13575-72-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Aminoindan-1-ol is used as a chiral building block for the synthesis of various biologically active molecules, contributing to the development of new pharmaceuticals.
Used in Neurodegenerative Disease Treatment:
2-Aminoindan-1-ol is studied for its potential neuroprotective properties, which may be beneficial in the treatment of neurodegenerative diseases.

InChI:InChI=1/C9H11NO/c10-8-5-6-3-1-2-4-7(6)9(8)11/h1-4,8-9,11H,5,10H2

Upstream product

• 2338-18-3 2-aminoindane hydrochloride 
• 171285-94-2 (1R,2R)-2-azido-2,3-dihydro-1H-inden-1-yl-4-nitrobenzoate 
• 15028-10-1 indan-1,2-dione-2-oxime 
• 29365-64-8 (1R,2R)-(-)-2-phthalimidoindan-1-ol 
• 74036-09-2 2-(1-oxo-indan-2-yl)-isoindole-1,3-dione 
• 83-33-0 inden-1-one 
• 1775-27-5 2-bromoindanone 
• 26536-31-2 indano<1,2-b>aziridine 
• 26976-63-6 2-amino-1-indanone 
• 13943-70-9 2-nitro-2,3-dihydro-1H-inden-1-one 
• 95-13-6 1-indene 
• 13575-94-5 2-(acetylamino)-1-indanone 
• 13575-71-8 trans-2-Acetamidoindanol-⁽¹⁾ 
• 166942-30-9 (1S,2R)-2-azido-2,3-dihydro-1H-inden1-ol 

Downstream Products

• 94077-02-8 (1R,2R)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-indan-1-ol 
• 144285-04-1 (1R,2R)-2-(2-hydroxybenzylideneamino)-1-indanol 
• 23672-01-7 (-)-(1R,2R)-2-benzylaminoindan-1-ol 
• 94077-17-5 (1R,2R)-2-(3-Methoxy-benzylamino)-indan-1-ol 
• 94077-19-7 (1R,2R)-2-(2,3-Dimethoxy-benzylamino)-indan-1-ol 
• 23672-01-7 (+/-)-trans-2-Benzylamino-indanol-⁽¹⁾ 
• 13575-72-9 (1R,2R)-trans-2-amino-1-indanol 
• 144285-04-1 (1S,2S)-2-(2-hydroxybenzylideneamino)-1-indanol 
• 94077-04-0 (1R,2R)-2-{[1-(2,3-Dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-indan-1-ol 
• 94077-03-9 (1R,2R)-2-{[1-(3-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-indan-1-ol 

Relevant academic research and scientific papers

Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation

(±)-cis-2-amino-1-indanol was diastereoselectively synthesized from 1,2-indanedion-2-oxime in ethanol at 25 °C under 10% Pd/C-catalyzed hydrogenation conditions. Under the same hydrogenation condition, 1,2-indanedion-2-oxime and their derivatives having one and/or two electron-donating groups in aliphatic or aromatic part of indanyl ring were diastereoselectively reduced to racemic cis-2-amino-1-indanol derivatives. From 1,2-indanedion-1-oxime, (±)-trans-1-amino-2-indanol was obtained in ethanol at 25 °C over a 10% Pd/BaSO4 catalyst. In contrast, the 10% Pd/BaSO4-catalyzed hydrogenation reaction in ethanol at 45 °C afforded cis-1-hydroxyamino-2-indanol from 1,2-indanedion-1-oxime, followed by reduction to form (±)-cis-1-amino-2-indanol. The diastereoselectivity of β-aminoindanols was dependent on the Pd catalyst, reaction temperature, and pH of the reaction medium.

Efficient preparation of biologically important 1,2-amino alcohols

An efficient three-step methodology developed for the preparation of 1,2-amino alcohols. In the first step a rapid coupling between bromoketones and potassium phthalimide in ionic liquid produced-phthalimido ketones in quantitative yields, which is followed by a facile reduction using NaCNBH 3 in acetic acid to give corresponding phthalimido alcohols and finally effecting hydrazinolysis in water at 60C to yield biologically important 1,2-amino alcohols.

Cyclic trans-β-amino alcohols: Preparation and enzymatic kinetic resolution

Enantioenriched cyclic β-amino alcohols, trans-2-aminocyclohexanols (ee, >99%), trans-2-aminocyclopentanols (ee, >99%), trans-1-amino-2- indanols (ee, >99%) and trans-2-amino-1-indanols (ee, ～98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution.

Enzymatic hydroxylation by dopamine β-hydroxylase

The three-dimensional aspects of the chemistry of dopamine β-hydroxylase (DBH) was studied through a conformationally-restricted substrate analog approach. We found that the DBH-catalyzed hydroxylation of 2-aminoindane (1) exclusively produced the trans-(1S,2S)-2-amino-1-indanol (4S) (93% ee) in contrast to the stereochemical course of the pro-R hydroxylation of the DBH/phenethylamine reaction. Studies with stereospecifically deuterium labeled 2-aminoindanes 2 and 3 show that the production of (1S)-aminoindanol 4S is the result of stereospecific pro-S hydrogen abstraction followed by the oxygen binding with overall retention of configuration. On the basis of these findings, we propose a model for the interaction of the phenethylamine substrates with the enzyme.

Stereoselective synthesis of 1,2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers

Asymmetric reduction of α-oxoketoxime ethers with the reagents prepared in situ from trimethyl borate and chiral amino alcohols derived from either L-proline or α-pinene was investigated. Both cyclic and acyclic α- oxoketoxime ethers were reduced to afford the corresponding chiral 1,2amino alcohols with high enantioselectivities.

Synthese de 2,3,4,4a,9,9a-Hexahydro-11-indenopyrazines, Analogues Rigides de 3-Methyl-2-phenylpiperazines et Antidepresseurs Potentiels

The synthesis of various diastereoisomeric (+/-) trans-(VIII) and cis-2,3,4,4a,9,9a-hexahydro-1H-indenopyrazines (IX) is described, using as key step for piperazine ring formation an alkoxyphosphonium salt.Compound VIIIa was prepared as a potential serotonin reuptake inhibitor.

Synthesis of Enantiomerically Pure cis and trans-2-Amino-1-indanol

Enantiomerically pure cis and trans-2-amino-1-indanols 1 and 2 were synthesized via a highly enetioslective lipase catalyzed transestrification of racemic cis-2-azido-1-indanol 3.

COPPER(II) IN ORGANIC SYNTHESIS. X. THE IMPORTANCE OF STERIC HINDRANCE IN THE DESIGN OF CHIRAL TRIDENTATE LIGAND COPPER(II) CATALYSTS FOR ENANTIOSELECTIVE MICHAEL REACTIONS

Several copper(II) complexes with tridentate chiral ligands derived from 2-substituted 2-aminoethanols have been tested as catalysts for enantioselective Michael reactions.The degree of enantioselection increases with the increase of the steric hindrance of the substituents and the best result (65percent e.e.) was obtained with the benzyl-substituted catalyst.A comparison of these results with those obtained with complexes derived from 2-amino-1-indanols gives useful information about the requirements for the optimization of the catalyst design.