(R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one

Base Information

• Chemical Name: (R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one
• CAS No.: 173140-90-4
• Molecular Formula: C18H15NO3
• Molecular Weight: 293.322
• Hs Code.: 2933790090
• European Community (EC) Number: 478-690-1,691-332-0
• DSSTox Substance ID: DTXSID90465922
• Wikidata: Q72498490
• Mol file: 173140-90-4.mol

Synonyms:173140-90-4;(R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one;5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone;2(1H)-Quinolinone, 5-(2R)-oxiranyl-8-(phenylmethoxy)-;5-[(2R)-oxiran-2-yl]-8-phenylmethoxy-1H-quinolin-2-one;8-(Benzyloxy)-5-[(2R)-oxiran-2-yl]quinolin-2(1H)-one;8-(benzyloxy)-5-[(2R)-oxiran-2-yl]-1,2-dihydroquinolin-2-one;IHJYYLJZVBVLEK-INIZCTEOSA-N;SCHEMBL866306;DTXSID90465922;MFCD17018704;(r)-8-benzyloxy-5-oxiranylcarbostyril;AKOS015999467;AC-30183;AS-70020;CS-0047675;5-(2R)-2-Oxiranyl-8-(phenylmethoxy)-2(1H)-quinolinone

Chemical Property of (R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one

Chemical Property:

• Boiling Point: 556.0±50.0 °C(Predicted)
• PKA: 10.92±0.70(Predicted)
• PSA: 54.62000
• Density: 1.298
• LogP: 3.17840
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 293.10519334
• Heavy Atom Count: 22
• Complexity: 444

Purity/Quality:

99.9% ^*data from raw suppliers

(R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)C2=C3C=CC(=O)NC3=C(C=C2)OCC4=CC=CC=C4
• Isomeric SMILES: C1[C@H](O1)C2=C3C=CC(=O)NC3=C(C=C2)OCC4=CC=CC=C4
• Uses: 5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone is used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Technology Process of (R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one

There total 10 articles about (R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-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:

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (100331-89-3) → (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone (173140-90-4)

Guidance literature:

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 0 - 2 ℃; for 1.75h;

With piperidine; water; In tetrahydrofuran; toluene; at 0 - 2 ℃; for 1h; Product distribution / selectivity;

Reference yield:

8-(phenylmethoxy)-5-((R)-2-chloro-1-hydroxy-ethyl)-(1H)-quinolin-2-one → (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone (173140-90-4)

Guidance literature:

With potassium carbonate; In water; acetone; for 5 - 10h; Heating / reflux;

Reference yield:

8-quinolinol (148-24-3,24804-14-6) → (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone (173140-90-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1,2-dichloro-ethane / 2.25 - 2.33 h / 30 °C

1.2: 15.25 - 16.33 h / 25 - 70 °C

1.3: 0.25 - 0.33 h / 0 - 30 °C

2.1: hydrogenchloride; water / 0.25 - 0.33 h

3.1: potassium carbonate / acetone / 14 h / Heating / reflux

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C

5.1: acetic anhydride / 2 h / 25 - 40 °C

6.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux

6.2: 4.5 h / Heating / reflux

6.3: 30 °C / pH 8 - 9

7.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C

7.2: 1 h / 0 - 2 °C

With hydrogenchloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; water; acetic anhydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetone; toluene;

upstream raw materials:

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

8-quinolinol

5-acetyl-8-hydroxyquinoline

Downstream raw materials:

8-benzyloxy-5-{(1R)-1-hydroxy-2-[N-((1R)-2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril

8-benzyloxy-5-{(1R)-1-hydroxy-2-[N-((lR)-2-(p-methoxy phenyl)-1-methylethyl) amino] ethyl} carbostyril hydrochloride

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-dimethylindan-2-ylamino)-ethyl]-1H-quinolin-2-one

(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one

Refernces

• 1、 -. "ORGANIC COMPOUNDS". Page/Page column 36. . Retrieved 2008/06/13.
• 2、 -. "PROCESS FOR PREPARING 5-'(R)-2-(5,6-DIETHYL-INDIAN-2-YLAMINO)-1-HYDROXY-ETHYL!-8-HYDROXY-(1H)-QUINOLIN-2-ONE SALT, USEFUL AS AN ADRENOCEPTOR AGONIST". Page/Page column 22. . Retrieved 2008/06/13.