21651-84-3

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S)-2-METHYLAMINO-CYCLOHEXANOL is used as a chiral auxiliary for the synthesis of pharmaceuticals, leveraging its precise stereochemistry to control the chirality of reactions and produce enantiomerically pure products. This ensures the desired biological activity and therapeutic efficacy of the resulting drugs.
Used in Agrochemical Industry:
In the agrochemical sector, (1S,2S)-2-METHYLAMINO-CYCLOHEXANOL serves as a chiral auxiliary in the synthesis of agrochemicals, contributing to the development of enantiomerically pure compounds with targeted biological activity, which is crucial for effective pest control and crop protection.
Used in the Preparation of Biologically Active Compounds:
(1S,2S)-2-METHYLAMINO-CYCLOHEXANOL is utilized as a building block in the preparation of biologically active compounds, capitalizing on its structural properties to create new molecules with potential applications in various fields, including medicine and biotechnology.

Upstream product

• 20431-81-6 rac-trans-2-methylamino-cyclohexanol 
• 24796-87-0 2-bromo-cyclohexanol 
• 74-89-5 methylamine 
• 260392-51-6 (1S,2S)-2-(N_β-t-butoxycarbonyl-N_α-methylhydrazino)cyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 38898-70-3 cis-2-amino-cyclohexanol-⁽¹⁾ 
• 80-48-8 methyl p-toluene sulfonate 
• 6628-80-4 trans-2-chlorocyclohexanol 
• 32634-68-7 (2S,3S)-di-4-toluoyltartaric acid 
• 853953-24-9 (1S,2S)-2-methylamino-cyclohexanol (S)-mandelic acid salt 
• 218964-40-0 trans-2-(1-methylhydrazino)-1-cyclohexanol 
• 100868-93-7 trans-2-methylaminocyclohexanol hydrochloride 

Downstream Products

• 680231-06-5 (2,3-trans)-N-[(1S,2S)-2-hydroxycyclohexyl]-N-methyl-3-phenyloxirane-2-carboxamide 
• 853953-24-9 (1S,2S)-2-methylamino-cyclohexanol (S)-mandelic acid salt 
• 67198-31-6 trans-N-Benzyl-N,N',N'-trimethyl-1,2-cyclohexanediamine p-toluene sulfonate 
• 90227-79-5 cis-(2-Hydroxy-cyclohexyl)-methyl-aminomethan-sulfonsaeure 
• 116203-82-8 N-nitrosomethyl-N-2-oxocyclohexylamine 
• 882409-15-6 (1R,2S)-cis-2-(N-methyl)amino-1-cyclohexanol 
• 112708-89-1 (1S,2R)-cis-2-(N-methyl)amino-1-cyclohexanol 
• 196699-09-9 (1S,2S)-2-methoxy-N,N-dimethylcyclohexanamine 
• 51066-08-1 7-methyl-7-azabicyclo[4.1.0]heptane 
• 67198-53-2 trans-N-methyl-2-(1-pyrrolidinyl)-cyclohexanamine 
• 260392-65-2 (1R,2S)-2-Methylamino-cyclohexanol; hydrochloride 
• 112708-86-8 (1S,2S)-trans-2-(N-benzoyl-N-methyl)amino-1-cyclohexanol 
• 29783-01-5 trans-2-(dimethylamino)cyclohexanol 

Relevant academic research and scientific papers

Method for synthesizing trans-cyclohexanedimethanamine

The invention discloses a method for synthesizing trans-cyclohexanedimethanamine, comprising steps of reacting cyclohexene oxide and methylamine aqueous solution under the catalysis of boric acid, and then adding sulfuric acid, dewatering to form an ester, ring-closing under alkaline conditions, adding methylamine aqueous solution and boric acid for hermetic reaction, and distilling to obtain trans-cyclohexanedimethanamine. The synthetic process is simple to perform, provides facilitated isolation and purification and high yield and product purity, and is suitable for batch production.

Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis

A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with >99% enantiomeric excess (ee) by sequential use of (R)- and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.

HYDRONOPOL DERIVATIVES AS AGONISTS ON HUMAN ORL1 RECEPTORS

The invention relates to a group of hydronopol derivatives which are agonists on human ORL1 (nociceptin) receptors. The invention also relates to the preparation of these compounds, to pharmaceutical compositions containing a pharmacologically active amount of at least one of these novel hydronopol derivatives as an active ingredient, as well as to the use of these pharmaceutical compositions for the treatment of disorders in which ORL1 receptors are involved. The invention relates to compounds of the general formula (1) wherein the symbols have the meanings as given in the description.

