5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene

Base Information

• Chemical Name: 5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene
• CAS No.: 1417801-95-6
• Molecular Formula: C₃₆H₃₈O₆S
• Molecular Weight: 598.76
• Mol file: 1417801-95-6.mol

Synonyms:5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene

Chemical Property of 5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene

There total 22 articles about 5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene 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: 68.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)propyl)phenyl)-9,10-dihydrophenanthrene (1417801-89-8) → 5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene (1417801-95-6)

Guidance literature:

5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)propyl)phenyl)-9,10-dihydrophenanthrene; With diethyl chlorophosphate; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

formaldehyd; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1002/anie.201406621

Reference yield:

2-(4-methoxy-2-(3-(phenylsulfonyl)propyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1417801-88-7) → 5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene (1417801-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate; water; potassium bromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 36 h / 65 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.33 h / -78 °C / Inert atmosphere

2.3: 0.33 h / -78 - 0 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; water; potassium carbonate; potassium bromide; lithium diisopropyl amide; In tetrahydrofuran; toluene; 2.1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/ol303390a

Reference yield:

5'-(benzyloxy)-2-isopropoxy-3,4'-dimethoxy-2',6-divinyl-1,1'-biphenyl (1417801-87-6) → 5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthrene (1417801-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 22 h / 50 °C / Inert atmosphere

2.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 24 h / 31029.7 Torr / Inert atmosphere

3.1: pyridine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

4.1: potassium carbonate; water; potassium bromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 36 h / 65 °C / Inert atmosphere

5.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

5.2: 0.33 h / -78 °C / Inert atmosphere

5.3: 0.33 h / -78 - 0 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 5%-palladium/activated carbon; water; hydrogen; potassium carbonate; potassium bromide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 1.1: |Diels-Alder Cycloaddition / 5.1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/ol303390a

upstream raw materials:

5'-(benzyloxy)-2-isopropoxy-3,4'-dimethoxy-2',6-divinyl-1,1'-biphenyl

2-(4-methoxy-2-(3-(phenylsulfonyl)propyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

formaldehyd

5-isopropoxy-2,6-dimethoxy-3-(4-methoxy-2-(3-(phenylsulfonyl)propyl)phenyl)-9,10-dihydrophenanthrene

Downstream raw materials:

4-((3,7-dimethoxy-6-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthren-4-yl)oxy)-2H-pyran-2-one

3,7-dimethoxy-6-(4-methoxy-2-(3-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthren-4-ol

Refernces

• 1、 Zhao, Peng,Beaudry, Christopher M.. "Total synthesis of (±)-cavicularin: Control of pyrone diels-alder regiochemistry using isomeric vinyl sulfones". . p. 402 - 405. Retrieved 2013/03/13.