(R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene

Base Information

• Chemical Name: (R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene
• CAS No.: 1579249-94-7
• Molecular Formula: C₁₉H₂₀O
• Molecular Weight: 264.367
• Mol file: 1579249-94-7.mol

Synonyms:(R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene

Chemical Property of (R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene

There total 4 articles about (R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene 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: 83.0%

diethyl (E)-2-(3,4-dihydronaphthalen-1(2H)-ylidene)ethyl phosphate (1579250-10-4) + 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane (213596-33-9) → (R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene (1579249-94-7)

Guidance literature:

2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane; With 1-((1S,2S)-2-hydroxyindan-1-yl)-3-pentamethylphenylimidazolinium hexafluorophosphate; sodium methylate; copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

diethyl (E)-2-(3,4-dihydronaphthalen-1(2H)-ylidene)ethyl phosphate; In tetrahydrofuran; at 20 ℃; for 60h; enantioselective reaction;

DOI:10.1021/jo500068p

Reference yield:

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → (R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene (1579249-94-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 0 °C

1.2: 24 h / 20 °C

2.1: diisobutylaluminium hydride / hexane; toluene / 12 h / -78 - 20 °C

3.1: dmap; triethylamine / dichloromethane / 20 h / 0 - 20 °C

4.1: 1-((1S,2S)-2-hydroxyindan-1-yl)-3-pentamethylphenylimidazolinium hexafluorophosphate; copper(l) chloride; sodium methylate / tetrahydrofuran / 0.08 h / 20 °C

4.2: 60 h / 20 °C

With dmap; 1-((1S,2S)-2-hydroxyindan-1-yl)-3-pentamethylphenylimidazolinium hexafluorophosphate; sodium methylate; sodium hydride; diisobutylaluminium hydride; triethylamine; copper(l) chloride; In tetrahydrofuran; hexane; dichloromethane; toluene; mineral oil;

DOI:10.1021/jo500068p

Reference yield:

2-(1,2,3,4-tetrahydronaphthalen-1-yl)ethanol (68480-12-6) → (R)-1-ethenyl-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene (1579249-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 20 h / 0 - 20 °C

2.1: 1-((1S,2S)-2-hydroxyindan-1-yl)-3-pentamethylphenylimidazolinium hexafluorophosphate; copper(l) chloride; sodium methylate / tetrahydrofuran / 0.08 h / 20 °C

2.2: 60 h / 20 °C

With dmap; 1-((1S,2S)-2-hydroxyindan-1-yl)-3-pentamethylphenylimidazolinium hexafluorophosphate; sodium methylate; triethylamine; copper(l) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo500068p

upstream raw materials:

3,4-dihydronaphthalene-1(2H)-one

diethyl (E)-2-(3,4-dihydronaphthalen-1(2H)-ylidene)ethyl phosphate

2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane

2-(1,2,3,4-tetrahydronaphthalen-1-yl)ethanol

Downstream raw materials:

(R)-2-(1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)ethanol

Refernces