2,3-Dehydrokievitone

Base Information

• Chemical Name: 2,3-Dehydrokievitone
• CAS No.: 74161-25-4
• Molecular Formula: C20H18O6
• Molecular Weight: 354.359
• UNII: M463PIR1IG
• DSSTox Substance ID: DTXSID10225121
• Nikkaji Number: J227.953C
• Wikidata: Q27283469
• Metabolomics Workbench ID: 22425
• ChEMBL ID: CHEMBL4086888
• Mol file: 74161-25-4.mol

Synonyms:2,3-Dehydrokievitone;74161-25-4;3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(3-methylbut-2-enyl)chromen-4-one;BRN 4333751;UNII-M463PIR1IG;M463PIR1IG;5,7-Dihydroxy-3-(2,4-dihydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;5,7,2',4'-Tetrahydroxy-8-prenylisoflavone;2',4',5,7-tetrahydroxy-8-prenylisoflavone;4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(2,4-dihydroxyphenyl)-8-(3-methyl-2-butenyl)-;2,3-DHKV;CHEMBL4086888;DTXSID10225121;CHEBI:175549;GLXC-18492;HY-N1653;LMPK12050288;AKOS032948668;LS-39591;XD161868;CS-0017315;FT-0775821;Q27283469;4H-1-BENZOPYRAN-4-ONE, 3-(2,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-8-(3-METHYL-2-BUTEN-1-YL)-;4H-1-BENZOPYRAN-4-ONE, 3-(2,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-8-(3-METHYL-2-BUTENYL)-

Chemical Property of 2,3-Dehydrokievitone

Chemical Property:

• Vapor Pressure: 1.29E-16mmHg at 25°C
• Boiling Point: 633°Cat760mmHg
• PKA: 6.46±0.20(Predicted)
• Flash Point: 229.8°C
• PSA: 111.13000
• Density: 1.424g/cm³
• LogP: 3.79110
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 354.11033829
• Heavy Atom Count: 26
• Complexity: 593

Purity/Quality:

≥97% ^*data from raw suppliers

2,3-Dehydrokievitone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C(=CO2)C3=C(C=C(C=C3)O)O)C

Technology Process of 2,3-Dehydrokievitone

There total 8 articles about 2,3-Dehydrokievitone 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: 88.0%

2',4',5,7-tetrakis(benzoyloxy)-8-(3-methyl-2-butenyl)isoflavone (160154-76-7) → 5,7,2',4'-tetrahydroxy-8-(3,3-dimethylallyl)isoflavone (74161-25-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; methanol; at 45 ℃; for 0.666667h;

DOI:10.1246/bcsj.71.2673

Reference yield:

2-methyl-but-3-yn-2-ol (115-19-5) → 5,7,2',4'-tetrahydroxy-8-(3,3-dimethylallyl)isoflavone (74161-25-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / Et₃N, PdCl₂, PPh₃, CuI / dimethylformamide / 2 h / 80 °C

2: 74 percent / H₂ / Pd/C / methanol; ethyl acetate / 15 - 18 °C

3: 70 percent / K₂CO₃ / acetone / 7 h / Heating

4: 112 mg / TsOH*H₂O / toluene / 1 h / 115 °C

5: 88 percent / aq. NaOH / methanol; dioxane / 0.67 h / 45 °C

With sodium hydroxide; copper(l) iodide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; palladium dichloride; palladium on activated charcoal; In 1,4-dioxane; methanol; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1246/bcsj.71.2673

Reference yield:

2',4',5,7-tetrakis(benzyloxy)-8-iodoisoflavone (160154-73-4) → 5,7,2',4'-tetrahydroxy-8-(3,3-dimethylallyl)isoflavone (74161-25-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / Et₃N, PdCl₂, PPh₃, CuI / dimethylformamide / 2 h / 80 °C

2: 74 percent / H₂ / Pd/C / methanol; ethyl acetate / 15 - 18 °C

3: 70 percent / K₂CO₃ / acetone / 7 h / Heating

4: 112 mg / TsOH*H₂O / toluene / 1 h / 115 °C

5: 88 percent / aq. NaOH / methanol; dioxane / 0.67 h / 45 °C

With sodium hydroxide; copper(l) iodide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; palladium dichloride; palladium on activated charcoal; In 1,4-dioxane; methanol; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1246/bcsj.71.2673

upstream raw materials:

2',4',5,7-tetrakis(benzoyloxy)-8-(3-methyl-2-butenyl)isoflavone

2-methyl-but-3-yn-2-ol

2',4',5,7-tetrahydroxy-8-(3-hydroxy-3-methylbutyl)isoflavone

2',4',5,7-tetrakis(benzyloxy)-8-iodoisoflavone

Downstream raw materials:

7-O-methyl-2,3-dehydrokievitone-(-)-epoxide

7-O-methyl-2,3-dehydrokievitone

3-(2,4-Dihydroxy-phenyl)-5-hydroxy-8-(1-hydroxy-1-methyl-ethyl)-8,9-dihydro-furo[2,3-h]chromen-4-one

Refernces

• 1、 Tsukayama, Masao,Tsurumoto, Ken,Kishimoto, Kazuto,Higuchi, Daisuke. "Regioselective Synthesis of Prenylisoflavones. Syntheses of 2,3-Dehydrokievitone and Related Compounds". . p. 2101 - 2104. Retrieved 2007/10/02.