1,2-Dihydrotanshinquinone

Base Information

• Chemical Name: 1,2-Dihydrotanshinquinone
• CAS No.: 77769-21-2
• Molecular Formula: C₁₈H₁₄O₃
• Molecular Weight: 278.307
• DSSTox Substance ID: DTXSID60998959
• Nikkaji Number: J2.764.613A,J323.571H
• Wikidata: Q82991780
• Metabolomics Workbench ID: 124972
• ChEMBL ID: CHEMBL1813349
• Mol file: 77769-21-2.mol

Synonyms:1,2-dihydrotanshinquinone;1,2-DT-quinone;dan-shen root extract;Danshen extract;danshen root extract;methylenetanshinquinone;Salvia miltiorrhiza root;tanshinquinone, methylene-

Chemical Property of 1,2-Dihydrotanshinquinone

Chemical Property:

• Vapor Pressure: 5.81E-10mmHg at 25°C
• Refractive Index: 1.629
• Boiling Point: 495.6 °C at 760 mmHg
• Flash Point: 244.6 °C
• PSA: 47.28000
• Density: 1.286 g/cm³
• LogP: 3.98350
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 278.094294304
• Heavy Atom Count: 21
• Complexity: 521

Purity/Quality:

99% ^*data from raw suppliers

1,2-Dihydrotanshinquinone ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CCCC2=C1C=CC3=C2C(=O)C(=O)C4=C3OC=C4C

Technology Process of 1,2-Dihydrotanshinquinone

There total 7 articles about 1,2-Dihydrotanshinquinone 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%

6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione (96839-29-1) → 1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione (77769-21-2)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 80 ℃; for 1h;

DOI:10.1039/c8ob00567b

Reference yield:

cyclohexenone (930-68-7) → 1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione (77769-21-2)

Guidance literature:

Multi-step reaction with 5 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

5: toluene-4-sulfonic acid / methanol / 1 h / 80 °C

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; potassium carbonate; toluene-4-sulfonic acid; 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) → 1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione (77769-21-2)

Guidance literature:

Multi-step reaction with 4 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

4: toluene-4-sulfonic acid / methanol / 1 h / 80 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; toluene-4-sulfonic acid; 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

1-methyl-2-vinylcyclohex-2-en-1-ol

Downstream raw materials:

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

tanshindiol B

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

tanshindiol C

Refernces