(E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid

Base Information

• Chemical Name: (E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid
• CAS No.: 73408-03-4
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.242
• Mol file: 73408-03-4.mol

Synonyms:

Chemical Property of (E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid

There total 6 articles about (E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid 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:

(2E,4E)-2-methyl-5-phenyl-2,4-pentadienoic acid (20414-94-2) → (E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid (73408-03-4,73408-04-5,137245-81-9) + (E)-(2R)-5-Phenyl-2-methyl-4-pentenoic acid (171483-81-1)

Guidance literature:

With bis(norbornadiene)rhodium(l)tetrafluoroborate; chenphos; hydrogen; triethylamine; In methanol; at 20 ℃; for 24h; under 22801.5 Torr; enantioselective reaction; Glovebox;

DOI:10.1021/acs.orglett.0c00915

Reference yield:

benzaldehyde (100-52-7) → (E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid (73408-03-4,73408-04-5,137245-81-9) + (E)-(2R)-5-Phenyl-2-methyl-4-pentenoic acid (171483-81-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / Inert atmosphere; Cooling

3.1: Dess-Martin periodane / dichloromethane / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: sodium hydroxide / methanol / 20 °C / Inert atmosphere

6.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; triethylamine; chenphos; hydrogen / methanol / 24 h / 20 °C / 22801.5 Torr / Glovebox

With bis(norbornadiene)rhodium(l)tetrafluoroborate; n-butyllithium; chenphos; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1021/acs.orglett.0c00915

Reference yield:

methyl cinnamate (103-26-4,1754-62-7) → (E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid (73408-03-4,73408-04-5,137245-81-9) + (E)-(2R)-5-Phenyl-2-methyl-4-pentenoic acid (171483-81-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / Inert atmosphere; Cooling

2.1: Dess-Martin periodane / dichloromethane / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: sodium hydroxide / methanol / 20 °C / Inert atmosphere

5.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; triethylamine; chenphos; hydrogen / methanol / 24 h / 20 °C / 22801.5 Torr / Glovebox

With bis(norbornadiene)rhodium(l)tetrafluoroborate; n-butyllithium; chenphos; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1021/acs.orglett.0c00915

upstream raw materials:

3-Phenylpropenol

benzaldehyde

methyl cinnamate

3-phenyl-propenal

Downstream raw materials:

(2S,4E)-2-methyl-5-phenyl-4-penten-1-ol

((R)-4,8-dimethyl-non-1-en-t-yl)-benzene

((4R,8R)-4,8,12-trimethyl-tridec-1-en-t-yl)-benzene

Toluene-4-sulfonic acid (E)-(S)-2-methyl-5-phenyl-pent-4-enyl ester