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
• Article Data: 7

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

General Description

The chemical (1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol is a compound with the molecular formula C9H11NO. It is a chiral molecule, containing both an amine group and a hydroxyl group. Its IUPAC name is (1S,2R)-2-Amino-1,2-dihydro-1H-inden-1-ol. (1S,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol has potential applications in pharmaceutical and medicinal chemistry, particularly in the development of new drugs and therapeutic agents. Its unique structure and functional groups make it a valuable building block for the synthesis of organic molecules with biological activity. Further research into its properties and potential uses could lead to new discoveries in the field of drug development and medicinal chemistry.

Upstream product

• 13575-72-9 2-amino-1-indanol 
• 171482-71-6 (1R,2R)-2-azido-2,3-dihydro-1H-inden-1-ol 
• 2338-18-3 2-aminoindane hydrochloride 
• 166942-30-9 (1S,2R)-2-azido-2,3-dihydro-1H-inden1-ol 
• 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 

Downstream Products

• 94077-09-5 (-)-(2RS,4R,5S)-2-phenyl-3,3a,4,8b-tetrahydro-2H-indeno<2,1-d>oxazole 
• 94077-02-8 (1R,2R)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-indan-1-ol 
• 144285-04-1 (1S,2R)-2-(2-hydroxybenzylideneamino)-1-indanol 
• 144285-04-1 (1R,2R)-2-(2-hydroxybenzylideneamino)-1-indanol 
• 94077-03-9 (1R,2R)-2-{[1-(3-Methoxy-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 
• 23672-01-7 (-)-(1S,2R)-2-benzylaminoindan-1-ol 
• 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 

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.

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.