1-Penten-4-yn-3-one, 1-[2-[(3Z)-7-iodo-4-methyl-3-hepten-1-yl]-4-methoxyphenyl]-, (1E)-

Base Information

• Chemical Name: 1-Penten-4-yn-3-one, 1-[2-[(3Z)-7-iodo-4-methyl-3-hepten-1-yl]-4-methoxyphenyl]-, (1E)-
• CAS No.: 921229-07-4
• Molecular Formula: C20H23IO2
• Molecular Weight: 422.306
• Mol file: 921229-07-4.mol

Synonyms:

Chemical Property of 1-Penten-4-yn-3-one, 1-[2-[(3Z)-7-iodo-4-methyl-3-hepten-1-yl]-4-methoxyphenyl]-, (1E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Penten-4-yn-3-one, 1-[2-[(3Z)-7-iodo-4-methyl-3-hepten-1-yl]-4-methoxyphenyl]-, (1E)-

There total 11 articles about 1-Penten-4-yn-3-one, 1-[2-[(3Z)-7-iodo-4-methyl-3-hepten-1-yl]-4-methoxyphenyl]-, (1E)- 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: 92.0%

(1E)-1-(2-(7-chloro-4-methylhept-3-enyl)-4-methoxyphenyl)pent-1-en-4-yn-3-one (921229-30-3) → (1E)-1-(2-(7-iodo-4-methylhept-3-enyl)-4-methoxyphenyl)pent-1-en-4-yn-3-one (921229-07-4)

Guidance literature:

With potassium carbonate; sodium iodide; In butanone; for 23h; Heating;

DOI:10.1039/b703373g

Reference yield:

(rac)-5-{[tert-butyl(diphenyl)silyl]oxy}pentan-2-ol (558465-78-4) → (1E)-1-(2-(7-iodo-4-methylhept-3-enyl)-4-methoxyphenyl)pent-1-en-4-yn-3-one (921229-07-4)

Guidance literature:

Multi-step reaction with 10 steps

1: MCPBA

2: 38 percent / NaHMDS / tetrahydrofuran / -78 °C

3: TBAF / tetrahydrofuran / 0 - 25 °C

4: 97 percent / NCS; K₂CO₃; PPh₃ / CH₂Cl₂ / 0 °C

5: 86 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 89 percent / MnO₂ / CH₂Cl₂

7: 98 percent / tetrahydrofuran / -78 - 25 °C

8: 86 percent / MnO₂ / CH₂Cl₂

9: 92 percent / NaI; K₂CO₃ / butan-2-one

With manganese(IV) oxide; N-chloro-succinimide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; In tetrahydrofuran; dichloromethane; butanone; 3: Julia olefination;

DOI:10.1055/s-2006-951533

Reference yield:

2-[4-(tert-butyldiphenyl-silanyloxy)-1-methyl-butylsulfanyl]-benzothiazole (944382-83-6) → (1E)-1-(2-(7-iodo-4-methylhept-3-enyl)-4-methoxyphenyl)pent-1-en-4-yn-3-one (921229-07-4)

Guidance literature:

Multi-step reaction with 9 steps

1: MCPBA

2: 38 percent / NaHMDS / tetrahydrofuran / -78 °C

3: TBAF / tetrahydrofuran / 0 - 25 °C

4: 97 percent / NCS; K₂CO₃; PPh₃ / CH₂Cl₂ / 0 °C

5: 86 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 89 percent / MnO₂ / CH₂Cl₂

7: 98 percent / tetrahydrofuran / -78 - 25 °C

8: 86 percent / MnO₂ / CH₂Cl₂

9: 92 percent / NaI; K₂CO₃ / butan-2-one

With manganese(IV) oxide; N-chloro-succinimide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; In tetrahydrofuran; dichloromethane; butanone; 2: Julia olefination;

DOI:10.1055/s-2006-951533

upstream raw materials:

(1E)-1-(2-(7-chloro-4-methylhept-3-enyl)-4-methoxyphenyl)pent-1-en-4-yn-3-one

(rac)-5-{[tert-butyl(diphenyl)silyl]oxy}pentan-2-ol

2-[4-(tert-butyldiphenyl-silanyloxy)-1-methyl-butylsulfanyl]-benzothiazole

2-[5-(tert-butyl-diphenyl-silanoxy)-pentane-2-sulfonyl]-benzothiazole