(2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide

Base Information

• Chemical Name: (2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide
• CAS No.: 153077-13-5
• Molecular Formula: C₂₃H₃₃NO₃
• Molecular Weight: 371.52
• Mol file: 153077-13-5.mol

Synonyms:(2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide

Chemical Property of (2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide

There total 9 articles about (2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide 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: 97.0%

Ethyl (2S,2'E,4'E,6'R)-2-(4,6-dimethyldodeca-2,4-dienoylamido)-3-(4-hydroxyphenyl)propanoate (153152-86-4) → (2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide (153077-13-5)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; n-heptane; at -78 ℃; for 3h;

DOI:10.1039/p19960001385

Reference yield:

(R)-α-methyloctanal (7786-29-0,55352-42-6,72598-55-1,49642-49-1) → (2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide (153077-13-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / toluene / 3 h / Heating

2: 98 percent / DIBAL-H / hexane; tetrahydrofuran / 3 h / -78 °C

3: 100 percent / MnO₂ / CH₂Cl₂ / 2 h / Heating

4: 87 percent / toluene / 3.5 h / Heating

5: 81 percent / aq. LiOH / tetrahydrofuran; methanol / 12 h / Ambient temperature

6: 73 percent / Ph₂POCl, Et₃N / tetrahydrofuran / 1.) r.t., 30 min, 2.) r.t., 6 h

7: 97 percent / DIBAL-H / heptane; tetrahydrofuran / 3 h / -78 °C

With manganese(IV) oxide; lithium hydroxide; diisobutylaluminium hydride; triethylamine; Diphenylphosphinic chloride; In tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; toluene;

DOI:10.1039/p19960001385

Reference yield:

(R)-2-methyloctan-1-ol (120925-50-0) → (2E,4E)-(R)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide (153077-13-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) -78 to 0 deg C, 45 min

2: 84 percent / toluene / 3 h / Heating

3: 98 percent / DIBAL-H / hexane; tetrahydrofuran / 3 h / -78 °C

4: 100 percent / MnO₂ / CH₂Cl₂ / 2 h / Heating

5: 87 percent / toluene / 3.5 h / Heating

6: 81 percent / aq. LiOH / tetrahydrofuran; methanol / 12 h / Ambient temperature

7: 73 percent / Ph₂POCl, Et₃N / tetrahydrofuran / 1.) r.t., 30 min, 2.) r.t., 6 h

8: 97 percent / DIBAL-H / heptane; tetrahydrofuran / 3 h / -78 °C

With manganese(IV) oxide; lithium hydroxide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; Diphenylphosphinic chloride; In tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; toluene;

DOI:10.1039/p19960001385

upstream raw materials:

Ethyl (2S,2'E,4'E,6'R)-2-(4,6-dimethyldodeca-2,4-dienoylamido)-3-(4-hydroxyphenyl)propanoate

(R)-α-methyloctanal

(R)-2-methyloctan-1-ol

(2E,4R)-2,4-Dimethyl-2-decenal

Downstream raw materials:

Aranorosin

aranorosin