cis-α,β-Diphenyl-butyrolacton

Base Information

• Chemical Name: cis-α,β-Diphenyl-butyrolacton
• CAS No.: 133908-45-9
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.286
• Mol file: 133908-45-9.mol

Synonyms:cis-α,β-Diphenyl-butyrolacton

Chemical Property of cis-α,β-Diphenyl-butyrolacton

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-α,β-Diphenyl-butyrolacton

There total 3 articles about cis-α,β-Diphenyl-butyrolacton 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:

phenylethyl 2-diazo-2-phenylacetate → cis-α,β-Diphenyl-butyrolacton (133908-45-9,5635-42-7)

Guidance literature:

With C₁₀₈H₅₂F₁₂N₄O₁₂Rh₂S₈; In dichloromethane; for 2.5h; stereoselective reaction; Reflux;

DOI:10.1021/acscatal.0c03689

Reference yield:

phenylacetic acid (103-82-2) + (dimethylamino)phenyl-(2-phenylvinyl)oxosulfonium fluoroborate → (3S,4R)-3,4-diphenyldihydrofuran-2(3H)-one (5635-42-7) + cis-α,β-Diphenyl-butyrolacton (133908-45-9,5635-42-7) + C16H14O2 (5635-42-7)

Guidance literature:

phenylacetic acid; With n-butyllithium; N¹,N³-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

(dimethylamino)phenyl-(2-phenylvinyl)oxosulfonium fluoroborate; In tetrahydrofuran; hexane; at -78 - -25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.6b02622

Reference yield:

phenylacetic acid (103-82-2) + (-)-(S)-(dimethylamino)phenyl(trans-2-phenylethenyl)oxosulfonium fluoroborate (36471-09-7) → (3S,4R)-3,4-diphenyldihydrofuran-2(3H)-one (5635-42-7) + cis-α,β-Diphenyl-butyrolacton (133908-45-9,5635-42-7) + C16H14O2 (5635-42-7)

Guidance literature:

phenylacetic acid; With n-butyllithium; N¹,N³-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

(-)-(S)-(dimethylamino)phenyl(trans-2-phenylethenyl)oxosulfonium fluoroborate; In tetrahydrofuran; hexane; at -78 - -25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.6b02622

upstream raw materials:

phenylacetic acid

(-)-(S)-(dimethylamino)phenyl(trans-2-phenylethenyl)oxosulfonium fluoroborate

Downstream raw materials:

3,4-diphenyldihydrofuran-2(3H)-one

Refernces

• 1、 Peraino, Nicholas J.,Kaster, Sven H.,Wheeler, Kraig A.,Kerrigan, Nessan J.. "Asymmetric Synthesis of γ-Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts". . p. 606 - 615. Retrieved 2017/04/26.