15753-50-1

Usage

Uses

Used in Pharmaceutical Industry:
CIS-1,2-CYCLOHEXANEDIMETHANOL is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to be incorporated into complex molecular structures. One such application is in the synthesis of 9-[(Z)-2(hydroxymethyl)cyclohexyl]methylguanine, a compound with potential therapeutic properties.
Used in Chemical Synthesis:
CIS-1,2-CYCLOHEXANEDIMETHANOL is used as a building block in the chemical synthesis of various organic compounds due to its reactive functional groups and unique structural features. Its versatility allows it to be employed in the creation of a wide range of products, from pharmaceuticals to specialty chemicals.
Used in Research and Development:
CIS-1,2-CYCLOHEXANEDIMETHANOL is utilized as a research compound for studying its chemical properties and potential applications in various fields. Its unique structure and reactivity make it an interesting subject for scientific investigation, which could lead to the discovery of new applications and uses.

InChI:InChI=1/C8H16O2/c9-5-7-3-1-2-4-8(7)6-10/h7-10H,1-6H2/t7-,8+

Upstream product

• 17351-07-4 diethyl cyclohexane-cis-1,2-dicarboxylate 
• 439919-46-7 cis-1,6-dihydroxymethyl-3-cyclohexene 
• 85-42-7 1,2-Cyclohexanedicarboxylic acid-anhydride 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 84-66-2 Diethyl phthalate 
• 1687-29-2 dimethyl cis-1,2-cyclohexanedicarboxylate 
• 2484-60-8 cyclohexane-1,2-dicarboxylic acid monomethyl ester 
• 130279-51-5 Phosphorous acid diethyl ester (1S,2R)-2-formyl-cyclohexylmethyl ester 
• 3710-30-3 1,7-Octadiene 
• 235780-27-5 cis-1,2-Cyclohexanedimethyl bis[N-(2-hydroxy-1,1-dimethylethyl)carbamate] 
• 2207-01-4 cis-1,2-dimethylcyclohexane 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 103668-33-3 3-hydroxymethylcyclohexene 
• 610-09-3 (1R,2S)-cyclohexane-1,2-dicarboxylic acid 

Downstream Products

• 13019-30-2 (±)-1,2-bis(bromomethyl)cyclohexane 
• 59461-66-4 cis-cyclohexane-1,2-diyldimethyl ditosylate 
• 98516-00-8 cis-1,2-cyclohexanedimethanol diacetate 
• 1118-90-7 L-homoglutamic acid 
• 89395-29-9 (3aR,7aS)-hexahydroisobenzofuran-1-one 
• 13149-01-4 cis-8-oxabicyclo<4.3.0>nonane 
• 2819-48-9 1,2-bis(methylene)cyclohexane 
• 98516-09-7 cis-1-(acetoxymethyl)-2-(hydroxymethyl)cyclohexane 
• 65376-02-5 (1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one 
• 131-62-4 1-hydroxy-1,2-benzodioxol-3-(1H)-one 
• 51555-65-8 cyclohexane-1,2-dicarbaldehyde 
• 235779-96-1 cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate) 

Relevant academic research and scientific papers

Stereoselectivity in intramolecular diene cyclozirconation: A combined experimental and theoretical approach

Intramolecular diene cyclozirconation (1 → 2 + 3 → 4) can be highly diastereoselective (97:3 trans/cis for 4). It is suggested that the cis and trans diastereomers of the zirconacycle are equilibrating under the conditions of the reaction, and that the observed diastereomeric preference of 4 reflects the relative stability of the two diastereomeric zirconacycles. Results for the intramolecular cyclozirconation of two other dienes, 8 and 14, as well as for the "heterodiene" N,N-diallylaniline are also reported. Computational results at the molecular mechanics, semiempirical molecular orbital ZINDO and nonlocal density functional theory levels are used to explain the observed stereochemistry in terms of thermodynamic and kinetic control.

Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids

Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.

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.

Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones

In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol (2a) and decane-1,5-diol (3a) into the corresponding γ- (2b) and δ-decalactones (3b) with yield of 80% and enantiomeric excess (ee)?=?75% and ee?=?90%, respectively. Among oxidation of meso diols, (?)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee?=?76% as well as (?)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee?=?90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623–627, 2016.

Microbial alcohol dehydrogenase screening for enantiopure lactone synthesis: Down-stream process from microtiter plate to bench bioreactor

One-pot conversion with whole cells of bacteria was performed for biooxidation of meso monocyclic (3a-b) and bicyclic diols (3c-e) into corresponding chiral lactones of bicyclo[4.3.0]nonane structure (2a-b) as well as exo- and endo-bridged lactones with the structure of [2.2.1] (3c-d) and [2.2.2] (3e). Micrococcus sp. DSM 30771 was selected as biocatalyst with significant alcohol dehydrogenase activity. Among tested strains, microbial oxidation of meso diols 3a-e catalyzed by Micrococcus sp. afforded enantiomerically pure ((+)-(2S,3R)-2c (ee = 99%), (+)-(2S,3R)-2e (ee = 99%)) or enriched ((+)-(1S,5R)-2a (ee = 90%), (-)-(1S,5R)-2b (ee = 86%), (+)-(2S,3R)-2d (ee = 80%)) lactone moieties. Comparative study with respect to microbial cultivation as well as biooxidation was undertaken to verify agreement of secondary metabolite biosynthesis in different scales: from MTP (4 mL), across shake flask (100 mL) till bioreactor (4 L). The results from biotransformations showed quite similar dependence in oxidation of all substrates 3a-e in MTP and flasks as well, thereby confirmed the validity and reasonable approach of using MTP for preliminary studies.

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.

Fungistatic activity of bicyclo[4.3.0]-γ-lactones

Five optically active and sixteen racemic lactones (nine of them new) of bicyclo[4.3.0]nonane structure were synthesized. IC50 values for the following phytopathogens were determined: Aspergillus ochraceus AM 456, Fusarium culmorum AM 282, Fusarium oxysporum AM 13, Fusarium tricinctum AM 16. Effect of compound structures, especially stereogenic centers, on fungistatic activity has been discussed. The highest fungistatic activity was observed for trans-7,8-dibromo-cis-3-oxabicyclo[4.3.0]nonan-2-one (3c), IC50 = 30.1 μg/mL (0.10 μM/mL), and cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2- one (3b), IC50 = 72.2 μg/mL (0.47 μM/mL), toward F. oxysporum AM 13.

[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.

Dihalocarbene insertion reactions into C-H bonds of compounds containing small rings: Mechanisms and regio- and stereoselectivities

(Chemical Equation Presented) Novel insertion reactions of dichloro- and dibromocarbene into carbon-hydrogen bonds adjacent to cyclopropane rings are reported. It is found that the predominant isomers formed in the reactions with bicyclo[4.1.0]heptane result from insertion into the endo carbon-hydrogen bonds alpha to the three-membered ring. In the reactions of bicyclo[3.1.0]hexane, however, the exo dihalocarbene insertion products are formed as the major isomers. In some compounds cyclopropane rings "activate" adjacent carbon-hydrogen bonds, whereas other systems containing three-membered rings do not. Moreover, the influence of various substituents (methyl, geminal dimethyl, phenyl, methoxy, and ethoxy) attached to bicyclo-[3.1.0]hexane and bicyclo[4.1.0]heptane in dihalocarbene reactions has been studied. The findings can be explained by the concept of maximum orbital overlaps of Walsh orbitals of the cyclopropane rings and the α carbon-hydrogen bonds. In stark contrast, selective insertion into the tertiary carbon-hydrogen bonds of the cyclobutane ring in bicyclo[4.2.0]octane is observed.

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.