Derrone

Base Information

• Chemical Name: Derrone
• CAS No.: 76166-59-1
• Molecular Formula: C20H16 O5
• Molecular Weight: 336.344
• Mol file: 76166-59-1.mol

Synonyms:Derrone

Chemical Property of Derrone

Chemical Property:

• Boiling Point: 584.1±50.0 °C(Predicted)
• PKA: 6.47±0.40(Predicted)
• PSA: 79.90000
• Density: 1.368±0.06 g/cm3(Predicted)
• LogP: 4.05540

Purity/Quality:

98% ^*data from raw suppliers

Derrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Derrone

There total 31 articles about Derrone 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%

lupiwighteone (104691-86-3) → atalantoflavone (76166-59-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 80 ℃; for 1h;

Reference yield:

3-(4-Benzyloxy-phenyl)-5-hydroxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-4-one (141737-97-5) → atalantoflavone (76166-59-1)

Guidance literature:

With boron trichloride; In dichloromethane; at -70 ℃; for 0.25h;

DOI:10.3987/COM-91-5918

Reference yield:

3-Iod-2-hydroxy-4,6-dibenzyloxy-acetophenon (95165-66-5) → atalantoflavone (76166-59-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1.25 h / Ambient temperature

2: KOH / ethanol / 4.5 h / Heating

3: conc. aq. HCl / CHCl₃; ethanol / 1 h / 40 °C

4: 94 percent / pyridine / 2 h / 110 °C

5: 69 percent / thallium (III) nitrate trihydrate / CHCl₃ / 7 h / 40 °C

6: 79 percent / 10percent aq. NaOH / tetrahydrofuran / 3 h / Ambient temperature

7: 82 percent / Et₃N, PdCl₂, PPh₃, CuI / dimethylformamide / 2.5 h / 80 °C

8: 82 percent / H₂ / Raney Ni / tetrahydrofuran; methanol / 18 °C

9: 80 percent / K₂CO₃ / acetone / 2.5 h / Heating

10: 1.) BF₃*Et₂O, 2.) pyridine / 1.) CH₂Cl₂, RT, 4 h, 2.) 105 deg C, 1.5 h

11: 93 percent / 10percent aq. NaOH / tetrahydrofuran; methanol / 0.83 h / 50 °C

12: 72 percent / DDQ / toluene / 1 h / 80 °C

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; copper(l) iodide; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; thallium(III) nitrate; palladium dichloride; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene;

upstream raw materials:

5-hydroxy-3(4'-hydroxy)phenyl-8,8-dimethyl-9,10-dihydro-4H,8H-benzo<1,2b:5,6b'>dipyran-4-one

3-(4-Benzyloxy-phenyl)-5-hydroxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-4-one

lupiwighteone

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

Downstream raw materials:

5-hydroxy-3(4'-methoxy)phenyl-8,8-dimethyl-4H,8H-benzo<1,2b:5,6b'>dipyran-4-one

Refernces

• 1、 Tsukayama, Masao,Kawamura, Yasuhiko,Tahara, Hideo. "SYNTHESIS OF 4',5- AND 3',4',5-OXYGENATED PYRANOISOFLAVONES: ALPINUM ISOFLAVONE AND RELATED COMPOUNDS, AND REVISED STRUCTURE OF DERRONE". . p. 505 - 516. Retrieved 2007/10/02.