(E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid

Base Information

• Chemical Name: (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid
• CAS No.: 144562-61-8
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444
• Mol file: 144562-61-8.mol

Synonyms:(E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid

Chemical Property of (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid

There total 10 articles about (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic 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: 74.0%

(E)-3-(2,4,5-Trimethoxy-3,6-dimethylphenyl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid (144562-60-7) → (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid (144562-61-8)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; for 0.5h;

DOI:10.1021/jm950725r

Reference yield:

cerium (IV) ammonium nitrate + (E)-3-(2,4,5-Trimethoxy-3,6-dimethylphenyl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid (144562-60-7) → (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid (144562-61-8)

Guidance literature:

With sodium chloride; sodium hydrogencarbonate; In water; acetonitrile;

Reference yield:

2,5-dimethoxy-3,6-dimethylbenzaldehyde (104129-40-0) → (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid (144562-61-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) m-CPBA, 2.) sodium methoxide / 1.) CH₂Cl₂, reflux, 30 min, 2.) methanol, RT, 30 min

2: 1.) TiCl₄ / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) CH₂Cl₂, RT, 2.5 h

3: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, RT, 3 h

4: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 50 deg C, overnight

5: 100 percent / NaOH / ethanol; H₂O / 1 h / Heating

6: 74 percent / cerium(IV) ammonium nitrate / H₂O; acetonitrile / 0.5 h

With sodium hydroxide; ammonium cerium(IV) nitrate; sodium methylate; titanium tetrachloride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In ethanol; water; acetonitrile;

DOI:10.1021/jm950725r

upstream raw materials:

(E)-3-(2,4,5-Trimethoxy-3,6-dimethylphenyl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid

2,5-dimethoxy-3,6-dimethylbenzaldehyde

5-pyridin-3-yl-pentan-1-ol

3-(5-Chloro-pentyl)-pyridine