94077-46-0

Basic information

• Product Name: (1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol
• Synonyms: (1S,2R)-2-Amino-1-indanol;(1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol
• CAS NO: 94077-46-0
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149
• Mol File: 94077-46-0.mol

Chemical Properties

• Boiling Point: 297℃
• Flash Point: 133℃
• Appearance: /
• Density: 1.212
• CAS DataBase Reference: (1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol(94077-46-0)
• EPA Substance Registry System: (1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol(94077-46-0)

Safety Data

• Hazardous Substances Data: 94077-46-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol is utilized as a key building block for the synthesis of organic molecules with biological activity. Its unique structure and functional groups make it instrumental in creating new drugs and therapeutic agents that can address various medical conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol serves as a valuable compound for studying the properties and potential uses of chiral molecules. Its presence in research could lead to the discovery of novel drug candidates and contribute to the development of more effective treatment options.

Upstream product

• 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 
• 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

• 94077-19-7 (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 
• 94077-04-0 (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 
• 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 
• 23672-01-7 (-)-(1S,2R)-2-benzylaminoindan-1-ol 
• 144285-04-1 (1S,2R)-2-(2-hydroxybenzylideneamino)-1-indanol 
• 94077-09-5 (-)-(2RS,4R,5S)-2-phenyl-3,3a,4,8b-tetrahydro-2H-indeno<2,1-d>oxazole 

Relevant articles and documents

Practical Synthetic Procedures for the Iron-Catalyzed Intermolecular Olefin Aminohydroxylation Using Functionalized Hydroxylamines

A set of practical synthetic procedures for the iron-catalyzed intermolecular olefin aminohydroxylation reactions in gram scale is reported. In these transformations, a bench-stable functionalized hydroxylamine is applied as the amination reagent. This method is compatible with a broad range of synthetically valuable olefins including those that are incompatible with the existing aminohydroxylation methods. It also provides valuable amino alcohol building blocks with regio- and stereochemical arrays that are complementary to known methods.

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.

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.

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.

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.

CATALYTIC ENANTIOSELECTIVE DIELS-ALDER REACTIONS USING TITANIUM COMPLEXES OF CIS-N-SULFONYL-2-AMINO-1-INDANOLS

A titanium complex derived from (1R,2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-1-indanol catalyzes the Diels-Alder reaction of 2-bromoacrolein and cyclopentadiene with 96.5:3.5 enantioselectivity.A new and efficient synthesis of 2-amino-1-indanol (6)

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.