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

Description

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

Uses

Used in Pharmaceutical Applications:
(1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol is used as a building block in the synthesis of various compounds for pharmaceutical applications. Its chiral nature allows for the development of enantiomerically pure drugs, which can have different biological activities and reduce potential side effects.
Used in Asymmetric Catalysis:
(1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol is used as a chiral ligand in asymmetric catalysis, a technique used to produce enantiomerically pure compounds. Its unique molecular properties make it a valuable tool in the development of new catalysts and synthetic methods.
Used in Drug Development Research:
(1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol is used in research for the development of new drugs and materials. Its molecular properties and chiral nature make it a promising candidate for the study of novel therapeutic agents and the advancement of drug discovery techniques.

Upstream product

• 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 
• 15028-10-1 indan-1,2-dione-2-oxime 
• 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 
• 2338-18-3 2-aminoindane hydrochloride 
• 171482-71-6 (1R,2R)-2-azido-2,3-dihydro-1H-inden-1-ol 
• 13575-72-9 2-amino-1-indanol 

Downstream Products

• 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 
• 94077-02-8 (1R,2R)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-indan-1-ol 

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.