(R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene

Base Information

• Chemical Name: (R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene
• CAS No.: 158732-44-6
• Molecular Formula: C₁₉H₂₂O₄
• Molecular Weight: 314.381
• Mol file: 158732-44-6.mol

Synonyms:(R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene

Chemical Property of (R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene

There total 3 articles about (R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene 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:

(E)-3-phenylpropenal (14371-10-9) + Trimethyl-(4-methylene-1,5-dioxa-spiro[5.5]undec-2-en-2-yloxy)-silane (158732-42-4) → (R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene (158732-44-6)

Guidance literature:

With monoacylated tartaric acid-borane complex (CAB complex-6b); In tetrahydrofuran; dichloromethane; at -98 ℃; for 1h;

DOI:10.1248/cpb.42.839

Reference yield:

3-phenyl-propenal (104-55-2) + Trimethyl-(4-methylene-1,5-dioxa-spiro[5.5]undec-2-en-2-yloxy)-silane (158732-42-4) → (R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene (158732-44-6) + 4-((E)-(S)-2-Hydroxy-4-phenyl-but-3-enyl)-1,5-dioxa-spiro[5.5]undec-3-en-2-one

Guidance literature:

With titanium(IV) isopropylate; 3 A molecular sieve; (R)-1,1'-Bi-2-naphthol; In tetrahydrofuran; at -78 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(00)00259-7

Reference yield:

4-methyl-1,5-dioxaspiro[5.5]undec-3-en-2-one (4412-03-7) → (R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene (158732-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / n-BuLi, diisopropylamine / tetrahydrofuran / 2 h / -78 °C

2: monoacylated tartaric acid-borane complex (CAB complex-6b) / tetrahydrofuran; CH₂Cl₂ / 1 h / -98 °C

With n-butyllithium; monoacylated tartaric acid-borane complex (CAB complex-6b); diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.42.839

upstream raw materials:

(E)-3-phenylpropenal

Trimethyl-(4-methylene-1,5-dioxa-spiro[5.5]undec-2-en-2-yloxy)-silane

3-phenyl-propenal

4-methyl-1,5-dioxaspiro[5.5]undec-3-en-2-one

Downstream raw materials:

methyl (R,E)-5-(tert-butyldimethylsilyloxy)-3-oxo-7-phenylhept-6-enoate

(4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one

(4R,6R,1'E)-4-hydroxy-6-(2'-phenylvinyl)-3,4,5,6-tetrahydro-2H-pyran-2-one

(R)-goniothalamin