Synthesis, pharmacological and biophysical characterization, and membrane-interaction QSAR analysis of cationic amphiphilic model compounds

Cationic amphiphilic drugs have a propensity to interact with biological interphases. This study was designed to gain more insight into the molecular properties of catamphiphilic drugs which govern this type of interaction. A series of phenylpropylamine model compounds were synthesized in which modifications were incorporated at the aromatic part of the molecule. The replacement of 45Ca2+ from phosphatidylserine monolayers served to monitor drug binding to the phospholipid. The influence on the phase- transition temperature of liposomes of dipalmitoylphosphatidic acid was measured to assess the perturbing action of the drugs on the structural organization of phospholipid assemblies. The antiarrhythmic activity of the compounds was determined in Langendorff preparations of guinea pig hearts to assess the membrane-stabilizing action. Quantitative structure-activity relationship (QSAR) models for these endpoints were developed using both intra- and intermolecular QSAR descriptors. Intermolecular membrane- interaction descriptors were derived from molecular dynamics simulations of the compounds in a model phospholipid monolayer. QSAR models were derived for all endpoints using partial least-squares regression (PLS) and a genetic algorithm tool, the genetic function approximation (GFA). Membrane- interaction descriptors appear to be of a particular importance in explaining the influence of the compounds on the phase-transition temperature of DPPA liposomes, while the other endpoints can be adequately modeled by intramolecular descriptors. The calcium-displacing activity at phosphatidylserine monolayers is governed by the electrostatic properties of the compounds. Measures of lipophilicity and molecular size are of particular importance for antiarrhythmic activity. Possible improvements to both the molecular modeling and the applied computational protocol of membrane-solute systems are identified and discussed.

Enzymatic resolution of (±)-2-(N(β)-t-butoxycarbonyl-N(α)- methylhydrazino)cycloalkanols

Racemates of cis- and trans-2-(N(β)-t-butoxycarbonyl-N(α)- methylhydrazino)cyclopentanols and -cyclohexanols 1-4 were resolved through lipase PS- or Novozym 435-catalysed asymmetric acylation of the secondary OH group at the (R)-stereogenic centre. High e

Substituted trans-1,2-diaminocyclohexyl amide compounds

Substituted trans-1,2-diaminocyclohexyl amide compounds demonstrating selective opioid receptor binding possess utility as analgesic, diuretic, and psychotherapeutic agents. A method of preparing the compounds, pharmaceutical compositions employing the compounds, and a method of alleviating pain employing the compounds are also disclosed.

SUBSTITUTED NAPHTHALENYLOXY-1,2-DIAMINOCYCLOHEXYL AMIDE COMPOUNDS

Substituted naphthalenyloxy-or naphthalenylthiooxyamides of trans-1,2-diaminocyclohexanes possess selective kappa opioid receptor site binding activity and are thus useful as analgesic or diuretic agents. Methods of preparing the compounds, pharmaceutical compositions, and a method for their use as analgesic agents are also disclosed.

O.N-Bis(diphenylphosphino) Derivatives of Chiral trans- and cis-2-Aminocyclohexanols: Synthesis and Enantioselective Behaviour as Ligands in Rh-based Homogeneous Hydrogenation Catalysts

trans- and cis-2-Methylamino cyclohexanols (MAC) were prepared in enantiomerically pure forms and transformed into O.N-bis(diphenylphosphino) derivatives ("PONP").An analogous trans-1R;2R-aminocyclohexanol PONP could only be isolated in an impure form, whereas the attempted synthesis of PONP's of diastereomeric trans-2-(N-α-phenylethylamino)-cyclohexanols failed.Cationic Rh(I)-chelates of the new PONP's catalyzed the enantioselective hydrogenation of dehydro-α-acylamino acids with /= 97percent ee.A comparison of the enantiodiscriminating properties of the MAC-PONP's with structurally related chiral ligands leads to surprising conclusions.

Substituted trans-1,2-diaminocyclohexyl amide compounds

Substituted trans-1,2-diaminocyclohexyl amide compounds demonstrating selective opioid receptor binding possess utility as analgesic, diuretic, and psychotherapeutic agents. A method of preparing the compounds, pharmaceutical compositions employing the co