(S)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one

Base Information

• Chemical Name: (S)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one
• CAS No.: 1402739-94-9
• Molecular Formula: C₂₀H₂₀O₂
• Molecular Weight: 292.378
• Mol file: 1402739-94-9.mol

Synonyms:

Chemical Property of (S)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one

There total 8 articles about (S)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one 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:

7-methyl-2,2-diphenyl-5,6-octadien-1-ol (906542-62-9) → (S)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one (1402739-94-9) + (R)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one

Guidance literature:

With C₁₂H₁₇O₅^(1-)*Ag⁽¹⁺⁾; In dichloromethane; at 23 ℃; for 2h; Overall yield = 96 %; enantioselective reaction;

DOI:10.1002/chem.201200547

Reference yield:

6-methyl-2,2-diphenylhepta-4,5-dienoic acid (1402739-99-4) → (S)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one (1402739-94-9) + (R)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one

Guidance literature:

With 2C₅₀H₅₆O₄P^(1-)*C₇₄H₁₀₄Au₂O₆P₂⁽²⁺⁾; In water; at 20 ℃; for 19h; Solvent; Overall yield = 97 %; Overall yield = 29 mg; enantioselective reaction; Darkness;

DOI:10.1002/anie.201404729

Reference yield:

t-butyldimethyl[(4-methyl-4-((tetrahydro-2H-pyran-2-yl)oxy)pent-2-yn-1-yl)]silane → (S)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one (1402739-94-9) + (R)-5-(2-methylprop-1-en-1-yl)-3,3-diphenyldihydrofuran-2(3H)-one

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 20 °C

2.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

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

3.2: 3 h / 0 - 20 °C / Inert atmosphere

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

4.2: 7 h / -78 - 20 °C / Inert atmosphere

5.1: potassium hydroxide / water; ethanol / 6 h / 75 °C

6.1: 2C₅₀H₅₆O₄P^(1-)*C₇₄H₁₀₄Au₂O₆P₂⁽²⁺⁾ / water / 19 h / 20 °C / Darkness

With pyridine; dmap; lithium aluminium tetrahydride; 2C₅₀H₅₆O₄P^(1-)*C₇₄H₁₀₄Au₂O₆P₂⁽²⁺⁾; tetrabutyl ammonium fluoride; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1002/anie.201404729

upstream raw materials:

7-methyl-2,2-diphenyl-5,6-octadien-1-ol

4-methyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]pent-2-yn-1-ol

4-methylpenta-2,3-dien-1-ol

4-methylpenta-2,3-dien-1-yl-benzoate