Xenognosin A

Base Information

• Chemical Name: Xenognosin A
• CAS No.: 76907-79-4
• Molecular Formula: C16H16O3
• Molecular Weight: 256.2964
• UNII: 02F52L203E
• ChEMBL ID: CHEMBL1087026
• DSSTox Substance ID: DTXSID801318553
• Metabolomics Workbench ID: 43890
• Nikkaji Number: J2.766.817H
• Wikidata: Q27108572
• Mol file: 76907-79-4.mol

Synonyms:xenognosin;Xenognosin A;76907-79-4;UNII-02F52L203E;Phenol, 4-((2E)-3-(4-hydroxyphenyl)-2-propen-1-yl)-3-methoxy-;02F52L203E;CHEBI:10075;Phenol, 4-((2E)-3-(4-hydroxyphenyl)-2-propenyl)-3-methoxy-;C08731;1-(4-hydroxyphenyl)-3-(4-hydroxy-2-methoxyphenyl)propene;CHEMBL1087026;4-[(E)-3-(4-hydroxyphenyl)prop-2-enyl]-3-methoxyphenol;DTXSID801318553;AKOS030547993;4-[3-(4-hydroxyphenyl)prop-2-enyl]-3-methoxy-phenol;Q27108572;4-[3-(4-Hydroxyphenyl)-2-propenyl]-3-methoxyphenol, 9CI;4-[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenol

Chemical Property of Xenognosin A

Chemical Property:

• Vapor Pressure: 1.49E-08mmHg at 25°C
• Boiling Point: 445.6°Cat760mmHg
• Flash Point: 223.3°C
• PSA: 49.69000
• Density: 1.209g/cm³
• LogP: 3.36230
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 256.109944368
• Heavy Atom Count: 19
• Complexity: 282

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)O)CC=CC2=CC=C(C=C2)O
• Isomeric SMILES: COC1=C(C=CC(=C1)O)C/C=C/C2=CC=C(C=C2)O

Technology Process of Xenognosin A

There total 15 articles about Xenognosin A 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: 90.0%

4-(tert-Butyl-dimethyl-silanyloxy)-1-{(E)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-allyl}-2-methoxy-benzene (82861-25-4) → xenognosin A (76907-79-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)87153-1

Reference yield:

7-hydroxy-2H-chromen-2-one (93-35-6) → xenognosin A (76907-79-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / 10percent aq. NaOH, methyltrialkyl(C₈-C₁₀)ammonium chloride (Adogen 464) / CH₂Cl₂ / 2 h

2: 97 percent / H₂ / 10percent Pd/C / 24 h / 775.7 Torr

3: 96 percent / K₂CO₃ / acetone / 5 h / Heating

4: 94 percent / LiAlH₄ / diethyl ether / 4 h / Heating

5: 92 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h

6: 1.) sec-butyllithium / 1.) THF, n-hexane, -78 deg C, 30 min, 2.) a) -78 deg C, 10 min, b) RT, 10 min

7: 55 percent / Me₂SO / 1.5 h / 160 - 165 °C

With sodium hydroxide; lithium aluminium tetrahydride; methyltrialkyl(C₈-C₁₀)ammonium chloride (Adogen 464); hydrogen; sec.-butyllithium; potassium carbonate; dimethyl sulfoxide; pyridinium chlorochromate; palladium on activated charcoal; In diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo00347a032

Reference yield:

7-(methoxymethoxy)-2H-chromen-2-one (80754-21-8) → xenognosin A (76907-79-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / H₂ / 10percent Pd/C / 24 h / 775.7 Torr

2: 96 percent / K₂CO₃ / acetone / 5 h / Heating

3: 94 percent / LiAlH₄ / diethyl ether / 4 h / Heating

4: 92 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h

5: 1.) sec-butyllithium / 1.) THF, n-hexane, -78 deg C, 30 min, 2.) a) -78 deg C, 10 min, b) RT, 10 min

6: 55 percent / Me₂SO / 1.5 h / 160 - 165 °C

With lithium aluminium tetrahydride; hydrogen; sec.-butyllithium; potassium carbonate; dimethyl sulfoxide; pyridinium chlorochromate; palladium on activated charcoal; In diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo00347a032

upstream raw materials:

O-methylresorcine

(E)-4-(3-hydroxyprop-1-enyl)phenol

4-(tert-Butyl-dimethyl-silanyloxy)-1-{(E)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-allyl}-2-methoxy-benzene

7-hydroxy-2H-chromen-2-one

Downstream raw materials:

2,4-Dimethoxy-1-[(E)-3-(4-methoxy-phenyl)-allyl]-benzene