68000-22-6

Basic information

• Product Name: 1H-Indene-1-carboxylic acid, 2,3-dihydro-, (S)-
• Synonyms: (S)-Indan-1-carboxylic acid;(+)-indane-1-carboxylic acid;(S)-(-)-1-indancarboxylic acid;(S)-1-indancarboxylic acid;(-)-(S)-1-indancarboxylic acid;(S)-Indan-1-carbonsaeure
• CAS NO: 68000-22-6
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Mol File: 68000-22-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Indene-1-carboxylic acid, 2,3-dihydro-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indene-1-carboxylic acid, 2,3-dihydro-, (S)-(68000-22-6)
• EPA Substance Registry System: 1H-Indene-1-carboxylic acid, 2,3-dihydro-, (S)-(68000-22-6)

Safety Data

• Hazardous Substances Data: 68000-22-6(Hazardous Substances Data)

Usage

Chiral molecule

contains a stereocenter
The molecule has a central carbon atom bonded to four different groups, making it asymmetric.

(S)-configuration

counterclockwise arrangement of substituents
The (S) designation indicates that the substituents around the stereocenter are arranged in a counterclockwise manner when following the CIP priority rules.

Carboxylic acid derivative

1H-Indene-1-carboxylic acid, 2,3-dihydro-
The compound is derived from 2,3-dihydro-1H-indene by introducing a carboxylic acid functional group.

Potential applications

pharmaceutical industry
Due to its unique structure and properties, the compound may be used in drug development and other pharmaceutical applications.

Synthesis

other organic compounds
The compound can be used as a starting material or intermediate in the synthesis of other organic compounds.

Stereochemistry

enantiomerically pure drugs and biologically active molecules
The chiral nature of the compound makes it an important starting material for the production of enantiomerically pure drugs and other biologically active molecules.

Upstream product

• 256531-66-5 (S)-1-Diisopropylcarbamoyloxy-indan-1-carboxylic acid methyl ester 
• 14209-41-7 3H-indene-1-carboxylic acid 
• 26452-96-0 methyl indane-1-carboxylate 
• 36330-15-1 methyl (S)-2,3-dihydro-1H-indene-3-carboxylate 
• 67-56-1 methanol 
• 14381-42-1 Indan-1-carboxylic acid 
• 697-64-3 (R)-indan-1-ol 
• 46292-93-7 R-(+)-phenylsuccinic acid 
• 118-10-5 Cinchonin 

Relevant articles and documents

Chiral benzyllithium compounds: High configurative stability of (R)- and (S)-1-lithioindan-1-yl N,N-diisopropylcarbamate and unexpected stereochemical course of the substitution reactions

The title compound, 6, was generated by stereospecific deprotonation of the optically active carbamate 5 with sec-butyllithium/TMEDA and proved to be configuratively completely stable in ethereal solution at -78 °C. Compared with open-chain analogs, the trend for stereoretentive substitution is enhanced. Even the reaction with trialkyltin chlorides leads to partial racemization due to competing front face attack. Semiempirical calculations point to an increased degree of pyramidalization and to a higher barrier for planarization in the cyclic benzyllithium compound, both of which disfavor the rear face attack.

Dynamic enzymatic kinetic resolution of methyl 2,3-dihydro-1h-indene-1- carboxylate

A new reaction setup for kinetic enzymatic resolution was established and is demonstrated for the case of the hydrolase-catalysed conversion of methyl 2,3-dihydro-1H-indene1-carboxylate (1) in conjunction with a base-catalysed racemisation. The system allows controlled racemisation, resulting in efficient dynamic kinetic resolution (DKR) of the title compound. Short reaction times and high enantio-selectivities were obtained with CAL-B and TBD (1,5,7-triazabicyclo[4,4.0]dec-5-ene). Compound (R)-1 (ee 95%) served as a starting material in a domino reaction that led to the biaryl indanyl ketone (R)-8, a lead compound for novel inhibitors of peptidyl-prolyl-cis/irans- isomerases, in 94 % ee. Wiley-VCH Verlag GmbH & Co. KGaA,.

On the Absolute Configuration of (+)-Indane-1-carboxylic Acid

The (R)-configuration, attributed to (+)-indane-carboxylic acid ((+)-1) by Fredga, is unequivocally confirmed (Scheme 1).Configurational doubts, raised by an erroneous ORD. curve of (-)-1-methylindane ((-)-4) published by Brewster and Buta, are unfounded (cf. the following paper of Brewster and the corrections in ).This was further verified by preparing deuteriated 1-methylindanes starting with (-)-(R)-3-phenylbutyric acid ((-)-(R)-5) as well as with (+)-(R)-1 or (-)-(S)-1 (Scheme 2).The ORD. curves of the optically active 4 thus obtained were (disregarding deuterium isotope effects) identical or antipodal, respectively (cf.Fig.1,2, and 7a-e).Optically active methyl indane-1-carboxylates ((-)-(R)-14 or (+)-(S)--14) show a strong solvent dependence of their ORD. and CD. spectra with a sign inversion occuring in going from isooctane to methanol or benzene.The observed changes can be explained by a change in the population of comformations where the ester carbonyl group is eclipsed either with the C(1),C(2)- or C(1),H-bond, with the n,?*-transition having a slightly different energy and the ester group an essentially enantiomeric environment with respect to its orientation relative to the benzene moiety.