2-Methyl-1-phenyl-4-(phenylmethoxy)-1,3-butanedione

Base Information

• Chemical Name: 2-Methyl-1-phenyl-4-(phenylmethoxy)-1,3-butanedione
• CAS No.: 426833-01-4
• Molecular Formula: C₁₈H₁₈O₃
• Molecular Weight: 282.339
• DSSTox Substance ID: DTXSID801226011
• Nikkaji Number: J1.746.415I
• Mol file: 426833-01-4.mol

Synonyms:DTXSID801226011;426833-01-4;2-Methyl-1-phenyl-4-(phenylmethoxy)-1,3-butanedione

Chemical Property of 2-Methyl-1-phenyl-4-(phenylmethoxy)-1,3-butanedione

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 282.125594432
• Heavy Atom Count: 21
• Complexity: 338

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)COCC1=CC=CC=C1)C(=O)C2=CC=CC=C2

Technology Process of 2-Methyl-1-phenyl-4-(phenylmethoxy)-1,3-butanedione

There total 2 articles about 2-Methyl-1-phenyl-4-(phenylmethoxy)-1,3-butanedione 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: 72.0%

1-phenyl-propan-1-one (93-55-0) + 1-(1H-benzotriazol-1-yl)-2-benzyloxyethan-1-one (642993-51-9) → 4-benzyloxy-2-methyl-1-phenylbutane-1,3-dione (426833-01-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tetlet.2003.09.192

Reference yield:

benzyloxyacetic acid (30379-55-6) → 4-benzyloxy-2-methyl-1-phenylbutane-1,3-dione (426833-01-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / DCC / tetrahydrofuran / 12 h / 20 °C

2.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C

2.2: 72 percent / tetrahydrofuran / 1.75 h / -78 - 20 °C

With dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo035068m

Reference yield: 78.0%

4-benzyloxy-2-methyl-1-phenylbutane-1,3-dione (426833-01-4) → (-)-phenyl (2R,3R)-4-benzyloxy-3-hydroxy-2-methylbutanoate (642993-64-4)

Guidance literature:

4-benzyloxy-2-methyl-1-phenylbutane-1,3-dione; With formic acid; (R,R)-ruthenium; triethylamine; In dichloromethane; Heating;

With bis-trimethylsilanyl peroxide; C₆H₁₀(NHSO₂Tol)2; tin(IV) chloride; In dichloromethane; at 20 ℃;

With acetic acid; In tetrahydrofuran; water; for 24h;

DOI:10.1016/j.tetlet.2003.09.192

upstream raw materials:

1-phenyl-propan-1-one

1-(1H-benzotriazol-1-yl)-2-benzyloxyethan-1-one

benzyloxyacetic acid

Downstream raw materials:

(2S,3S)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid

(-)-(2R,3R)-4-benzyloxy-3-hydroxy-2-methyl-1-phenyl-butan-1-one

(-)-phenyl (2R,3R)-4-benzyloxy-3-hydroxy-2-methylbutanoate

(+)-(2S,3R)-4-benzyloxy-3-(tert-butyldimethylsiloxy)-2-methylbutan-1-ol