(3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one

Base Information

• Chemical Name: (3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one
• CAS No.: 143140-06-1
• Molecular Formula: C13H13 N O2
• Molecular Weight: 215.25
• European Community (EC) Number: 630-811-0
• DSSTox Substance ID: DTXSID50428114
• Nikkaji Number: J654.367G
• Wikidata: Q76393788
• Mol file: 143140-06-1.mol

Synonyms:143140-06-1;(3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one;(3S,7aR)-7a-methyl-3-phenyl-2,3-dihydropyrrolo[2,1-b]oxazol-5(7aH)-one;(3S,7aR)-7a-methyl-3-phenyl-2,3-dihydropyrrolo[2,1-b][1,3]oxazol-5-one;(3S-CIS)-(+)-2,3-DIHYDRO-7A-METHYL-3-PHENYLPYRROLO[2,1-B ]OXAZOL-5(7A H)-ONE;SCHEMBL4245370;DTXSID50428114;J-007748;2,3-Dihydro-3alpha-phenyl-7aalpha-methyl-5H-pyrrolo[2,1-b]oxazole-5-one;(3S,7aR)-7a-Methyl-3-phenyl-2,3-dihydropyrrolo[2,1-b][1,3]oxazol-5(7aH)-one;(3s-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7a H)-one;(3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one, 98%

Chemical Property of (3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one

Chemical Property:

• Vapor Pressure: 6.24E-07mmHg at 25°C
• Melting Point: 88-92 °C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 410°Cat760mmHg
• Flash Point: 201.7°C
• PSA: 29.54000
• Density: 1.25g/cm³
• LogP: 1.81040
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 215.094628657
• Heavy Atom Count: 16
• Complexity: 333

Purity/Quality:

95% ^*data from raw suppliers

(3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one 98% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12C=CC(=O)N1C(CO2)C3=CC=CC=C3
• Isomeric SMILES: C[C@@]12C=CC(=O)N1[C@H](CO2)C3=CC=CC=C3
• Uses: High levels of asymmetric induction have been obtained with this chiral bicyclic lactam in cycloadditions, alkylations, conjugate additions, annulations, and dihydroxylations.

Technology Process of (3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one

There total 4 articles about (3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-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:

(3S,7aR)-7a-Methyl-3-phenyl-6-phenylselanyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one → (3S,7aR)-7a-Methyl-3-phenyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one (143140-06-1)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; at 0 ℃; for 12h; Yield given;

DOI:10.1021/jo00119a012

Reference yield:

(2S)-2-phenylglycinol (20989-17-7) → (3S,7aR)-7a-Methyl-3-phenyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one (143140-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / toluene / Heating

In toluene;

DOI:10.1021/jo9600870

Reference yield:

levulinic acid (123-76-2) → (3S,7aR)-7a-Methyl-3-phenyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one (143140-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / toluene / Heating

In toluene;

DOI:10.1021/jo9600870

upstream raw materials:

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

(2S)-2-phenylglycinol

levulinic acid

Refernces

• 1、 Meyers, A. I.,Tschantz, Matt A.,Brengel, Gregory P.. "Asymmetric Lewis Acid-Catalyzed Addition of a Ketene Dithioacetal to a Chiral Bicyclic Lactam. Formation of Cyclobutanopyrrolidinones. A New Class of GABA Derivatives". . p. 4359 - 4362. Retrieved 2007/10/02.