4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline

Base Information

• Chemical Name: 4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline
• CAS No.: 88176-88-9
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 88176-88-9.mol

Synonyms:4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline

Chemical Property of 4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline

There total 12 articles about 4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline 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: 40.0%

3a-(3,4-dimethoxyphenyl)-5,5-(ethylenedioxy)-3,3a,4,5,6,7-hexahydro-2H-inden-2-one N-methylnitrone (91713-15-4) → 4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline (88176-88-9)

Guidance literature:

With p-toluenesulfonyl chloride; In pyridine; water; for 1h; Ambient temperature;

DOI:10.1021/jo00194a026

Reference yield: 40.0%

C20H25NO5 (88176-87-8) → 4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline (88176-88-9)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; In water;

DOI:10.1016/S0040-4039(00)86218-8

Reference yield:

3-Ethoxycyclohex-2-en-1-one (5323-87-5) → 4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline (88176-88-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) n-BuLi, 2) glacial acetic acid, 10percent aq. HCl / 1a) ether/hexane, -60 deg C, 1 h, 1b) RT, overnight

2: pyridinium p-toluenesulfonate / benzene / 120 h / Heating

3: 1) B₂H₆, 2) 3N NaOH, 30 percent H₂O₂ / 1) THF, RT, overnight, 2a) 45 deg C, 5 h, 2b) RT

4: sodium acetate, pyridinium chlorochromate / CH₂Cl₂

5: 1) NaH / 1) DME, 3 h, RT, 2a) RT, overnight, 2b) 3 h, reflux

6: NaIO₄/KMnO₄/K₂CO₃ / dioxane; H₂O / 48 h / Ambient temperature

7: 1N KOH / ethanol / 2 h / Heating

8: 100 percent / sodium acetate / ethanol / 40 h / Heating

9: 40 percent / p-toluenesulfonyl chloride / pyridine; H₂O / 1 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydroxide; potassium permanganate; sodium periodate; n-butyllithium; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; acetic acid; p-toluenesulfonyl chloride; pyridinium chlorochromate; diborane; In 1,4-dioxane; pyridine; ethanol; dichloromethane; water; benzene;

DOI:10.1021/jo00194a026

upstream raw materials:

C₂₀H₂₅NO₅

3a-(3,4-dimethoxyphenyl)-5,5-(ethylenedioxy)-3,3a,4,5,6,7-hexahydro-2H-inden-2-one N-methylnitrone

3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one

3-Ethoxycyclohex-2-en-1-one

Downstream raw materials:

cis-4a-(3,4-dimethoxyphenyl)-2-methyl-6-oxo-3,4,4a,5,6,7,8,8a-octahydroisoquinolinium perchlorate

4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-2,3,4,4a,5,6,7,8-octahydroisoquinoline

Refernces

• 1、 McMurry, John E.,Farina, Vittorio. "TOTAL SYNTHESIS OF O-METHYLPALLIDININE". . p. 4653 - 4656. Retrieved 2007/10/02.