76155-27-6

Upstream product

• 96836-97-4 diethyl cyclohexane-trans-1,2-dicarboxylate 
• 13149-04-7 (rac)-trans-4,5-bis(hydroxymethyl)cyclohex-1-ene 
• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 14166-21-3 (+/-)-trans-1,2-cyclohexanedicarboxylic anhydride 
• 3710-30-3 1,7-Octadiene 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 4841-85-4 trans-1,2-bis(ethoxycarbonyl)-4-cyclohexene 
• 2207-01-4 cis-1,2-dimethylcyclohexane 
• 3205-35-4 trans dimethyl cyclohexane-1,2-dicarboxylate 

Downstream Products

• 66347-68-0 (±)-(1S, 2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate) 
• 57280-65-6 trans-2-(hydroxymethyl)cyclohexanecarboxylic acid 
• 65376-05-8 (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane 
• 3205-34-3 (1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane 
• 65376-04-7 (-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid 
• 3205-36-5 trans-1,2-bis(hydroxymethyl)cyclohexane di-p-toluene-sulfonate 
• 137303-14-1 trans-1-methoxymethyl-2-hydroxymethylcyclohexane 

Relevant academic research and scientific papers

Novel nitrile oxide cycloaddition approach towards papuamine: Stereoselective synthesis of a potentially useful trans-hydrindane intermediate

In a potentially useful approach to the marine alkaloid papuamine 1, a known trans-hydrindane intermediate 17 has been synthesised in racemic form using a model sequence of reactions involving a nitrile oxide cycloaddition as a key step.

Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds

Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.

Carbonylation of ethylenically unsaturated compounds

A process for the carbonylation of ethylenically unsaturated compounds including vinyl esters and a process for the production of 3-hydroxy propanoate esters or acids. The process comprises reacting said compound with carbon monoxide in the presence of a source of hydroxyl groups and of a catalyst system. The catalyst system is obtainable by combining: (a) a metal of Group 8, 9 or 10 or a compound thereof: and (b) a bidentate ligand of general formula (I): X1(X2)-Q2-A-R—B-Q1-X3(X4).

CARBONYLATION OF ETHYLENICALLY UNSATURATED COMPOUNDS

PROBLEM TO BE SOLVED: To provide a process for the carbonylation of ethylenically unsaturated compounds including vinyl esters and a process for the production of 3-hydroxypropanoate esters or 3-hydroxypropanoic acids. SOLUTION: The process comprises reacting the compound with carbon monoxide in the presence of a source of hydroxyl groups and of a catalyst system. The catalyst system is obtainable by combining: (a) a metal of Group 8, 9 or 10 or a compound thereof: and (b) a bidentate ligand of general formula (I): X1(X2)-Q2-A-R-B-Q1-X3(X4). COPYRIGHT: (C)2015,JPOandINPIT

Discovery of octahydroindenes as PAR1 antagonists

Octahydroindene was identified as a novel scaffold for protease activated receptor 1 (PAR1) antagonists. Herein, the 2-position (C2) was explored for structure-activity relationship (SAR) studies. Compounds 14, 19, and 23b showed IC50 values of 1.3, 8.6, and 2.7 nM in a PAR1 radioligand binding assay, respectively, and their inhibitory activities on platelet activation were comparable to that of vorapaxar in a platelet rich plasma (PRP) aggregation assay. This series of compounds showed high potency and no significant cytotoxicity; however, the compounds were metabolically unstable in both human and rat liver microsomes. Current research efforts are focused on optimizing the compounds to improve metabolic stability and physicochemical properties as well as potency.

[6+5] FUSED BICYCLES AS A THROMBIN ANTAGONIST, PROCESS FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE BICYCLES

The present invention relates to the new [6+5] fused bicycle derivatives, pharmaceutically acceptable salts or isomers thereof, processes for preparing the same, and pharmaceutical compositions comprising the same. The [6+5] fused bicycle derivatives can antagonize the thrombin receptor and thus may be effectively used for the treatment and prevention of thrombus, platelet aggregation, atherosclerosis, restenosis, blood coagulation, hypertension, arrhythmia, angina pectoris, heart failure, inflammation and cancer when used alone or with other cardiovascular agents.

Characterization and alkane oxidation activity of a diastereopure seven-coordinate iron(III) alkylperoxo complex

Spectroscopic characterization and alkane oxidation studies of a diastereopure seven-coordinate high-spin iron(iii) alkylperoxo complex based on the chiral N,N′,N-bis(l-prolinate)pyridine ligand Py(ProMe)2 (1) are reported. The Royal Society of Chemistry 2007.

A mechanistic study on the intramolecular ionic Diels-Alder reaction of 2-methyl-3,9,11-tridecatriene-2-ol and 2,11-dimethyl-1,3,9,11-dodecatetraene

Intramolecular ionic Diels-Alder reaction of 2-methyl-3,9,11-tridecatriene-2-ol (1) was studied under acidic conditions. Treatment of 2-methyl-3,9,11-tridecatriene-2-ol (1) with trifluoromethanesulfonic acid yielded 7-methyl-8-isopropenyl-1,2,3,4,4aR

Synthesis of α,β-unsaturated dioxanes, dioxolanes and dioxepanes by trans-acetalisation of dimethylacetals with meso or C 2-symmetrical 1,2-, 1,3- and 1,4-diols

Several o-dibenzylic diols were prepared reacting organometallics with o-phthalaldehyde at room temperature in ether. The identity of the meso and C2-symmetrical (D,L) isomers as well as their ratio were determined by chiral gas chromatography. The meso and C2 (racemic) stereoisomeric diols were easily separated by flash chromatography on silica gel. A set of 18 α,β-unsaturated acetals were then prepared reacting those, as well as commercially available 1,2, 1,3 and 1,4 diols, with the corresponding methylacetals in acidic medium. A trans-acetalisation procedure adapted to the cases of fragile allylic alcohols or unfavorable 1,6 diols-derived dioxonanes based on a Dean-Stark trapping of methanol was also employed.

Hydrolysis of cyclic orthoesters: Experimental observations and theoretical rationalization

Reaction products using labelled water (H2O18) and the relative rate of hydrolysis of the four bicyclic orthoesters 1-4 having a six or a seven-membered orthoester ring are reported. With the help of theoretical calculations (semi-empirical AM1 and ab initio 3-21G level), the results are explained by taking into account proton affinities as well as steric and stereoelectronic effects.