25501-32-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-(+)-1-Indanol is used as a building block for the synthesis of pharmaceutical compounds, particularly for the development of orally bioavailable GPR40 agonists. One such example is DS-1558, which is used to stimulate insulin secretion. The compound's unique structure and chirality make it a valuable component in the design and synthesis of novel drugs targeting specific receptors.

InChI:InChI=1/C9H10O/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4,9-10H,5-6H2/t9-/m0/s1

Upstream product

• 108-22-5 Isopropenyl acetate 
• 6351-10-6 1-Indanol 
• 100465-50-7 <1,1'-Binaphthalene>-2,2'-diol dibutanoate 
• 68567-23-7 (S)-(-)-2,3-dihydro-1H-inden-yl acetate 
• 124040-95-5 <1,1'-Binaphthalene>-2,2'-diol butanoate 
• 5177-66-2 1-ethoxyvinyl acetate 
• 123-20-6 vinyl n-butyrate 
• 57-10-3 1-hexadecylcarboxylic acid 
• 876-27-7 4-chlorophenyl acetate 
• 92799-73-0 1-indanyl hydroperoxide 
• 63318-61-6 α-Aethoxyacrylsaeuremethylester 
• 108-05-4 vinyl acetate 
• 330825-79-1 (1S,2R)-1-methyl-2-formylindan 
• 496-11-7 INDANE 

Downstream Products

• 175288-46-7 [2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-isopropyl-carbamic acid (S)-indan-1-yl ester 
• 83-33-0 inden-1-one 
• 256237-45-3 (S)-N,N-diisopropyl O-(indan-1-yl)carbamate 
• 415975-55-2 (2S,2R')-(3,4-dichlorophenyl)(tetrahydropyran-2-yl)acetic acid indanyl ester 
• 415975-56-3 (2R,2S')-(3,4-dichlorophenyl)(tetrahydropyran-2-yl)acetic acid indanyl ester 
• 666824-82-4 triethyl (1R)-2,3-dihydro-1H-inden-1-ylmethanetricarboxylate 
• 907562-44-1 (S)-2-((S)-Indan-1-yloxycarbonylamino)-hexanoic acid methyl ester 
• 6351-10-6 1-Indanol 
• 854001-42-6 (S)-2-((S)-Indan-1-yloxycarbonylamino)-hexanoic acid 
• 854001-46-0 {(S)-1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pentyl}-carbamic acid (S)-indan-1-yl ester 

Relevant academic research and scientific papers

Asymmetric transfer hydrogenation of ketonic substrates catalyzed by (η5-C5Me5)MCl complexes (M = Rh and Ir) of (1S, 2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine

The rhodium and iridium (η5-C5Me5)MCl complexes (3a: M = Rh; 3b: M = Ir) of (1S,25)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine were found to be catalyst precursors for asymmetric transfer hydrogenation of acetophenone, 2-acetonaphthone, 1-tetralone, and 1-indanone to give (S)-1-phenylethanol (90% ee), (S)-1-(2-naphthyl)ethanol (85% ee), (S)-1-tetralol (97% ee), and (S)-indanol (99% ee), respectively.

Asymmetric Aggregative Activation. A New Useful Concept for Asymmetric Reduction

Reduction of arylketones with a Complex Reducing Agent containing 2 equivalents of Zn0 and 4 equivalents of sodium chiraldate in a mixture of THF and methylcyclohexane for 1 equivalent of arylketone took place with a chiral induction from 56 to 89 percent of enantiomeric excess.

Designer Outer Membrane Protein Facilitates Uptake of Decoy Molecules into a Cytochrome P450BM3-Based Whole-Cell Biocatalyst

We report an OmpF loop deletion mutant, which improves the cellular uptake of external additives into an Escherichia coli whole-cell biocatalyst. Through co-expression of the OmpF mutant with wild-type P450BM3 in the presence of decoy molecules, the yield

Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity

A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction.

Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71

Enantiopure benzo-fused cyclic alcohols have been used as a building block of a drug for Parkinson’s disease. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of seven lactic acid bacteria (LAB) strains were investigated as whole-cell biocatalyst in the enantioselective reduction of 1-indanone (1). Lactobacillus paracasei BD71 was found to have the best reductive capacity. Effects of different parameters such as pH, incubation time, agitation speed and temperature, on enantiomeric excess (ee) and conversion were investigated in a bioconversion. (S)-1-indanol ((S)-2) could be used as precursor for the synthesis of rasagiline mesylate TVP1012 for the therapy of Parkinson’s illness. It was produced in gram-scale (5.24 g), high yield (93%) and enantiomerically pure form using L. paracasei BD71 whole-cell biocatalysts. Also, to our knowledge, this is the first report on production of (S)-2 using whole-cell catalyst in enantiopure form, excellent yield, conversion and gram scale. This is a cheap, clean and eco-friendly process for production of (S)-2 compared to chemical processes.

