4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-, (2S)-

Base Information

• Chemical Name: 4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-, (2S)-
• CAS No.: 190835-53-1
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• Mol file: 190835-53-1.mol

Synonyms:

Chemical Property of 4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-, (2S)-

There total 17 articles about 4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-, (2S)- 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: 85.0%

danishefsky's diene (54125-02-9) + (E)-benzalacetone (1896-62-4) → (+)-(S)-2-(trans-β-styryl)-2,3-dihydro-pyran-4-one (190835-53-1) + (R)-2-(E)-styryl-2,3-dihydro-4H-pyran-4-one (139627-54-6)

Guidance literature:

danishefsky's diene; (E)-benzalacetone; With C₃₆H₄₀ClCrN₂O₂S₂; In tert-butyl methyl ether; at 20 ℃; for 23h; Schlenk tube; Inert atmosphere;

With trifluoroacetic acid; In dichloromethane; for 0.5h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/ejoc.200701218

Reference yield: 75.0%

(E)-3-phenylpropenal (14371-10-9) + 1-dimethylamino-3-tert-butyl(dimethyl)silyloxy-1,3-butadiene → (+)-(S)-2-(trans-β-styryl)-2,3-dihydro-pyran-4-one (190835-53-1)

Guidance literature:

(E)-3-phenylpropenal; 1-dimethylamino-3-tert-butyl(dimethyl)silyloxy-1,3-butadiene; With Rh₂(S-BPTPI)4 trihydrate; In dichloromethane; at -40 ℃; for 6h; Inert atmosphere;

With acetyl chloride; In dichloromethane; at -78 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/b919535a

Reference yield: 41.0%

(2S,6S)-6-Isopropoxy-2-((E)-styryl)-3,6-dihydro-2H-pyran → (S)-goniothalamin (122046-62-2) + (+)-(S)-2-(trans-β-styryl)-2,3-dihydro-pyran-4-one (190835-53-1) + (Z)-6-styryl-5,6-dihydro-2-pyranone + (S)-2-((Z)-Styryl)-2,3-dihydro-pyran-4-one

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1055/s-2001-18088

upstream raw materials:

(E)-3-phenylpropenal

danishefsky's diene

benzyl bromide

(S)-6-chloromethyl-5,6-dihydropyran-2-one

Refernces

• 1、 Watanabe, Yudai,Washio, Takuya,Shimada, Naoyuki,Anada, Masahiro,Hashimoto, Shunichi. "Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates". supporting information; experimental part. p. 7294 - 7296. Retrieved 2010/06/13.
• 2、 Du, Haifeng,Zhang, Xue,Wang, Zheng,Bao, Hongli,You, Tianpa,Ding, Kuiling. "BINOlate-magnesium catalysts for enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes". scheme or table. p. 2248 - 2254. Retrieved 2009/04/08.