143365-54-2

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 51171-72-3 4-phenylcyclohex-2-en-1-one 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 6312-13-6 3-methyl-4-phenylcyclohex-2-en-1-one 
• 205391-14-6 6,6-dimethoxy-4-phenylhexanoic acid 
• 71911-76-7 1,2,3,4-tetrahydro-[1,1'-biphenyl]-4-ol 
• 1133717-15-3 (S)-4-phenylcyclohexenone 
• 1286679-08-0 4-phenylbicyclo[4.1.0]heptan-1-ol 

Relevant academic research and scientific papers

Boron Trifluoride-Mediated Cycloaddition of 3-Bromotetrazine and Silyl Enol Ethers: Synthesis of 3-Bromo-pyridazines

Pyridazines are important scaffolds for medicinal chemistry or crop protection agents, yet the selective preparation of 3-bromo-pyridazines with high regiocontrol remains difficult. We achieved the Lewis acid-mediated inverse electron demand Diels-Alder reaction between 3-monosubstituted s-tetrazine and silyl enol ethers and obtained functionalized pyridazines. In the case of 1-monosubstituted silyl enol ethers, exclusive regioselectivity was observed. Downstream functionalization of the resulting 3-bromo-pyridazines was demonstrated utilizing several cross-coupling protocols to synthesize 3,4-disubstituted pyridazines with excellent control over the substitution pattern.

Synthesis of Acyl Fluorides via DAST-Mediated Fluorinative C-C Bond Cleavage of Activated Ketones

A new protocol for preparation of acyl fluorides was developed by recognizing activated ketones as starting materials. The method provides a different scope compared with previously reported methods that employ carboxylic acids as substrates. A working hypothesis of pull-and-push-driven fluorinative C-C bond cleavage was successfully demonstrated by the simple addition of diethylaminosulfur trifluoride (DAST) derivatives to α-oximinoketones. The designed reaction system led to a highly efficient and chemoselective reaction. The wide availability of the ketones allowed for a range of synthetically useful aryloyl and aliphatic acyl fluorides including those containing chiral skeletons. The method is mild, fast, scalable, and potentially one-pot operative.

Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones

Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.

Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones

Di-tert-butylmagnesium has been found to be a reactive, yet non-nucleophilic and non-reductive, carbon-centred base for the deprotonation of a series of ketones. This reagent demonstrates equally high reactivity when used as either the pre-formed reagent, or in a more accessible one-pot protocol from the parent Grignard reagent, and offers improved atom-efficiency over more traditionally employed bases. Georg Thieme Verlag Stuttgart.

Synthesis of 5-substituted 4,5,6,7-tetrahydroindoles from cyclohexanones

5-Substituted 4,5,6,7-tetrahydroindoles were prepared from 4-substituted cyclohexanones in three steps: conversion to an enol silyl ether, introduction of a formylmethyl group at 2-C, and the Paal-Knorr pyrrole synthesis by reacting the 1,4-dicarbonyl compounds with ammonia. The substituents are H, methyl, ethyl, tert-butyl, methoxy, and phenyl.

Bismesitylmagnesium: A thermally stable and non-nucleophilic carbon-centred base reagent for the efficient preparation of silyl enol ethers

Bismesitylmagnesium has been established as an accessible, practical, convenient, and non-nucleophilic carbon-centred base reagent for efficient access to silyl enol ethers from a series of ketone substrates at readily utilisable temperatures. The Royal Society of Chemistry.

3-mercaptoacetylamino-1,5-substituted-2-oxo-azepan derivatives useful as inhibitors of matrix metalloproteinase

The present invention relates to certain novel 3-mercaptoacetylamino-1,5-substituted-2-oxo-azepan derivatives useful as inhibitors of matrix metalloproteinase. Pharmaceutical compositions containing said compounds as well as methods of treating various disease states responding to inhibition of matrix metalloproteinase are also claimed herein.

GUANIDINE DERIVATIVES AND USE THEREOF AS NEUROPEPTIDE FF RECEPTOR ANTAGONISTS

The invention relates to guanidine derivatives of formula (I) where: A = a chain of 3-c6 carbon atoms, one of which can be replaced by -N(R')- or -O- and R' = H or a substituent, where the ring skeleton only contains both double bonds of the thiazole component, the pharmaceutically-acceptable acid addition salts of basic compounds of formula (I), the pharmaceutically-acceptable salts of compounds of formula (I),, comprising acid groups, with bases, the pharmaceutically-acceptable esters of hydroxy or carboxyl group containing compounds of formula (I) and the solvates or hydrates thereof, which are partly known and partly novel and exhibit a neuropeptide FF receptor antagonist effect. The above are suitable for the treatment of pain and hyperalgesia, withdrawal symptoms in alcohol, psychotropic and nicotine dependencies, for improvement or cure of said dependencies, for regulation of insulin excretion, food intake, memory functions, blood pressure, electrolyte and energy management and for treatment of urinary incontinence. The above can be produced using generally used methods and processed to give medicaments.

1-Carboxymethyl-2-oxo-azepan derivatives useful as selective inhibitors of MMP-12

The present invention relates to certain novel 1-carboxymethyl-2-oxo-azepan derivatives of the formula useful as inhibitors of matrix metalloproteinases (MMPs). The compounds of formula (1) are especially useful as selective inhibitors of MMP-12. Pharmaceutical compositions containing said compounds as well as methods of treating various disease states responding to inhibition of matrix metalloproteinase are also claimed herein.

Friedel-crafts reactions of a sulfonyl-substituted vinylic epoxide with various aromatics

The Friedel-Crafts reactions of a sulfonyl-substituted vinylic epoxide with various aromatic compounds were discussed. A reaction between vinylic epoxide, benzene and BF3OEt2 slightly increased the stereoselectivity. Thiophene reacted well without added amine and produced four product isomers. The 1H NMR signals from C(4)H in these isomers were well separated and indicated the presence of two trans isomers and two cis isomers.