Tanshinol B

Base Information

• Chemical Name: Tanshinol B
• CAS No.: 96839-29-1
• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.323
• DSSTox Substance ID: DTXSID90914288
• Nikkaji Number: J815.999H
• Wikidata: Q82885063
• Mol file: 96839-29-1.mol

Synonyms:przewaquinone C

Chemical Property of Tanshinol B

Chemical Property:

• Vapor Pressure: 2.25E-12mmHg at 25°C
• Boiling Point: 537.3°Cat760mmHg
• Flash Point: 278.7°C
• PSA: 67.51000
• Density: 1.344g/cm³
• LogP: 3.17780
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 296.10485899
• Heavy Atom Count: 22
• Complexity: 515

Purity/Quality:

Analysis control,HPLC≥95% ^*data from raw suppliers

PrzewaquinoneC ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)O

Technology Process of Tanshinol B

There total 5 articles about Tanshinol B 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: 68.0%

4,5-dihydro-3-methylbenzo[1,2-b]furan-4,5-dione (113297-21-5) + 1-methyl-2-vinylcyclohex-2-en-1-ol (124292-44-0) → 6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione (96839-29-1)

Guidance literature:

In methanol; at 45 ℃; for 2h; regioselective reaction; Inert atmosphere; Sonication;

DOI:10.1039/c8ob00567b

Reference yield:

cyclohexenone (930-68-7) → 6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione (96839-29-1)

Guidance literature:

Multi-step reaction with 4 steps

1: iodine; potassium carbonate; dmap / tetrahydrofuran; water / 1 h / 20 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide / tetrahydrofuran / 7 h / -78 - 20 °C

3: diethyl ether / 0.5 h / 0 °C

4: methanol / 2 h / 45 °C / Inert atmosphere; Sonication

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; potassium carbonate; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether; water; 2: |Negishi Coupling / 3: |Grignard Reaction;

DOI:10.1039/c8ob00567b

Reference yield:

2-iodocyclohex-2-en-1-one (33948-36-6) → 6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione (96839-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide / tetrahydrofuran / 7 h / -78 - 20 °C

2: diethyl ether / 0.5 h / 0 °C

3: methanol / 2 h / 45 °C / Inert atmosphere; Sonication

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether; 1: |Negishi Coupling / 2: |Grignard Reaction;

DOI:10.1039/c8ob00567b

upstream raw materials:

cyclohexenone

2-iodocyclohex-2-en-1-one

2-vinylcyclohex-2-en-1-one

4,5-dihydro-3-methylbenzo[1,2-b]furan-4,5-dione

Downstream raw materials:

(+)-(3R,4S)-tanshindiol B

tanshindiol B

(+)-(3S,4S)-tanshindiol C

tanshindiol C

Refernces