19043-03-9

Usage

Uses

Used in Perfumery and Flavoring Industry:
(1R,2R)-(-)-trans-2-methylcyclohexanol is used as a fragrance ingredient and flavoring agent for its distinct minty and cooling properties, enhancing the sensory experience of various consumer products.
Used in Pharmaceutical Industry:
(1R,2R)-(-)-trans-2-methylcyclohexanol is used as a local anesthetic and as a component in over-the-counter medications for coughs and colds, leveraging its cooling effect and soothing properties to alleviate symptoms.
Used in Organic Synthesis:
(1R,2R)-(-)-trans-2-methylcyclohexanol is used as a key intermediate in the synthesis of chiral compounds, playing a significant role in the production of enantiomerically pure substances for pharmaceutical and chemical applications.
Used in Pest Control Products:
(1R,2R)-(-)-trans-2-methylcyclohexanol is used as an insecticide in pest control products, capitalizing on its natural insecticidal properties to manage and control pests effectively.

Upstream product

• 148615-29-6 (1R,2R)-trans-2-methylcyclohexyl octanoate 
• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 95-48-7 ortho-cresol 
• 50539-18-9 (+/-)-cis-2-methylcyclohexanol acetate 
• 82166-21-0 methyl cyclohexane 
• 1373216-32-0 tris(4-isopropylphenyl)silyl chloride 
• 7443-70-1 cis-2-methylcyclohexanol 
• 5726-24-9 Heptanoic acid (R)-2-methyl-cyclohexyl ester 
• 591-49-1 1-methylcyclohex-1-ene 
• 583-59-5 2-Methylcyclohexanol 
• 22554-27-4 (S)-2-methylcyclohexanone 
• 99299-20-4 (2R,4R)-2,4,7-trimethyl-1,5-dioxaspiro[5.5]undecane 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 119068-37-0 ethyl (1S,2R)-2-hydroxycyclohexanecarboxylate 

Downstream Products

• 181962-69-6 Diazo-acetic acid (1R,2R)-2-methyl-cyclohexyl ester 
• 181962-59-4 Diazo-acetic acid (1R,2S)-2-methyl-cyclohexyl ester 
• 583-60-8 2-Methylcyclohexanone 
• 591-49-1 1-methylcyclohex-1-ene 
• 931-11-3 (1R,2R)-2-methyl-1-cyclohexylamine 
• 2133-66-6 2-(trans-2-methylcyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 931-09-9 1-chloro-2-methyl-cyclohexane 
• 35309-56-9 1-iodo-2-methylcyclohexane 
• 5726-20-5 trans-2-Methyl-cyclohexyl-propionat 

Relevant academic research and scientific papers

A crystalline, internally-coordinated chloroborane for asymmetric hydroboration

Asymmetric hydroboration is an important method in the preparation of enantiomerically-enriched compounds that are necessary in many areas of chemistry. Here is reported the preparation of a unique chiral chloroborane-internal ether complex and its applic

Hydrodealkenylative C(sp3)–C(sp2) bond fragmentation

Chemical synthesis typically relies on reactions that generate complexity through elaboration of simple starting materials. Less common are deconstructive strategies toward complexity—particularly those involving carbon-carbon bond scission. Here, we introduce one such transformation: the hydrodealkenylative cleavage of C(sp3)–C(sp2) bonds, conducted below room temperature, using ozone, an iron salt, and a hydrogen atom donor. These reactions are performed in nonanhydrous solvents and open to the air; reach completion within 30 minutes; and deliver their products in high yields, even on decagram scales. We have used this broadly functionality tolerant transformation to produce desirable synthetic intermediates, many of which are optically active, from abundantly available terpenes and terpenoid-derived precursors. We have also applied it in the formal total syntheses of complex molecules.

Catalytic carbonyl hydrosilylations: Via a titanocene borohydride-PMHS reagent system

Reduction of a wide range of aldehydes and ketones with catalytic amounts of titanocene borohydride in concert with a stoichiometric poly(methylhydrosiloxane) (PMHS) reductant is reported. Preliminary mechanistic studies demonstrate that the reaction is mediated by a reactive titanocene(iii) complex, whose oxidation state remains constant throughout the reaction.

P-Tolylimido rhenium(v) complexes with phenolate-based ligands: Synthesis, X-ray studies and catalytic activity in oxidation with tert-butylhydroperoxide

