3-Phenyltetrahydropyrrolo[2,1-b][1,3]oxazol-5(6H)-one

Base Information

• Chemical Name: 3-Phenyltetrahydropyrrolo[2,1-b][1,3]oxazol-5(6H)-one
• CAS No.: 122383-34-0
• Molecular Formula: C12H13 N O2
• Molecular Weight: 203.24
• DSSTox Substance ID: DTXSID30924149
• Wikidata: Q82898288
• Mol file: 122383-34-0.mol

Synonyms:DTXSID30924149;3-Phenyltetrahydropyrrolo[2,1-b][1,3]oxazol-5(6H)-one

Chemical Property of 3-Phenyltetrahydropyrrolo[2,1-b][1,3]oxazol-5(6H)-one

Chemical Property:

• Vapor Pressure: 4.47E-06mmHg at 25°C
• Melting Point: 76-80 °C
• Refractive Index: 1.5260 (estimate)
• Boiling Point: 383.2°Cat760mmHg
• Flash Point: 185.6°C
• PSA: 29.54000
• Density: 1.25g/cm³
• LogP: 1.64430
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 203.094628657
• Heavy Atom Count: 15
• Complexity: 260

Purity/Quality:

99% ^*data from raw suppliers

(3S,CIS)-(-)-3-PHENYLTETRAHYDROPYRROLO-[2,1-B]-OXAZOL-5(6H)-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N2C1OCC2C3=CC=CC=C3
• Isomeric SMILES: C1CC(=O)N2[C@H]1OC[C@@H]2C3=CC=CC=C3

Technology Process of 3-Phenyltetrahydropyrrolo[2,1-b][1,3]oxazol-5(6H)-one

There total 9 articles about 3-Phenyltetrahydropyrrolo[2,1-b][1,3]oxazol-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: 96.0%

5-Ethoxy-1-((S)-2-hydroxy-1-phenyl-ethyl)-pyrrolidin-2-one (122383-40-8,122383-44-2) → (3S,7aR)-5-oxo-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole (122383-34-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1021/jo00278a053

Reference yield: 72.0%

(S)-N-allyl-N-(2-hydroxy-1-phenylethyl)acrylamide (1311275-81-6) → (3S,7aR)-5-oxo-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole (122383-34-0)

Guidance literature:

With Hoveyda-Grubbs catalyst first generation; In m-xylene; for 18h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201100417

Reference yield:

D-2-phenylglycinol (56613-80-0) → (3S,7aR)-5-oxo-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole (122383-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) triethylamine / 1.) toluene, reflux, 1 h, 2.) reflux, 17 h

2: NaBH₄, 2 M HCl / 3 h / Ambient temperature; pH 1-3

With hydrogenchloride; sodium tetrahydroborate; triethylamine;

DOI:10.1021/jo00278a053

upstream raw materials:

ethanol

(S)-(+)-N-(1-phenyl-2-hydroxyethyl)succinimide

5-Ethoxy-1-((S)-2-hydroxy-1-phenyl-ethyl)-pyrrolidin-2-one

D-2-phenylglycinol

Downstream raw materials:

(3S,6R,7aR)-6-Allyl-6-methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

(3S,6S,7aR)-6-Methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

(3S,7aR)-3-Phenyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one

(3S,7aR)-6-Chloro-3-phenyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one