloroarylmethane and magnesium or lithium, reacts in situ with trialkylboranes in THF at room temperature to produce the corresponding alkylarylcarbinols in good yields after oxidation with sodium perborate.