(6aR,11aR)-6a,11a-Dihydro-3,9-dimethoxy-6H-benzofuro[3,2-c][1]benzopyran-8-ol

Base Information

• Chemical Name: (6aR,11aR)-6a,11a-Dihydro-3,9-dimethoxy-6H-benzofuro[3,2-c][1]benzopyran-8-ol
• CAS No.: 108335-31-5
• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.311
• DSSTox Substance ID: DTXSID401140540
• Mol file: 108335-31-5.mol

Synonyms:DTXSID401140540;(6aR,11aR)-6a,11a-Dihydro-3,9-dimethoxy-6H-benzofuro[3,2-c][1]benzopyran-8-ol;108335-31-5

Chemical Property of (6aR,11aR)-6a,11a-Dihydro-3,9-dimethoxy-6H-benzofuro[3,2-c][1]benzopyran-8-ol

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 300.09977361
• Heavy Atom Count: 22
• Complexity: 403

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C3C(CO2)C4=CC(=C(C=C4O3)OC)O
• Isomeric SMILES: COC1=CC2=C(C=C1)[C@H]3[C@@H](CO2)C4=CC(=C(C=C4O3)OC)O

Technology Process of (6aR,11aR)-6a,11a-Dihydro-3,9-dimethoxy-6H-benzofuro[3,2-c][1]benzopyran-8-ol

There total 8 articles about (6aR,11aR)-6a,11a-Dihydro-3,9-dimethoxy-6H-benzofuro[3,2-c][1]benzopyran-8-ol 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: 84.0%

2H-chromene (254-04-6) + 2-methoxy-1,4-benzoquinone (2880-58-2) → (6aS,6bR,10aS,10bR)-9-Methoxy-6a,6b,10a,10b-tetrahydro-6H-5-oxa-benzo[a]biphenylene-7,10-dione (123373-13-7,134453-32-0) + rac-(6aR,11aR)-8-hydroxy-3,9-dimethoxypterocarpan (108335-31-5,123410-69-5,152611-67-1)

Guidance literature:

titanium(IV) isopropylate; titanium tetrachloride; In dichloromethane; at -78 ℃; for 3h; Yields of byproduct given;

DOI:10.1039/C39890000454

Reference yield: 80.0%

(6aS,6bR,10aS,10bR)-3,9-Dimethoxy-6a,6b,10a,10b-tetrahydro-6H-5-oxa-benzo[a]biphenylene-7,10-dione (123389-71-9) → rac-(6aR,11aR)-8-hydroxy-3,9-dimethoxypterocarpan (108335-31-5,123410-69-5,152611-67-1)

Guidance literature:

toluene-4-sulfonic acid; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00291a027

Reference yield: 75.0%

3-chromene (18385-89-2) + 2-methoxy-1,4-benzoquinone (2880-58-2) → rac-(6aR,11aR)-8-hydroxy-3,9-dimethoxypterocarpan (108335-31-5,123410-69-5,152611-67-1)

Guidance literature:

2-methoxy-1,4-benzoquinone; With zinc(II) chloride; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

3-chromene; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/bkcs.11375

upstream raw materials:

2H-chromene

2-methoxy-1,4-benzoquinone

3-chromene

(6aS,6bR,10aS,10bR)-3,9-Dimethoxy-6a,6b,10a,10b-tetrahydro-6H-5-oxa-benzo[a]biphenylene-7,10-dione