469898-63-3

Upstream product

• 621-59-0 isovanillin 
• 18075-40-6 O-allylisovanillin 
• 18075-41-7 2-allyl-3-hydroxy-4-methoxybenzaldehyde 
• 75-16-1 methylmagnesium bromide 
• 92345-90-9 3,4-dimethoxy-2-allylbenzaldehyde 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 30836-91-0 1-Methyl-5,6-dihydroisochinolin 
• 469898-43-9 (R)-3,4-dimethoxy-1-(1'-hydroxyethyl)-2-(prop-1''-enyl)benzene 
• 469898-55-3 3',4'-dimethoxy -2'-(1-propenyl)acetophenone 
• 469898-40-6 1-(2-allyl-3,4-dimethoxy-phenyl)-ethanone 

Relevant academic research and scientific papers

CuI Mediated One-Pot Cycloacetalization/Ketalization of o-Carbonyl Allylbenzenes: Synthesis of Benzobicyclo[3.2.1]octane Core

CuI/DMSO-mediated intramolecular cycloacetalization/ketalization of o-carbonyl allylbenzenes has been achieved for constructing [6,6,5]-tricycles having a ketal motif in good yields. The expeditious one-step route provides a three C-O bond formation. The key products with the structural framework of a benzofused dioxabicyclo[3.2.1]octane core have been confirmed by X-ray crystallographic analysis. Synthesis of dihydroisocoumarin has been studied.

Bi(OTf)3-Mediated Intramolecular Olefinic Cyclization: Synthesis of Substituted Aryl-Dihydronaphthalenes and Indenes

In this article, a facile two-step and one-pot synthetic route for the preparation of substituted aryl dihydronaphthalenes starting from 2-allylbenzaldehydes via Grignard 1,2-addition and Bi(OTf)3-catalyzed intramolecular olefinic cyclization has been developed. A five-membered ring indene skeleton is also prepared via olefin isomerization, 1,2-addition followed by cyclization. Some key structures are determined using single-crystal X-ray crystallography. A possible mechanism is presented herein.

One-pot access to 2-naphthols and benzofurans via the aerobic Wacker-type oxidation/intramolecular aldol cyclization

An aerobic Wacker-type oxidation/intramolecular aldol cyclization synthetic route toward two oxygenated 2-naphthols 3 and benzofurans 4 starting with skeleton 2 with good yields is described. The route has been carried by the one-pot transformation of the regioselective PdCl2/CuCl 2-mediated Wacker oxidative cyclization of skeleton 2 with molecular oxygen under the alkaline methanolic condition. Skeleton 2 was prepared from skeleton 1 in moderate total yields via the known protocol.

Facile synthesis of substituted isoquinolines

A facile three-step protocol toward methoxy isoquinolines 7 starting with substituted 2-allylbenzaldehydes 9 was described. The overall synthetic process of skeleton 7 was carried out using the Grignard addition, PCC-oxidation, and one-pot oxidative cleavage of the olefinic group of skeleton 9 with OsO 4-NaIO4 followed by the condensation of the resulting 1,5-dicarbonyl compounds with NH4OAc. Skeleton 9 was prepared in high yield via the known Claisen rearrangement of skeleton 8 and O-methylation. Papaverine 2 is also synthesized via the simple three-step synthetic protocol.

Synthesis of tetrahydroanthracen-9-ones by the domino aldol condensation/Diels-Alder cycloaddition

A facile protocol toward several substituted 3-aryl-3,4,4a,10-tetrahydro- 2H-anthracen-9-ones 1 starting with substituted 2-allylbenzaldehydes 2 was described. The overall synthetic process was carried out by the domino aldol condensation/Diels-Alder cycloaddition of skeleton 2 with substituted cinnamaldehydes 3 in an alkalic aqueous-methanolic solution followed by base-induced double migration of the resulting cycloadducts. Skeleton 2 was prepared from isovanillin (4) in moderate yield in five-steps via the known procedures with the synthetic sequence of O-allylation, Claisen rearrangement, O-methylation, Grignard methylation, and PCC-mediated oxidation.

The synthesis of R-3-alkoxy-1-(1′-hydroxyethyl)-4-methoxy-2-(1″-propenyl)benzenes utilizing Corey-Bakshi-Shibata asymmetric reductions

Pyrolysis of the 3-O-allyl derivative 7 of isovanillin followed by alkylation of the derived allylphenol 8 afforded a series of benzaldehyde derivatives 9-11 each of which was transformed by initial treatment with methylmagnesium bromide followed by oxida

Towards the synthesis of chiral isochromanquinones. The use of Corey-Bakshi-Shibata reductions

(1R,3R,4S)-3,4-Dihydro-4-hydroxy-6-methoxy-1,3-dimethylisochroman-5,8-dione has been synthesized in 65% ee from (1R,3R,4S)-5-benzyloxy-3,4-dihydro-4-hydroxy-6-methoxy-1,3-dimethylisochroman by catalytic hydrogenolysis followed by Fremy's salt oxidation of