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126456-43-7

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  • (1S,2R)-(-)-cis-1-Amino-2-indanol CAS 126456-43-7 In stock (1S,2R)-(-)-cis-1-Amino-2-hydroxyindane

    Cas No: 126456-43-7

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126456-43-7 Usage

Description

(1S,2R)-(-)-cis-1-Amino-2-indanol is a white to light yellow crystal powder that serves as a key intermediate in the synthesis of various pharmaceutical compounds. It is a main constituent of indinavir, a potent HIV (human immunodeficiency virus) protease inhibitor, and is also used in the preparation of other heterocyclic compounds with antiviral properties.

Uses

Used in Pharmaceutical Industry:
(1S,2R)-(-)-cis-1-Amino-2-indanol is used as a reagent in the synthesis of heterocyclic compounds that act as integrase inhibiting antiviral agents. It plays a crucial role in the production of HIV protease inhibitors, such as Indinavir (I525000), which are essential in the treatment of HIV/AIDS.
Used in Catalyst Production:
(1S,2R)-(-)-cis-1-Amino-2-indanol is utilized in the preparation of oxazaborolidine catalysts. These catalysts are capable of catalyzing the asymmetric reduction of aromatic ketones with high enantioselectivity, which is vital for the synthesis of enantiomerically pure compounds in various chemical and pharmaceutical applications.
Used in the Synthesis of (-)-1,2,5,6-Tetrahydropyridine:
(1S,2R)-(-)-cis-1-Amino-2-indanol may be used to prepare (-)-1,2,5,6-tetrahydropyridine by reacting with methyl (E,E)-4-oxo-2-[(2,6,6-trimethylcyclohex-1-enyl)vinylbut-2-enoate. (1S,2R)-(-)-cis-1-Amino-2-indanol has potential applications in various chemical and pharmaceutical processes.
Used in the Synthesis of (RS,1S,2R)-(-)-2,4,6-Trimethylbenzenesulfinic Acid 1-(2,4,6-Trimethylbenzenesulfonylamino)indan-2-yl Ester:
(1S,2R)-(-)-cis-1-Amino-2-indanol is also used in the synthesis of (RS,1S,2R)-(-)-2,4,6-trimethylbenzenesulfinic acid 1-(2,4,6-trimethylbenzenesulfonylamino)indan-2-yl ester, which may have potential applications in various chemical and pharmaceutical processes.

Reaction

Ligand component used in the chromium-catalyzed highly selective asymmetric ene reactions between aryl aldehydes and alkoxy- and silyloxyalkenes. Ligand component for the chromium-catalyzed highly enantioselective o inverse-demand hetero-Diels-Alder reactions of α,β-unsaturated aldehydes. Ligand component for the magnesium-catalyzed conjugate addition reaction of 1,3-dicarbonyl compounds to nitroalkenes. Component for stereoselective asymmetric 6π-azaelectrocyclization through the reaction between the (E)-3- carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-1-amino-2-indanol derivatives. Ligand component for palladium-catalzyed asymmetric azaelectrocyclization for the preparation of 2,4- disubstituted chiral 1,2,5,6-tetrahydropyridines. Component for organocatalytic conjugate addition of formaldehyde N,N-dialkylhydrazones to β,γ -Unsaturated α-keto esters. N-Sulfinyl urea organocatalyst component for enantioselective aza-henry reaction. Component for organocatalytic enantioselective additions of indoles to nitroalkenes.

Check Digit Verification of cas no

The CAS Registry Mumber 126456-43-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,6,4,5 and 6 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 126456-43:
(8*1)+(7*2)+(6*6)+(5*4)+(4*5)+(3*6)+(2*4)+(1*3)=127
127 % 10 = 7
So 126456-43-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H11NO/c10-9-7-4-2-1-3-6(7)5-8(9)11/h1-4,8-9,11H,5,10H2/p+1/t8-,9+/m1/s1

126456-43-7 Well-known Company Product Price

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  • TCI America

  • (A1624)  (1S,2R)-(-)-1-Amino-2-indanol  >98.0%(GC)(T)

  • 126456-43-7

  • 1g

  • 370.00CNY

  • Detail
  • TCI America

  • (A1624)  (1S,2R)-(-)-1-Amino-2-indanol  >98.0%(GC)(T)

