64543-48-2

Basic information

• Product Name: 2-Cyclohexen-1-ol, 3,5,5-trimethyl-, (S)-
• CAS NO: 64543-48-2
• Molecular Formula: C9H16O
• Molecular Weight: 140.225
• Mol File: 64543-48-2.mol

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-ol, 3,5,5-trimethyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-ol, 3,5,5-trimethyl-, (S)-(64543-48-2)
• EPA Substance Registry System: 2-Cyclohexen-1-ol, 3,5,5-trimethyl-, (S)-(64543-48-2)

Safety Data

• Hazardous Substances Data: 64543-48-2(Hazardous Substances Data)

Upstream product

• 470-99-5 isophorol 
• 25866-59-5 1,5,5-trimethylcyclohexa-1,3-diene 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 108-05-4 vinyl acetate 

Downstream Products

• 1073591-10-2 (S)-3,5,5-trimethyl-2-cyclohexen-1-yl propionate 
• 663919-82-2 ethyl (S)-(1,5,5-trimethyl-2-cyclohexen-1-yl)acetate 
• 1073591-09-9 (S)-3,5,5-trimethyl-2-cyclohexen-1-yl acetate 
• 1073591-11-3 (S)-3,5,5-trimethyl-2-cyclohexen-1-yl butyrate 

Relevant articles and documents

Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand

The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2-((2R,5R)-2,5-dimethyl-phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non-noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity. (Figure presented.).

Synthesis of (+)-Darwinolide, a Biofilm-Penetrating Anti-MRSA Agent

Darwinolide, a recently identified marine natural product from the Antarctic sponge Dendrilla membranosa, was previously shown to exhibit promising activity against the biofilm phase of methicillin-resistant Staphylococcus aureus. Its challenging tetracyclic rearranged spongian diterpenoid structure links a trimethylcyclohexyl subunit to a seven-membered core with two fused tetrahydrofuran units. Herein, we describe the first synthesis of (+)-darwinolide, which features a convergent aldol fragment coupling, an Ireland–Claisen rearrangement, and an organocatalytic desymmetrization as the key steps. Our results provide a foundation for the development of novel antibiofilm-specific antibiotics.

CHIRAL METAL COMPLEX COMPOUNDS

The invention comprises novel chiral metal complex compounds of the formula (I) wherein M, PR2, R3 and R4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

A process for preparing optically active aldehyde or ketone method and catalyst preparation method

The invention provides a method for preparing optically active aldehyde or ketone by asymmetric hydrogenation and a preparation method of a catalyst thereof. The optically active aldehyde or ketone is prepared by using a homogeneous and optically active double transition metal catalyst and a chiral amino acid cocatalyst through asymmetric hydrogenation of alpha, beta-unsaturated aldehyde or ketone. The reaction pressure (absolute pressure) is 0.1-10MPa, preferably 5-8MPa; the reaction temperature is 25-90 DEG C; the catalyst is prepared from chiral multi-coordination phosphine-containing ligands and transition metals; chiral amino acid added to the reaction system serves as a cocatalyst; and the reaction selectivity is 95-99%, the conversion rate can reach 85-99.9%, and the optical purity of the product is 80-99ee%.

Manganese(I)-Catalyzed Enantioselective Hydrogenation of Ketones Using a Defined Chiral PNP Pincer Ligand

A new chiral manganese PNP pincer complex is described. The asymmetric hydrogenation of several prochiral ketones with molecular hydrogen in the presence of this complex proceeds under mild conditions (30–40 °C, 4 h, 30 bar H2). Besides high catalytic activity for aromatic substrates, aliphatic ketones are hydrogenated with remarkable selectivity (e.r. up to 92:8). DFT calculations support an outer sphere hydrogenation mechanism as well as the experimentally determined stereochemistry.

Synthesis of chiral odoriferous oxy-derivatives of 1,5,5- trimethylcyclohexene

Ten racemic and ten enantiomeric pairs of odoriferous compounds, mainly esters, were obtained from isophorone. The starting material, isophorone was reduced to racemic isophorol, which was resolved in pure enantiomers via the lipase catalyzed esterification. The next steps of syntheses, orthoacetic Claisen rearrangement, reduction of esters, esterification of alcohols or their oxidation were carried out with the racemic and enantiomerically enriched (above 98% ee) compounds. The propionates of isophorol (7, 7a, 7b) and 2-(1,5,5-trimethyl-2-cyclohexen-1-yl)ethanol (10, 10a, 10b) possess the most valuable odoriferous properties, useful for cosmetic and food industries.

Enantioselective Synthesis of Cycloalkenols by Monohydroboration of 1,3-Cycloalkadienes with Diisocaranylboranes

Representative 1,3-cycloalkadienes were monohydroborated with di-(2-isocaranyl)borane (2-Icr2BH) and di-(4-isocaranyl)borane (4-Icr2BH) of high optical purity (>99percent ee).An efficient procedure for the oxidation of the intermediate allylic organoboranes at low temperature has been developed. 2-Cycloalkenols of moderate to high optical purity (68-96percent ee) were obtained from 2-Icr2BH and unsubstituted 6-8 membered ring dienes whereas 4-Icr2BH showed lower enantioselectivity. 1,3-Cyclopentadiene gave exclusivelly 3-cyclopentenol with both reagents.Methyl-substituted 1,3-cyclohexadienes produced corresponding 2- or 3-cyclohexenols depending on the substitution pattern of the diene. asymmetric hydroboration, conjugated cycloalkadienes, 2-cycloalkenols

Alkylmetal Asymmetric Reduction. 13. A Sterically Crowded Chiral Organoaluminum Compound as a Reducing Agent of Ketones

Optically active carbinols were obtained by reducing the corresponding ketones with heptan-2-yl>methyl>aluminum dichloride.The reactions, which have been carried out at room temperature, are fast and afforded the carbinols in good chemical and optical yields.The extent of the enantioselectivity, along with the stereochemistry of the process, was found to depend on the structure of the ketone employed.The overall results indicated that the present reducing method may be a convenient route to obtain secondary alcohols of high enantiomeric purity under mild conditions.

Metal Catalysis in Organic Reactions. 16. Conjugate Reduction of α,β-Unsaturated Ketones by Trialkylalane-Nickel Systems

The reaction between triisobutylaluminum and α,β-unsaturated ketones, in pentane at room temperature, leads to products which correspond to 1,2-reduction and 1,2-addition processes.The extent of such reactions is dependent on both the structure of the enone and the reagent-to-substrate ratio.Under the same experimental conditions, bis(N-methylsalicylaldimine)nickel catalyzes the conjugate reduction of α,β-enones by triisobutylaluminum; acyclic and cyclic enones have been converted into the corresponding saturated ketones in good to excellent yields.The catalytic process is discussed in terms of a catalytic cycle involving a hydridonickel species.