Supramolecular chiral electrochemical reduction of acetophenone with hybridization of a chiral multifarene and Au nanoparticles

A supramolecular chiral electrode was constructed by layer-by-layer assembly of gold nanoparticles (AuNPs) and an S-chiral multifarene [3,2,1] (S-CMF) on the surface of a glassy carbon electrode, which was applied for the electroreduction of acetophenone. The host-guest encapsulation of the substrate within the chiral cavity was confirmed by 1H NMR, fluorescence titration, and molecular simulation. The composite on the electrode surface was characterized by electrochemical impedance spectroscopy (EIS) and transmission electron microscopy (TEM). Optimization of the electrolysis process was performed to give a high yield of 70.9% and high enantioselectivity of 63.9% ee, which exhibited superior reactivity to the previously reported materials. The repeatability of the experiment was tested via five separate experiments and indicated consistent stability, recyclability, and reusability of the novel chiral electrode. The proposed mechanism involved supramolecular encapsulation, two single-electron transfer steps, and proton addition. The chiral electroorganic reduction was extended to more substrates to provide successful yields and enantioselectivity.

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.

Homochiral Dodecanuclear Lanthanide "cage in Cage" for Enantioselective Separation

It is extremely difficult to anticipate the structure and the stereochemistry of a complex, particularly when the ligand is flexible and the metal node adopts diverse coordination numbers. When trivalent lanthanides (LnIII) and enantiopure amino acid ligands are utilized as building blocks, self-assembly sometimes yields rare chiral polynuclear structures. In this study, an enantiopure carboxyl-functionalized amino acid-based ligand with C3 symmetry reacts with lanthanum cations to give a homochiral porous coordination cage, (Δ/λ)12-PCC-57. The dodecanuclear lanthanide cage has an unprecedented octahedral "cage-in-cage"framework. During the self-assembly, the chirality is transferred from the enantiopure ligand and fixed by the binuclear lanthanide cluster to give 12 metal centers that have either Δor λ homochiral stereochemistry. The cage exhibits excellent enantioselective separation of racemic alcohols, 2,3-dihydroquinazolinones, and multiple commercially available drugs. This finding exhibits a rare example of a multinuclear lanthanide complex with a dual-walled topology and homochirality. The highly ordered self-assembly and self-sorting of flexible amino acids and lanthanides shed light on the chiral transformation between different complicated artificial systems that mimic natural enzymes.

Chiral salen - Ni (II) based spherical porous silica as platform for asymmetric transfer hydrogenation reaction and synthesis of potent drug intermediate montekulast

Heterogeneous catalyst has an edge over homogeneous systems in terms of recyclability, activity, stability and recovery. Silica has evolved as a good support material in heterogeneous systems due to its stability and ability to get modified as per the end application. Herein, we report a novel chiral Ni-Schiff base derived catalyst and its immobilization into mesoporous silica which was synthesized by post-grafting process. The chiral catalyst demonstrated remarkably high catalytic activity, enantioselectivity (up to 99 % enantiomers excess) for heterogeneous asymmetric transfer hydrogenation of various ketones. The developed catalyst was characterized by Ultraviolet-visible spectroscopy (UV–vis), Fourier-Transform Infrared spectroscopy (FT-IR), X-ray Powder Diffraction (XRD), Brunauer-Emmett-Teller (BET isotherm), Scanning Electron Microscopy – Energy Dispersive X-ray Spectroscopy (SEM-EDX), High Resolution – Transmission Electron Microscopy (HR-TEM), Vibrating Sample Magnetometer (VSM), X-ray Photoelectron Spectroscopy (XPS) and elemental analysis. The catalyst could be recovered and reused for multiple consecutive runs without losing the enantioselectivity. The chiral catalyst was used in asymmetric transfer hydrogenation reaction for synthesizing enantiomerically pure drug intermediate Montekulast.

Enantioselective direct, base-free hydrogenation of ketones by a manganese amido complex of a homochiral, unsymmetrical P-N-P′ ligand

The use of manganese in homogeneous hydrogenation catalysis has been a recent focus in the pursuit of more environmentally benign base metal catalysts. It has great promise with its unique reactivity when coupled with metal-ligand cooperation of aminophosphine pincer ligands. Here, a manganese precatalyst Mn(P-N-P′)(CO)2, where P-N-P′ is the amido form of the ligand (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2, has been synthesized and used for base-free ketone hydrogenation. This catalyst shows exceptionally high enantioselectivity and good activity, with tolerance for base-sensitive substrates. NMR structural analysis of intermediates formed by the reaction of the amido complex with hydrogen under pressure identified a reactive hydride with an NOE contact with the syn amine proton. Computational analysis of the catalytic cycle reveals that the heterolytic splitting of dihydrogen across the MnN bond in the amido complex has a low barrier while the hydride transfer to the ketone is the turnover-limiting step. The pro-S transition state is found to be usually much lower in energy than the pro-R transition state depending on the ketone structure, consistent with the high (S) enantiomeric excess in the alcohol products. The energy to reach the transition state is higher for the distortion of the in-coming ketone than that of the hydride complex. In a one-to-one comparison with the similar iron catalyst FeH2(CO)(P-NH-P′), the manganese catalyst is found to have higher enantioselectivity, often over 95% ee, while the iron catalyst has higher activity and productivity. An explanation of these differences is provided on the basis of the more deformable iron hydride complex due to the smaller hydride ligands.