(6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-3-ol

Base Information

• Chemical Name: (6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-3-ol
• CAS No.: 82644-36-8
• Molecular Formula: C18H19NO3
• Molecular Weight: 297.3484
• Mol file: 82644-36-8.mol

Synonyms:

Chemical Property of (6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-3-ol

Chemical Property:

• Vapor Pressure: 7.31E-10mmHg at 25°C
• Boiling Point: 480.6°C at 760 mmHg
• Flash Point: 244.5°C
• Density: 1.237g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-3-ol

There total 9 articles about (6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-3-ol 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:

(R)-1,2-dimethoxy-5,6,6a,7-tetrahydro-6-p-toluenesulfonyl-4H-dibenzo[de,g]quinolin-3-ol (1359071-18-3) → (R)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-3-ol (82644-36-8)

Guidance literature:

With sodium naphthalenide; In 1,2-dimethoxyethane; Cooling with isopropanol-dry ice; Inert atmosphere;

DOI:10.1016/j.tet.2011.12.022

Reference yield:

2-(benzyloxy)-3,4-dimethoxy-1-(2-methoxyvinyl)benzene → (R)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-3-ol (82644-36-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogenchloride / water; acetone / 1 h / 0 - 20 °C / Inert atmosphere

2.1: titanium(IV) tetraethanolate / dichloromethane / 4 h / Reflux; Inert atmosphere

3.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 18 h / -78 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: hydrogenchloride / 1,2-dimethoxyethane; water / 1 h / 80 °C

7.1: chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / N,N-dimethyl acetamide / 1 h / 110 °C / Inert atmosphere

7.2: 20 °C / Inert atmosphere

8.1: sodium naphthalenide / 1,2-dimethoxyethane / Cooling with isopropanol-dry ice; Inert atmosphere

With hydrogenchloride; titanium(IV) tetraethanolate; sodium tetrahydroborate; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); boron trifluoride diethyl etherate; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; sodium naphthalenide; In methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl acetamide; water; acetone;

DOI:10.1016/j.tet.2011.12.022

Reference yield:

(R)-N-[2-(2-(benzyloxy)-3,4-dimethoxyphenyl)ethylidene]-p-toluenesulfinamide → (R)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-3-ol (82644-36-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 18 h / -78 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: hydrogenchloride / 1,2-dimethoxyethane; water / 1 h / 80 °C

5.1: chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate / N,N-dimethyl acetamide / 1 h / 110 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: sodium naphthalenide / 1,2-dimethoxyethane / Cooling with isopropanol-dry ice; Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); boron trifluoride diethyl etherate; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; sodium naphthalenide; In methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl acetamide; water;

DOI:10.1016/j.tet.2011.12.022

upstream raw materials:

(R)-N-[2-(2-(benzyloxy)-3,4-dimethoxyphenyl)ethyl]-p-toluenesulfinamide

(+)-1-(2-bromobenzyl)-5-benzyloxy-6,7-dimethoxy-2-p-toluenesulfinyl-1,2,3,4-tetrahydroisoquinoline

(R)-1-(2-bromobenzyl)-5-benzyloxy-6,7-dimethoxy-2-p-toluenesulfonyl-1,2,3,4-tetrahydroisoquinoline

(R)-1-(2-bromobenzyl)-6,7-dimethoxy-2-p-toluenesulfonyl-1,2,3,4-tetrahydroisoquinolin-5-ol

Downstream raw materials:

3-Hydroxynuciferin

lirinine