7-Methoxy-5-prenyloxycoumarin

Base Information

• Chemical Name: 7-Methoxy-5-prenyloxycoumarin
• CAS No.: 35590-41-1
• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.29
• UNII: ZD7D2TE69K
• ChEMBL ID: CHEMBL513279
• DSSTox Substance ID: DTXSID20568319
• Metabolomics Workbench ID: 45809
• Nikkaji Number: J475.315A
• Wikidata: Q72518091
• Mol file: 35590-41-1.mol

Synonyms:7-methoxy-5-prenyloxycoumarin;35590-41-1;CHEMBL513279;7-methoxy-5-(3-methylbut-2-enoxy)chromen-2-one;7-Methoxy-5-((3-methylbut-2-en-1-yl)oxy)-2H-chromen-2-one;7-methoxy-5-[(3-methylbut-2-en-1-yl)oxy]-2H-chromen-2-one;ZD7D2TE69K;DTXSID20568319;CHEBI:174415;HSJZJYCOXHKDBJ-UHFFFAOYSA-N;BDBM50292576;7-Methoxy-5-[(3-methyl-2-buten-1-yl)oxy]-2H-1-benzopyran-2-one;7-Methoxy-5-[(3-methylbut-2-en-1-yl)oxy]-2H-1-benzopyran-2-one;2H-1-Benzopyran-2-one, 7-methoxy-5-[(3-methyl-2-buten-1-yl)oxy]-

Chemical Property of 7-Methoxy-5-prenyloxycoumarin

Chemical Property:

• PSA: 48.67000
• Density: 1.159
• LogP: 3.14660
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 260.10485899
• Heavy Atom Count: 19
• Complexity: 382

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCOC1=CC(=CC2=C1C=CC(=O)O2)OC)C

Technology Process of 7-Methoxy-5-prenyloxycoumarin

There total 7 articles about 7-Methoxy-5-prenyloxycoumarin 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:

5,7-dihydroxycoumarin 7-methyl ether (23053-61-4) + prenyl bromide (870-63-3) → 5-(isopent-2'-enyloxy)-7-methoxycoumarin (35590-41-1)

Guidance literature:

5,7-dihydroxycoumarin 7-methyl ether; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.5h;

prenyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 12h;

DOI:10.1007/s11418-017-1108-3

Reference yield:

5,7-dihydroxy-2H-chromen-2-one (2732-18-5) → 5-(isopent-2'-enyloxy)-7-methoxycoumarin (35590-41-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 6.3 g / pyridine / 2 h / Heating

2: 9.0 g / K₂CO₃ / acetone / 14 h / Ambient temperature

3: 4.9 mg / 1percent aq. NaHCO₃ / methanol / 0.5 h / Heating

4: 29.9 mg / K₂CO₃ / acetone / 3 h / Heating

With pyridine; sodium hydrogencarbonate; potassium carbonate; In methanol; acetone;

DOI:10.1248/cpb.39.2509

Reference yield:

7-acetoxy-5-(3'-methyl-2'-butenyloxy)coumarin (59036-51-0) → 5-(isopent-2'-enyloxy)-7-methoxycoumarin (35590-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.9 mg / 1percent aq. NaHCO₃ / methanol / 0.5 h / Heating

2: 29.9 mg / K₂CO₃ / acetone / 3 h / Heating

With sodium hydrogencarbonate; potassium carbonate; In methanol; acetone;

DOI:10.1248/cpb.39.2509

upstream raw materials:

5-(2-enyl-3-methylbut)oxy-7-hydroxycoumarin

methyl iodide

7-acetoxy-5-(3'-methyl-2'-butenyloxy)coumarin

5,7-dihydroxy-2H-chromen-2-one

Refernces

• 1、 Ito,Fujiwara,Kajita,Ju-ichi,Takemura,Suzuki,Tanaka,Omura,Furukawa. "New coumarins from Citrus plants". . p. 2509 - 2513. Retrieved 2007/10/02.