2-(4,5-Dihydro-2-oxazolyl)quinoline
Product Information
Molecular Formula
C12H10N2O
Molecular Weight
198.22
Description
2-(4,5-Dihydro-2-oxazolyl)quinoline is a chiral nitrogen ligand for enantioselective synthesis.
Synonyms
2-(2-Quinolinyl)oxazoline, Sigman ligand
IUPAC Name
2-quinolin-2-yl-4,5-dihydro-1,3-oxazole
SMILES
C1(C2=NCCO2)=NC3=CC=CC=C3C=C1
InChI
InChI=1S/C12H10N2O/c1-2-4-10-9(3-1)5-6-11(14-10)12-13-7-8-15-12/h1-6H,7-8H2
InChI Key
USDSJWOYSHFPND-UHFFFAOYSA-N
Flash Point
Not applicable
Purity
≥96.5% (HPLC)
Storage
Inert atmosphere. Keep cold.
Safety Information
Hazards
H315 - H319
Precautionary Statement
P302 + P352 - P305 + P351 + P338
Signal Word
Warning
Computed Properties
XLogP3
2.1
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
198.079312947 g/mol
Monoisotopic Mass
198.079312947 g/mol
Topological Polar Surface Area
34.5Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
264
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2021252492-A1 | Catalyst for contaminant reduction and methods of use thereof | 2020-02-11 |
| PT-109598-B | N- (1,2,3-TRIAZOLMETHIL) -3-HYDROXY-3-ARYLOXINDOLES QUIAL NON-RACEMIC | 2016-08-26 |
| PT-108570-B | TERTIARY 3-HYDROXIOXINDOLE AND 3-ALCOXIOXINDOLE DERIVED COMPOUNDS AS ACETYL CHOLINESTERASE AND BUTYL CHOLINESTERASE INHIBITORS AND PROCESS FOR THEIR OBTAINING | 2015-06-23 |
| TW-I710563-B | Condensed cyclic compound and organic light-emitting device including the same | 2015-03-31 |
| EP-3135670-B1 | Tetracarboxylic dianhydride, polyamic acid, polyimide, methods for producing same, and polyamic acid solution | 2014-04-23 |
| US-2011054176-A1 | Quinoline-oxazoline compounds and their use in oxidation synthesis | 2009-09-03 |
| US-8263774-B2 | Quinoline-oxazoline compounds and their use in oxidation synthesis | 2009-09-03 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22742056 | 2012-07-18 | Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles | Journal of the American Chemical Society |
| 21553838 | 2011-06-01 | On the mechanism of the palladium-catalyzed tert-butylhydroperoxide-mediated Wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands | Journal of the American Chemical Society |
| 21446720 | 2011-05-06 | Catalyst-controlled Wacker-type oxidation of homoallylic alcohols in the absence of protecting groups | The Journal of organic chemistry |
| 21200719 | 2007-12-06 | 2-(4,5-Dihydro-1,3-oxazol-2-yl)quinoline | Acta crystallographica. Section E, Structure reports online |
