4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone

Base Information

• Chemical Name: 4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone
• CAS No.: 90486-63-8
• Molecular Formula: C₂₂H₂₀O₇
• Molecular Weight: 396.397
• Mol file: 90486-63-8.mol

Synonyms:4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone

Chemical Property of 4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone

There total 28 articles about 4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone 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: 74.0%

3-(4-benzoyloxy-2,5-dimethoxyphenyl)-8,8-dimethyl-5-tosyloxy-4H,8H-benzo<1,2-b:3,4-b'>dipyran-4-one (124360-83-4) → 4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone (90486-63-8)

Guidance literature:

With potassium hydroxide;

DOI:10.1246/bcsj.62.826

Reference yield: 51.0%

4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethyldihydropyrano<6,5-h>isoflavone (90486-62-7) → 4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone (90486-63-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chlorobenzene; at 140 ℃; for 2h;

DOI:10.1248/cpb.36.592

Reference yield:

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) → 4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone (90486-63-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 4 percent / PPA / dioxane / 3 h / 60 °C

2: 64 percent / K₂CO₃ / acetone / 1.5 h / Heating

3: 88 percent / K₂CO₃ / acetone / 3.5 h / Heating

4: 95 percent / K₂CO₃ / methanol / 1.5 h / Heating

5: 60 percent / piperidine, pyridine / ethanol / 14 h / Heating

6: NaOAc

7: 1.) thallium(III) nitrate; 2.) 10percent HCl / 1.) MeOH, 36-38 deg C, 10 h; 2.) MeOH, reflux, 3 h

8: 91 percent / AlBr₃ / acetonitrile / 0.42 h / 40 °C

9: 92 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate

10: 80 percent / K₂CO₃ / acetone / 6 h / Heating

11: 46 percent / NaBH₄ / PdCl₂ / tetrahydrofuran; H₂O / 0.67 h / 14 - 17 °C

12: 92 percent / TsOH*H₂O / toluene / 0.33 h / Heating

13: 20percent KOH / ethanol / 0.67 h / Heating

With piperidine; pyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; aluminum tri-bromide; hydrogen; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; thallium(III) nitrate; palladium on activated charcoal; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; ethyl acetate; acetone; toluene; acetonitrile;

DOI:10.1246/bcsj.62.826

upstream raw materials:

4',5-dihydroxy-2',5'-dimethoxy-2,2-dimethyldihydropyrano<6,5-h>isoflavone

3-(4-benzoyloxy-2,5-dimethoxyphenyl)-8,8-dimethyl-5-tosyloxy-4H,8H-benzo<1,2-b:3,4-b'>dipyran-4-one

7-<2,5-dimethoxy-4-(tosyloxy)phenyl>-2,2-dimethyl-5-tosyloxy-2H,6H-benzo<1,2-b:5,4-b'>dipyran-6-one

3-Methylbutenoic acid

Downstream raw materials:

2',4',5,5'-tetramethoxy-2,2-dimethylpyrano<6,5-h>isoflavone

5-hydroxy-2',4',5'-trimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone

4',5-diacetoxy-2',5'-dimethoxy-2,2-dimethylpyrano<6,5-h>isoflavone

Refernces

• 1、 Tsukayama,Horie,Iguchi,Nakayama. "Synthesis of pyranoisoflavones by the oxidative rearrangement of dihydropyranochalcones with thallium(III) nitrate: Synthesis of elongatin, its angular isomer, toxicarol isoflavone, and related compounds". . p. 592 - 600. Retrieved 2007/10/02.