(R)-4-Methoxydalbergione

Base Information

• Chemical Name: (R)-4-Methoxydalbergione
• CAS No.: 4646-86-0
• Molecular Formula: C16H14O3
• Molecular Weight: 254.28
• DSSTox Substance ID: DTXSID10331958
• Nikkaji Number: J107.387G
• Wikidata: Q27135324
• Metabolomics Workbench ID: 23075
• ChEMBL ID: CHEMBL466581
• Mol file: 4646-86-0.mol

Synonyms:(R)-4-Methoxydalbergione;4646-86-0;(R)-4''-methoxydalbergione;CHEBI:66703;2-methoxy-5-[(1R)-1-phenylprop-2-enyl]cyclohexa-2,5-diene-1,4-dione;SCHEMBL716867;(R)-4' '-methoxydalbergione;CHEMBL466581;DTXSID10331958;LMPK12100072;AKOS040762945;Q27135324;2-methoxy-5-[(1R)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

Chemical Property of (R)-4-Methoxydalbergione

Chemical Property:

• Vapor Pressure: 1.81E-06mmHg at 25°C
• Boiling Point: 395.7°C at 760 mmHg
• Flash Point: 175.4°C
• PSA: 43.37000
• Density: 1.16g/cm³
• LogP: 2.56470
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 254.094294304
• Heavy Atom Count: 19
• Complexity: 451

Purity/Quality:

Analysis control,98.0% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=O)C(=CC1=O)C(C=C)C2=CC=CC=C2
• Isomeric SMILES: COC1=CC(=O)C(=CC1=O)[C@H](C=C)C2=CC=CC=C2
• Description: (R)-4-Methoxy dalbergione is the main allergen of Dalbergia nigra and Dalbergia latifolia Roxb. (East Indian rosewood, palissandre). Occupational sensitization occurs in timberworkers.

Technology Process of (R)-4-Methoxydalbergione

There total 6 articles about (R)-4-Methoxydalbergione 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: 61.0%

(R)-3-(2',4'-dimethoxyphenyl)-3-phenyl-1-propene (251317-25-6) → (R)-(+)-4-methoxydalbergione (4646-86-0)

Guidance literature:

(R)-3-(2',4'-dimethoxyphenyl)-3-phenyl-1-propene; With boron tribromide; In dichloromethane; at 0 ℃; for 1h;

With salcomine; oxygen; In N,N-dimethyl-formamide; for 4h; Further stages.;

DOI:10.1021/ol990961m

Reference yield:

7-methoxy-4-phenyl-2H-chromen-2-one (2555-31-9) → (R)-(+)-4-methoxydalbergione (4646-86-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 0 °C

2.1: 100 percent / potassium carbonate / acetone / Heating

3.1: hydrogen / [Rh((R,R)-bdpp)(NBD)]ClO₄ / methanol / 168 h / 60006 Torr

4.1: 81 percent / n-Bu₃P / tetrahydrofuran / 2 h

5.1: 100 percent / NaIO₄; NaHCO₃ / H₂O; methanol

6.1: BBr₃ / CH₂Cl₂ / 1 h / 0 °C

6.2: 61 percent / salcomine; oxygen / dimethylformamide / 4 h

With sodium periodate; lithium aluminium tetrahydride; tributylphosphine; hydrogen; boron tribromide; sodium hydrogencarbonate; potassium carbonate; [Rh((R,R)-bdpp)(NBD)]ClO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1021/ol990961m

Reference yield:

3-(2-hydroxy-4-methoxyphenyl)-3-phenyl allyl alcohol (10386-53-5) → (R)-(+)-4-methoxydalbergione (4646-86-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / potassium carbonate / acetone / Heating

2.1: hydrogen / [Rh((R,R)-bdpp)(NBD)]ClO₄ / methanol / 168 h / 60006 Torr

3.1: 81 percent / n-Bu₃P / tetrahydrofuran / 2 h

4.1: 100 percent / NaIO₄; NaHCO₃ / H₂O; methanol

5.1: BBr₃ / CH₂Cl₂ / 1 h / 0 °C

5.2: 61 percent / salcomine; oxygen / dimethylformamide / 4 h

With sodium periodate; tributylphosphine; hydrogen; boron tribromide; sodium hydrogencarbonate; potassium carbonate; [Rh((R,R)-bdpp)(NBD)]ClO₄; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

DOI:10.1021/ol990961m

upstream raw materials:

(R)-3-(2',4'-dimethoxyphenyl)-3-phenyl-1-propene

(R)-3-(2,4-dimethoxyphenyl)-3-phenylpropan-1-ol

(R)-1-phenylseleno-3-(2',4'-dimethoxyphenyl)-3-phenylpropane

7-methoxy-4-phenyl-2H-chromen-2-one

Downstream raw materials:

(R)-4-Methoxydalbergionhydrochinon-diacetat

4-Methoxy-dihydrodalbergion

Refernces