2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone

Base Information

• Chemical Name: 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone
• CAS No.: 35932-36-6
• Molecular Formula: C15H20O4
• Molecular Weight: 264.321
• UNII: LW94MTC8LE
• ChEMBL ID: CHEMBL3970720
• DSSTox Substance ID: DTXSID601148057
• Metabolomics Workbench ID: 49306
• Nikkaji Number: J1.061.562C
• Mol file: 35932-36-6.mol

Synonyms:2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone;35932-36-6;2-(2-methylpropanoyl)-4-prenylphloroglucinol;2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-1-propanone;2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one;2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]propan-1-one;dimethylallyl-phlorisobutyrophenone;LW94MTC8LE;4-prenylphlorisobutanophenone;CHEMBL3970720;SCHEMBL24075565;CHEBI:134342;IOBXAMCSYCVNET-UHFFFAOYSA-N;DTXSID601148057;2-isobutyryl-4-prenylphloroglucinol;2-isobutanoyl-4-prenylphloroglucinol;2-(2-methylpropionyl)-4-prenylphloroglucinol;2-(3',3'-dimethylallyl)-4-isobutyrylphloroglucinol;{3-(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-propyl) ketone;1-Propanone, 2-methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-;2-Methyl-1-(3-(3-methylbut-2-enyl)-2,4,6-tris(oxidanyl)phenyl)propan-1-one

Chemical Property of 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 344

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=O)C1=C(C=C(C(=C1O)CC=C(C)C)O)O

Technology Process of 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone

There total 5 articles about 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 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: 43.0%

phlorisobutyrophenone (35458-21-0) + prenyl bromide (870-63-3) → 2-methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)propan-1-one (35932-36-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.5b00721 DOI:10.1021/acs.jnatprod.6b00224

Reference yield: 36.0%

phlorisobutyrophenone (35458-21-0) + 3-methyl-2-buten-1-ol (556-82-1) → 2-methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)propan-1-one (35932-36-6)

Guidance literature:

With aluminum oxide; In ethyl acetate; for 24h; Reflux;

Reference yield:

3,5-dihydroxyphenol (108-73-6) → 2-methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)propan-1-one (35932-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum (III) chloride / nitrobenzene / 65 °C

2: calcium chloride; glycerol; dimethyl sulfoxide; fungal indole prenyltransferase AnaPT / aq. buffer / 6 h / 37 °C / pH 7.5 / Enzymatic reaction

With aluminum (III) chloride; fungal indole prenyltransferase AnaPT; dimethyl sulfoxide; glycerol; calcium chloride; In nitrobenzene; 1: |Friedel-Crafts Acylation / 2: |Friedel-Crafts Alkylation;

DOI:10.1021/np5009784

upstream raw materials:

phlorisobutyrophenone

prenyl bromide

3-methyl-2-buten-1-ol

dimethylallyl diphosphate

Downstream raw materials:

3-<3',3'-dimethylallyl-(1')>-1-isobutyryl-phloroglucinol-6-O-methyl ether

3'-(3-methyl-2-butenyl)-2',4',6'-triacetoxyisobutyrophenone