The reactions of mer-[Re(p-NTol)X3(PPh3)2] (X = Cl, Br) with chelating phenolate-based ligands (2-(2-hydroxy-5-methylphenyl)benzotriazole (HL1), 2-(2-hydroxyphenyl)benzothiazole (HL2) or 2-(2-hydroxyphenyl)benzoxazole (HL3)) afforded a series of p-tolylimido rhenium(v) complexes cis- or trans-(X,X)-[Re(p-NTol)X2(L)(PPh3)]·yMeCN (where X = Cl, Br; L = L1, L2, L3 and y = 0-2) and [Re(p-NTol)X(L)(PPh3)2]Z·pPPh3 (where X = Cl, Br; Z = ReO4, PF6; L = L1, L2, L3 and p = 0 or 1). The reported compounds were characterized by elemental analysis, FT-IR, NMR (1H, 13C and 31P) and X-ray crystallography. Interestingly, the halide ions of [Re(p-NTol)Cl2(L1)(PPh3)]·MeCN (1) and [Re(p-NTol)Cl2(L2)(PPh3)]·2MeCN (3) are in cis relative dispositions, whereas the complexes [Re(p-NTol)Br2(L)(PPh3)] (L1 for 2, L2 for 4 and L3 for 6) and [Re(p-NTol)Cl2(L3)(PPh3)] (5) were found to be trans-(X,X) isomers. The compounds [Re(p-NTol)X(L)(PPh3)2](PF6) (X = Cl, Br; L = L1 and L2) and [Re(p-NTol)X(L3)(PPh3)2](PF6)·PPh3 (X = Cl, Br) have been tested in oxidative catalysis. A few compounds exhibited very good catalytic properties in oxidation of alcohols with tert-BuOOH (TBHP) in acetonitrile solution at moderate temperatures. Complex [Re(p-NTol)Cl(L2)(PPh3)2]PF6 (13) is the catalyst of choice for oxidation of 1-phenylethanol to acetophenone (in 80% yield; turnover number attained 290 after 30 h) and cyclooctanol to cyclooctanone (in 88% yield). Notably lower activity has been found in the oxidation of alkanes with TBHP. Product distribution in the oxidation of methylcyclohexane indicates some steric hindrance around the reaction center.

Diastereoselective and Enantioselective Silylation of 2-Arylcyclohexanols

The silylation-based kinetic resolution of trans 2-arylcyclohexanols was accomplished by employing a triaryl silyl chloride as the derivatizing reagent with a commercially available isothiourea catalyst. The methodology is selective for the trans diastereomer over the cis, which provides an opportunity to selectively derivatize one stereoisomer out of a mixture of four. By employing this technology, a facile, convenient method to form a highly enantiomerically enriched silylated alcohol was accomplished through a one-pot reduction-silylation sequence that started with a 2-aryl-substituted ketone.

Cytochrome P450 catalyzed oxidative hydroxylation of achiral organic compounds with simultaneous creation of two chirality centers in a single C-H activation step

Regio- and stereoselective oxidative hydroxylation of achiral or chiral organic compounds mediated by synthetic reagents, catalysts, or enzymes generally leads to the formation of one new chiral center that appears in the respective enantiomeric or diastereomeric alcohols. By contrast, when subjecting appropriate achiral compounds to this type of C-H activation, the simultaneous creation of two chiral centers with a defined relative and absolute configuration may result, provided that control of the regio-, diastereo-, and enantioselectivity is ensured. The present study demonstrates that such control is possible by using wild type or mutant forms of the monooxygenase cytochrome P450 BM3 as catalysts in the oxidative hydroxylation of methylcyclohexane and seven other monosubstituted cyclohexane derivatives.

New p-tolylimido rhenium(v) complexes with carboxylate-based ligands: Synthesis, structures and their catalytic potential in oxidations with peroxides

Novel p-tolylimido rhenium(v) complexes trans-(Cl,Cl)-[Re(p-NC 6H4CH3)Cl2(pyz-2-COO)(PPh 3)]·MeCN (1), trans-(Cl,Cl)-[Re(p-NC6H 4CH3)Cl2(pyz-2-COO)(PPh

CYCLIC AMINE-1-CARBOXYLIC ACID ESTER DERIVATIVE AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME

Provided is a compound useful as a therapeutic drug for pain and inflammation caused by various pathological conditions such as neuropathic pain and rheumatoid arthritis. The compound of the formula (I) or a salt thereof [wherein R1 is a methyl group or a hydrogen atom, R2 represents a hydrogen atom, an alkyl group, an alkylcarbonyl group or an aryl carbonyl group, A represents a cycloalkyl group, a cycloalkenyl group, an aryl group or a heteroaryl group (each group may be substituted with a substituent selected from the group consisting of alkyl, alkenyl, cycloalkyl and halogen), n and m each represent an integer of 1, 2 or 3, and p represents an integer of 0, 1, 2 or 3].

CYCLIC AMINE-1-CARBOXYLIC ACID ESTER DERIVATIVE AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME

Provided is a compound useful as a therapeutic drug for pain and inflammation caused by various pathological conditions such as neuropathic pain and rheumatoid arthritis. The compound of the formula (I) or a salt thereof [wherein R1 is a methyl group or a hydrogen atom, R2 represents a hydrogen atom, an alkyl group, an alkylcarbonyl group or an aryl carbonyl group, A represents a cycloalkyl group, a cycloalkenyl group, an aryl group or a heteroaryl group (each group may be substituted with a substituent selected from the group consisting of alkyl, alkenyl, cycloalkyl and halogen), n and m each represent an integer of 1, 2 or 3, and p represents an integer of 0, 1, 2 or 3].

Oxidation of organotrifluoroborates via oxone

A method for the oxidation of organotrifluoroborates using Oxone was developed. A variety of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates were converted into the corresponding oxidized products in excellent yields. This method proved to be tolerant of a broad range of functional groups, and in secondary alkyl substrates it was demonstrated to be completely stereospecific.