  • 126456-43-7

  • 5g

  • 1,130.00CNY

  • Detail
  • Alfa Aesar

  • (H32066)  (1S,2R)-(-)-cis-1-Amino-2-indanol, 97%   

  • 126456-43-7

  • 1g

  • 667.0CNY

  • Detail
  • Alfa Aesar

  • (H32066)  (1S,2R)-(-)-cis-1-Amino-2-indanol, 97%   

  • 126456-43-7

  • 5g

  • 2300.0CNY

  • Detail
  • Alfa Aesar

  • (H32066)  (1S,2R)-(-)-cis-1-Amino-2-indanol, 97%   

  • 126456-43-7

  • 25g

  • 8613.0CNY

  • Detail
  • Aldrich

  • (440833)  (1S,2R)-(−)-cis-1-Amino-2-indanol  99%

  • 126456-43-7

  • 440833-1G

  • 603.72CNY

  • Detail
  • Aldrich

  • (440833)  (1S,2R)-(−)-cis-1-Amino-2-indanol  99%

  • 126456-43-7

  • 440833-5G

  • 2,098.98CNY

  • Detail
  • Aldrich

  • (440833)  (1S,2R)-(−)-cis-1-Amino-2-indanol  99%

  • 126456-43-7

  • 440833-25G

  • 7,751.25CNY

  • Detail

126456-43-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (1S,2R)-(-)-1-Amino-2-indanol

1.2 Other means of identification

Product number -
Other names 3aR

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:126456-43-7 SDS

126456-43-7Downstream Products

126456-43-7Relevant articles and documents

Manganese catalyzed asymmetric oxidation of alkanes to optically active ketones bearing asymmetric center at the α- position

Komiya, Naruyoshi,Noji, Satoru,Murahashi, Shun-Ichi

, p. 7921 - 7924 (1998)

Chiral (salen)manganese(III) complex catalyzed oxidation of symmetrical alkanes with iodosylbenzene gives the corresponding optically active ketones (up to 70% ee). The optically active 2-hydroxy-1-indanone (7) thus obtained is a versatile precursor of cis-1-amino-2-indanol (8) which is a key intermediate of chiral auxiliary and anti HIV protease inhibitor (9).

Stereoselective dioxygenase-catalysed benzylic hydroxylation at prochiral methylene groups in the chemoenzymatic synthesis of enantiopure vicinal aminoindanols

Boyd, Derek R.,Sharma, Narain D.,Bowers, Nigel I.,Goodrich, Peter A.,Groocock, Melanie R.,Blacker, A.John,Clarke, David A.,Howard, Tina,Dalton, Howard

, p. 1559 - 1562 (1996)

Enantiopure benzylic alcohols containing two stereogenic centres in a cis- relationship result from stereoselective monohydroxylation of achiral 2- substituted indans in cultures of Pseudomonas putida UV4 and are used in the chemoenzymatic synthesis of both cis- and trans-aminoindanol enantiomers.

Lipase-mediated resolution of inden-1-ol

Takahashi,Koike,Ogasawara

, p. 1585 - 1587 (1995)

Optically pure inden-1-ol has been obtained efficiently in both enantiomeric forms via kinetic deacylation of racemic 1-acetoxyindene using lipase PS.

A practical synthesis of (1S,2R)-1-amino-2-indanol, a key component of an HIV protease inhibitor, indinavir

Kajiro, Hiroshi,Mitamura, Shuichi,Mori, Atsunori,Hiyama, Tamejiro

, p. 1093 - 1100 (1999)

A synthesis of (1S,2R)-1-amino-2-indanol (1), a key component of an HIV protease inhibitor, was accomplished through (R)-2-hydroxy-1-indanone ((R)- 3), which was prepared by an intramolecular Friedel-Crafts acylation of (R)2- acetoxy-3-phenylpropanoic acid readily available from D-(R)-phenylalanine. Alternatively, (R)-3 was obtained by an enzymatic resolution of (±)-2- acetoxy-1-indanone. Ketone (R)-3 was convened into 1 through an oxime formation and diastereoselective hydrogenation.

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

Nguyen, Thi Ha,Ma, Eunsook

supporting information, p. 3717 - 3728 (2021/11/01)

(±)-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.

Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions

Fang, Yuanding,Fu, Kang,Shi, Lei,Zhao, Rong,Zhou, Jia

supporting information, p. 20682 - 20690 (2020/09/07)

The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.

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