37414-44-1

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indene-2-carboxaldehyde,2,3-dihydrois used as a key intermediate in the synthesis of selective calpain inhibitors. Calpains are a family of calcium-activated cysteine proteases that play a crucial role in various cellular processes, including cell signaling, apoptosis, and cytoskeletal remodeling. Inhibition of calpains has been implicated in the treatment of several diseases, such as neurodegenerative disorders, muscular dystrophy, and cancer.
The development of selective calpain inhibitors is essential for targeting specific calpain isoforms and minimizing off-target effects. 1H-Indene-2-carboxaldehyde,2,3-dihydroserves as a valuable building block in the design and synthesis of such inhibitors, contributing to the advancement of therapeutic agents for various medical conditions.

Upstream product

• 201230-82-2 carbon monoxide 
• 95-13-6 1-indene 
• 2461-35-0 2,3-epoxy-1,2,3,4-tetrahydronaphthalene 
• 60-29-7 diethyl ether 

Downstream Products

• 582299-17-0 2-hydroxy-2-(indan-2-yl)-1-phenylethan-1-one 
• 582299-01-2 1-(2,3-dihydro-1H-inden-2-yl)-2-oxo-2-phenylethyl 4-methylbenzene-1-sulfonate 
• 251655-63-7 [4-(5-ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-(2-indanylmethyl)amine 
• 181227-46-3 (2R)-amino(2,3-dihydro-1H-inden-2-yl)ethanoic acid 
• 4254-32-4 indan-2-carboxylic acid methyl ester 
• 1083335-65-2 C₁₉H₂₀O 
• 251655-64-8 [4-(5-Cyano-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-(2-indanylmethyl)amine 

Relevant academic research and scientific papers

Efficient platinum(II) catalyzed hydroformylation reaction in water: Unusual product distribution in micellar media

The hydroformylation of a variety of terminal and internal alkenes is efficiently performed by cationic platinum triflate complexes of the type [P2Pt(H2O)2](OTf)2 under mild conditions in an aqueous micellar medium. The use of surfactants is essential to ensure dissolution of the catalyst and substrate in water with catalysts being positioned on the anionic surface of the micelles. Aldehydes are obtained with linear to branched ratios up to >99:1. With styrene derivatives also the corresponding benzaldehydes are formed. The catalyst can be separated by extraction of the organic products with hexane and recycled for at least four times with only a modest loss of activity and no effect on selectivity.

Highly enantioselective hydroformylation of aryl alkenes with diazaphospholane ligands

(Chemical Equation Presented) Asymmetric, rhodium-catalyzed hydroformylation of terminal and internal aryl alkenes with diazaphospholane ligands is reported. Under partially optimized reaction conditions, high enantioselectivity (>90% ee) and regioselectivities (up to 65:1 α:β) are obtained for most substrates. For terminal alkenes, both enantioselectivity and regioselectivity are proportional to the carbon monoxide partial pressure, but independent of hydrogen pressure. Hydroformylation of para-substituted styrene derivatives gives the highest regioselectivity for substrates bearing electron-withdrawing substituents. A Hammett analysis produces a positive linear correlation for regioselectivity.

Phosphine oxides as ligands in the hydroformylation reaction

A new rhodium-phosphine oxide system has been investigated in the hydroformylation reaction. Some of the phosphine oxide ligands of type 2-12 (i.e. R2N(CH2)nP(O)R′2, R′ = Ph, Cy; n = 0, 1, 2, 3; R = Me, Et, iPr, or NR2 = 2-pyridyl) were found to be better ligands than the phosphine analogues (i.e. R2N(CH)2PR′2) in the hydroformylation of olefins catalyzed by rhodium complexes. Detailed examination of factors controlling the selectivity for aldehydes formation revealed the following characteristics of the reaction: (a) use of ligands having bulkier amino groups decrease the yield of the aldehydes slightly; (b) ligands having amino groups with low basicity decrease the rate of the hydroformylation dramatically; (c) the electronic properties of the phosphine oxide group have no influence on the hydroformylation reaction; (d) uncoordinating solvents of low polarity such as dichloromethane, chloroform and toluene gave the best reaction rate and selectivity; (e) spectroscopic investigation of the hydroformylation of styrene catalyzed by rhodium with ligand 2 shows that the ligand is coordinated by the amino and the phosphine oxide groups under 1 atm of CO-H2 and only by the amino group under 600 lbf in-2 of CO-H2.

Asymmetric Hydroformylation of 1,2-Disubstituted Olefins Catalysed by Chiral Phosphinephosphite-Rhodium(I) Complexes

Hydroformylations of internal olefins such as (E)- and (Z)-but-2-ene, (E)- and (Z)-1-phenylprop-1-ene, indene, and 1,2-dihydronaphthalene catalysed by (R,S)-binaphos-RhI complex phosphite> or its enantiomer gave the corresponding oxoaldehydes in up to 97percent enantiomeric excess, e.e.