syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene

Base Information

• Chemical Name: syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene
• CAS No.: 166804-07-5
• Molecular Formula: C₂₇H₃₂O₃Si
• Molecular Weight: 432.635
• Mol file: 166804-07-5.mol

Synonyms:syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene

Chemical Property of syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene

There total 2 articles about syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene 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: 62.0%

allyl 4-(3-((tert-butyldimethylsilyl)oxy)phenyl)<4.4.1>propella-2,8-diene-11-carboxylate → syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene (166804-07-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; a) from 60 deg C to 70 deg C, 41 h, b) reflux, 24 h;

DOI:10.1021/ja00102a020

Reference yield:

4-(3-((tert-butyldimethylsilyl)oxy)phenyl)<4.4.1>propella-2,8-diene-11-carboxylic acid (142566-67-4) → syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene (166804-07-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / Cs₂CO₃ / acetonitrile / 26 h

2: 62 percent / DDQ / dioxane / a) from 60 deg C to 70 deg C, 41 h, b) reflux, 24 h

With caesium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; acetonitrile;

DOI:10.1021/ja00102a020

Reference yield: 97.0%

syn-11-((allyloxy)carbonyl)-3-(3-((tert-butyldimethylsilyl)oxy)phenyl)-1,6-methano<10>annulene (166804-07-5) → syn-11-((allyloxy)carbonyl)-3-(3-hydroxyphenyl)-1,6-methano<10>annulene (166804-08-6)

Guidance literature:

With potassium fluoride; hydrogen bromide; In N,N-dimethyl-formamide; for 45h;

DOI:10.1021/ja00102a020

upstream raw materials:

4-(3-((tert-butyldimethylsilyl)oxy)phenyl)<4.4.1>propella-2,8-diene-11-carboxylic acid

Downstream raw materials:

syn-11-((allyloxy)carbonyl)-3-(3-hydroxyphenyl)-1,6-methano<10>annulene

syn-11-carboxy-3-(3-(propyloxy)phenyl)-1,6-methano<10>annulene

syn-11-((allyloxy)carbonyl)-3-(3-(propyloxy)phenyl)-1,6-methano<10>annulene