4H-1-Benzothiopyran-4-one, 2,3-dihydro-2-phenyl-, 1-oxide

Base Information

• Chemical Name: 4H-1-Benzothiopyran-4-one, 2,3-dihydro-2-phenyl-, 1-oxide
• CAS No.: 58109-92-5
• Molecular Formula: C15H12O2S
• Molecular Weight: 256.325
• DSSTox Substance ID: DTXSID50450990
• Nikkaji Number: J600.646I
• Mol file: 58109-92-5.mol

Synonyms:1-Thioflavanone 1-oxide;58109-92-5;4H-1-Benzothiopyran-4-one, 2,3-dihydro-2-phenyl-, 1-oxide;DTXSID50450990

Chemical Property of 4H-1-Benzothiopyran-4-one, 2,3-dihydro-2-phenyl-, 1-oxide

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 256.05580079
• Heavy Atom Count: 18
• Complexity: 346

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(S(=O)C2=CC=CC=C2C1=O)C3=CC=CC=C3

Technology Process of 4H-1-Benzothiopyran-4-one, 2,3-dihydro-2-phenyl-, 1-oxide

There total 6 articles about 4H-1-Benzothiopyran-4-one, 2,3-dihydro-2-phenyl-, 1-oxide 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: 76.0%

2-phenyl-thiochroman-4-one (5962-00-5,110318-31-5) → 2-phenylthiochroman-4-one 1-oxide (58109-92-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02977

Reference yield:

2-aminoacetophenone (551-93-9) → 2-phenylthiochroman-4-one 1-oxide (58109-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / acetonitrile

1.2: 2 h / 0 - 20 °C

2.1: sodium hydroxide / ethanol; water / 6 h / 0 - 20 °C

3.1: potassium ethyl xanthogenate; copper diacetate / dimethyl sulfoxide / 6 h / 70 °C

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere

With copper diacetate; potassium ethyl xanthogenate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/acs.orglett.5b02977

Reference yield:

(E)-1-(2-iodophenyl)-3-phenylprop-2-en-1-one (107921-63-1) → 2-phenylthiochroman-4-one 1-oxide (58109-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: copper diacetate / toluene / 70 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere

With copper diacetate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;

DOI:10.1021/acs.orglett.5b02977

upstream raw materials:

2-phenyl-thiochroman-4-one

(E)-1-(2-iodophenyl)-3-phenylprop-2-en-1-one

(E)-1-(2-bromophenyl)-3-phenylprop-2-en-1-one

2-aminoacetophenone

Downstream raw materials:

2-(phenylmethylene)benzothiophen-3(2H)-one

1-thioflavone

1-thioflavone 1-oxide