(4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one

Base Information

Chemical Name:(4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one
CAS No.:791822-00-9
Molecular Formula:C₁₇H₂₁NO₃
Molecular Weight:287.359
Hs Code.:

Synonyms:(4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one

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Chemical Property of (4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one

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Technology Process of (4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one

There total 8 articles about (4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

: 791821-98-2
(R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

: 791822-00-9
(4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one

: 791822-03-2
(4S,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one

Guidance literature:: (R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 24h; Further stages.;
DOI:10.1016/j.tet.2004.06.145

Reference yield:

: 6380-23-0
3,4-dimethoxystyrene

: 791822-00-9
(4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1.65 g / [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxyphenyl) / CH₂Cl₂ / 14 h / Heating

2.1: CF₃CO₂H / CH₂Cl₂ / 1 h / 0 °C

2.2: 45 percent / DBU / CH₂Cl₂ / 24 h / 20 °C

With [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxyphenyl); trifluoroacetic acid; In dichloromethane; 2.2: intramolecular Michael reaction;
DOI:10.1016/j.tet.2004.06.145

Reference yield:

: (1S,4R)-4-But-3-enylamino-cyclopent-2-enol

: 791822-00-9
(4R,10R)-4-(3,4-dimethoxyphenyl)-1,3,4,6,7,10-hexahydroquinolizin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 3.05 g / Et₃N / methanol / 4 h / 70 °C

2.1: 99 percent / imidazole / dimethylformamide / 50 h / 20 °C

3.1: 98 percent / ethylene; Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 57 h / 20 °C

4.1: 96 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 1.65 g / [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxyphenyl) / CH₂Cl₂ / 14 h / Heating

7.1: CF₃CO₂H / CH₂Cl₂ / 1 h / 0 °C

7.2: 45 percent / DBU / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; Grubbs catalyst first generation; ethene; [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxyphenyl); tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Dess-Martin oxidation / 7.2: intramolecular Michael reaction;
DOI:10.1016/j.tet.2004.06.145