94077-01-7

Basic information

• Product Name: (1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol
• Synonyms: (1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol
• CAS NO: 94077-01-7
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149
• Mol File: 94077-01-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 297℃
• Flash Point: 133℃
• Appearance: /
• Density: 1.212
• PKA: 13.85±0.40(Predicted)
• CAS DataBase Reference: (1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol(94077-01-7)
• EPA Substance Registry System: (1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol(94077-01-7)

Safety Data

• Hazardous Substances Data: 94077-01-7(Hazardous Substances Data)

Usage

General Description

(1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol is a chemical compound with the molecular formula C9H11NO. It is an amino alcohol that is derived from indene, a bicyclic aromatic hydrocarbon. (1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol is chiral, and its (1R,2R) enantiomer is the biologically active form. It has been studied for its potential pharmaceutical applications, including as a building block in the synthesis of various compounds. It has also been investigated for its potential as a chiral ligand in asymmetric catalysis. (1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol has molecular properties that make it of interest to researchers studying the development of new drugs and materials.

Upstream product

• 13575-72-9 2-amino-1-indanol 
• 2338-18-3 2-aminoindane hydrochloride 
• 1775-27-5 2-bromoindanone 
• 83-33-0 inden-1-one 
• 74036-09-2 2-(1-oxo-indan-2-yl)-isoindole-1,3-dione 
• 29365-64-8 (1R,2R)-(-)-2-phthalimidoindan-1-ol 
• 171285-94-2 (1R,2R)-2-azido-2,3-dihydro-1H-inden-1-yl-4-nitrobenzoate 
• 166942-30-9 (1S,2R)-2-azido-2,3-dihydro-1H-inden1-ol 
• 171482-71-6 (1R,2R)-2-azido-2,3-dihydro-1H-inden-1-ol 
• 15028-10-1 indan-1,2-dione-2-oxime 

Downstream Products

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

Relevant articles and documents

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.

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.