(1S,3R)-1,7,9-Trihydroxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione

Base Information

• Chemical Name: (1S,3R)-1,7,9-Trihydroxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione
• CAS No.: 138310-59-5
• DSSTox Substance ID: DTXSID301038865
• Nikkaji Number: J1.639.137I
• ChEMBL ID: CHEMBL320539
• Mol file: 138310-59-5.mol

Synonyms:CHEMBL320539;(+)-Thysanone;DTXSID301038865;BDBM50107010;(1S,3R)-1,7,9-Trihydroxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione;138310-59-5

Chemical Property of (1S,3R)-1,7,9-Trihydroxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 276.06338810
• Heavy Atom Count: 20
• Complexity: 496

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2=C(C(O1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O
• Isomeric SMILES: C[C@@H]1CC2=C([C@H](O1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O

Technology Process of (1S,3R)-1,7,9-Trihydroxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione

There total 11 articles about (1S,3R)-1,7,9-Trihydroxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione 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: 89.0%

(S)-(+)-3,4-dihydro-7,9-dihydroxy-3-methyl-1H-naphtho[2,3-c]pyran-5,10-dione (233253-24-2) → (1R,3S)-(-)-thysanone (138310-59-5,233279-24-8)

Guidance literature:

(S)-(+)-3,4-dihydro-7,9-dihydroxy-3-methyl-1H-naphtho[2,3-c]pyran-5,10-dione; With bromine; dibenzoyl peroxide; In tetrachloromethane; for 1h; Reflux; Irradiation;

With water; In tetrahydrofuran; tetrachloromethane; for 0.5h;

DOI:10.1055/s-2008-1078590

Reference yield:

1-bromo-7,9-dihydroxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione → (1R,3S)-(-)-thysanone (138310-59-5,233279-24-8)

Guidance literature:

With water; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1039/b111446h

Reference yield:

(S)-mellein (480-33-1,1200-93-7,17397-85-2,62623-84-1) → (1R,3S)-(-)-thysanone (138310-59-5,233279-24-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 91 percent / NBS / dimethylformamide / 16 h / 20 °C

2.1: 98 percent / K₂CO₃ / acetone / 0.75 h / Heating

3.1: 95 percent / DIBAL-H / toluene / 1.5 h / -70 - 20 °C

4.1: CF₃COOH / CH₂Cl₂ / 0.25 h / 0 - 20 °C

4.2: 98 percent / Et₃SiH / CH₂Cl₂ / 1.75 h / 0 - 20 °C

5.1: 86 percent / (PhCH₂Se)2; NaBH₄ / dimethylformamide / 1.5 h / Heating

6.1: 93 percent / aq. cerium(IV) ammonium nitrate / acetonitrile / 0.5 h / 20 °C

7.1: 73 percent / toluene / 3 h / Heating

8.1: Br₂ / CCl₄ / 0.5 h / Irradiation

9.1: 8.3 mg / H₂O / tetrahydrofuran / 1 h / 20 °C

With sodium tetrahydroborate; N-Bromosuccinimide; ammonium cerium(IV) nitrate; dibenzyl diselenide; water; bromine; diisobutylaluminium hydride; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 7.1: Diels-Alder reaction;

DOI:10.1039/b111446h

upstream raw materials:

(S)-(+)-3,4-dihydro-7,9-dihydroxy-3-methyl-1H-naphtho[2,3-c]pyran-5,10-dione

(S)-mellein

(S)-(+)-7-bromo-3-methyl-3,4-dihydro-1H-2-benzopyran-5,8-dione

(S)-(+)-5,7-dibromo-8-hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran

Refernces

• 1、 Donner, Christopher D.,Gill, Melvyn. "Pigments of fungi. Part 68. Synthesis and absolute configuration of thysanone2". . p. 938 - 948. Retrieved 2002.
• 2、 Sperry, Jonathan,Brimble, Margaret A.. "An efficient enantioselective synthesis of the 3C protease inhibitor (-)-thysanone". scheme or table. p. 1910 - 1912. Retrieved 2009/05/27.