13306-86-0

Basic information

• Product Name: 2-(4-methoxybenzyl)-2,3-dihydro-1H-inden-1-one
• Synonyms: 2-(4-methoxybenzyl)-2,3-dihydro-1H-inden-1-one
• CAS NO: 13306-86-0
• Molecular Weight: 252.313
• Mol File: 13306-86-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2-(4-methoxybenzyl)-2,3-dihydro-1H-inden-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methoxybenzyl)-2,3-dihydro-1H-inden-1-one(13306-86-0)
• EPA Substance Registry System: 2-(4-methoxybenzyl)-2,3-dihydro-1H-inden-1-one(13306-86-0)

Safety Data

• Hazardous Substances Data: 13306-86-0(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 83-33-0 inden-1-one 
• 62708-42-3 o-allylbenzaldehyde 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 105-13-5 4-Methoxybenzyl alcohol 
• 609-67-6 2-Iodobenzoyl chloride 
• 88-67-5 2-Iodobenzoic acid 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5706-14-9 2-[(E)-4-methoxyphenylmethylidene]-1-indanone 
• 2393-23-9 4-methoxy-benzylamine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 372510-69-5 ethyl 2-allylbenzoate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 61463-59-0 2-allyl benzoic acid methyl ester 

Downstream Products

• 1214734-32-3 C₁₇H₁₈O₂ 

Relevant articles and documents

Iridium-catalyzed chemoselective transfer hydrogenation of α, β-unsaturated ketones to saturated ketones in water

A chemoselective iridium-catalyzed transfer hydrogenation of α, β-unsaturated ketones was realized in water. The C[dbnd]C double bonds of 2-benzylidene indanones and analogues were hydrogenated exclusively catalyzed by an iridium complex (0.1 mol%) bearin

Scope and Mechanism of the Redox-Active 1,2-Benzoquinone Enabled Ruthenium-Catalyzed Deaminative α-Alkylation of Ketones with Amines

The catalytic system formed in situ from the reaction of a cationic Ru-H complex with 3,4,5,6-tetrachloro-1,2-benzoquinone was found to mediate a regioselective deaminative coupling reaction of ketones with amines to form the α-alkylated ketone products. Both benzylic and aliphatic primary amines were found to be suitable substrates for the coupling reaction with ketones in forming the α-alkylated ketone products. The coupling reaction of PhCOCD3 with 4-methoxybenzylamine showed an extensive H/D exchange on both α-CH2 (41% D) and β-CH2 (21%) positions on the alkylation product. The Hammett plot obtained from the reaction of acetophenone with para-substituted benzylamines p-X-C6H4CH2NH2 (X = OMe, Me, H, F, Cl, CF3) showed a strong promotional effect by the amine substrates with electron-releasing groups (ρ = -0.49 ± 0.1). The most significant carbon isotope effect was observed on the α-carbon of the alkylation product (Cα = 1.020) from the coupling reaction of acetophenone with 4-methoxybenzylamine. The kinetics of the alkylation reaction from an isolated imine substrate led to the empirical rate law: rate = k[Ru][imine]. A catalytically active Ru-catecholate complex was synthesized from the reaction of the cationic Ru-H complex with 3,5-di-tert-butyl-1,2-benzoquinone and PCy3. The DFT computational study was performed on the alkylation reaction, which revealed a stepwise mechanism of the [1,3]-carbon migration step via the formation of a Ru(IV)-alkyl species with a moderate energy of activation (ΔG? = 32-42 kcal/mol). A plausible mechanism of the catalytic alkylation reaction via an intramolecular [1,3]-alkyl migration of an Ru-enamine intermediate has been compiled on the basis of these experimental and computational data.

Nickel-catalyzed: Exo -selective hydroacylation/Suzuki cross-coupling reaction

The first nickel-catalyzed intramolecular hydroacylation/Suzuki cross coupling cascade of o-allylbenzaldehydes with a broad range of phenylboronic acid neopentyl glycol esters has been developed. This strategy shows high regioselectivity and step economy in the construction of two C-C bonds via aldehyde C-H bond activation, affording valuable indanones with high efficiency.