7,8-Dihydroquinolin-5(6H)-one

Base Information

• Chemical Name: 7,8-Dihydroquinolin-5(6H)-one
• CAS No.: 53400-41-2
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 2933499090
• European Community (EC) Number: 692-491-9
• DSSTox Substance ID: DTXSID70201567
• Nikkaji Number: J89.779E
• Wikidata: Q72506914
• ChEMBL ID: CHEMBL3586000
• Mol file: 53400-41-2.mol

Synonyms:53400-41-2;7,8-Dihydroquinolin-5(6H)-one;7,8-dihydro-6H-quinolin-5-one;5,6,7,8-Tetrahydroquinolinone-5;5,6,7,8-Tetrahydro-5-quinolinone;5,6,7,8-Tetrahydroquinolin-5-one;7,8-Dihydro-5(6H)-quinolinone;5(6H)-Quinolinone, 7,8-dihydro-;MFCD02181161;5-Oxo-5,6,7,8-tetrahydroquinoline;4,5,6,7,8-tetrahydro-5-quinolinone;7,8-Dihydro-5(6H)-quinolone;7,8-dihydroquinoline-5(6H)-one;SCHEMBL936485;5,6,7,8-Tetrahydroquinolinone;7,8-Dihydro-5(6H)quinolinone;CHEMBL3586000;AMY9700;DTXSID70201567;7,8-Dihydro-5-(6H)quinolinone;YHHBKPWMEXGLKE-UHFFFAOYSA-N;AKOS000280639;CCG-321318;PB30737;PS-3961;SY042025;BB 0260763;CS-0006841;D5877;FT-0649781;EN300-81910;A829566;F9995-1281;Z1201621685

Chemical Property of 7,8-Dihydroquinolin-5(6H)-one

Chemical Property:

• Vapor Pressure: 0.00731mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 269.3 °C at 760 mmHg
• PKA: 3.85±0.20(Predicted)
• Flash Point: 123.8 °C
• PSA: 29.96000
• Density: 1.168 g/cm³
• LogP: 1.60060
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

98%, ^*data from raw suppliers

7,8-Dihydro-5(6H)-quinolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=CC=N2)C(=O)C1
• Uses: 7,8-Dihydro-5(6H)-quinolone is used as a reagent in the synthesis of pyridino N-alkylated nicotine analogs which can serve as nicotinic acetylcholine receptor antagonists. 7,8-Dihydro-5(6H)-quinolone is also used in the total synthesis of (±)-tangutorine, a novel indole alkaloid.

Technology Process of 7,8-Dihydroquinolin-5(6H)-one

There total 4 articles about 7,8-Dihydroquinolin-5(6H)-one 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: 52.5%

1-(pyridin-3-yl)cyclobutanol (87549-96-0) → 6, 7-dihydro-5H-isoquinolin-8-one (21917-88-4) + 5,6,7,8-tetrahydroquinolin-5-one (53400-41-2)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.166667h;

DOI:10.1021/acs.orglett.8b03246 DOI:10.1021/acs.orglett.8b03246

Reference yield:

→ 5,6,7,8-tetrahydroquinoline (10500-57-9) + 5,6,7,8-tetrahydroquinolin-5-one (53400-41-2)

Guidance literature:

Reference yield:

1,3-dioxoisoindolin-2-yl 5-oxo-5-(pyridin-3-yl)pentanoate → 6, 7-dihydro-5H-isoquinolin-8-one (21917-88-4) + 5,6,7,8-tetrahydroquinolin-5-one (53400-41-2)

Guidance literature:

With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; trifluoroacetic acid; In dimethyl sulfoxide; at 20 ℃; for 5h; Overall yield = 54percent; Overall yield = 40 mg; Irradiation;

DOI:10.1021/acs.joc.9b00432

upstream raw materials:

1-(pyridin-3-yl)cyclobutanol

5-oxo-5-(pyridin-3-yl)pentanoic acid

Downstream raw materials:

5-phenyl-5,6,7,8-tetrahydro-quinolin-5-ol

(+)-<5S>-5-hydroxy-5,6,7,8-tetrahydroquinoline

(R)-5,6,7,8-tetrahydroquinolin-5-ol

Refernces

• 1、 Fang, Jingxian,Li, Lesong,Yang, Chu,Chen, Jinping,Deng, Guo-Jun,Gong, Hang. "Tandem Oxidative Ring-Opening/Cyclization Reaction in Seconds in Open Atmosphere for the Synthesis of 1-Tetralones in Water-Acetonitrile". supporting information. . Retrieved 2018/11/23.
• 2、 -. "Certain 5,6,7,8-tetrahydroquinoline-8-thiocarboxamides". . . Retrieved 2008/06/13.