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Merck
CN

417068

(4S)-(+)-Phenyl-α-[(4S)-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile

97%

Synonym(s):

(S,S)-4-Phenyl-α-(4-phenyloxazolidin-2-ylidene)-2-oxazoline-2-acetonitrile

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About This Item

Empirical Formula (Hill Notation):
C20H17N3O2
CAS Number:
150639-33-1
Molecular Weight:
331.37
NACRES:
NA.22
PubChem Substance ID:
24866118
UNSPSC Code:
12352005
MDL number:
MFCD00192394

Key Documents

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Product Name

(4S)-(+)-Phenyl-α-[(4S)-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile, 97%

InChI

1S/C20H17N3O2/c21-11-16(19-22-17(12-24-19)14-7-3-1-4-8-14)20-23-18(13-25-20)15-9-5-2-6-10-15/h1-10,17-18,22H,12-13H2/b19-16-/t17-,18-/m1/s1

SMILES string

N#C\C(=C1\N[C@H](CO1)c2ccccc2)C3=N[C@H](CO3)c4ccccc4

InChI key

QVVGSAYHUSBCQV-SRKGJJLTSA-N

assay

97%

form

solid

optical activity

[α]20/D +364°, c = 1 in chloroform

mp

146-148 °C (lit.)

functional group

ether
nitrile
phenyl

Quality Level

200

Related Categories

Application

(4S)-(+)-Phenyl-α-[(4S)-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile/Re(V)-oxo complex can catalyze the asymmetric hydrosilylation of ketones.
Ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

General description

(4S)-(+)-Phenyl-α-[(4S)-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile is a C2-symmetric chiral bisoxazoline (BOX) ligand.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000205998
0000151836
0000151836
0000205998
0000177447

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Enantioselective Reduction of Ketones and Imines Catalyzed by (CN-Box) ReV-Oxo Complexes.
Nolin KA, et al.
Chemistry?A European Journal , 16(31), 9555-9562 (2010)
Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)
Bolm, C.
Angewandte Chemie (International Edition in English), 30, 542-542 (1991)

Articles

C2-symmetric chiral bisoxazolines (BOX) ligands

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

C2型轴对称手性双噁唑啉（BOX）配体

使用络合Cu(I)OTf的BOX配体进行不对称催化苯乙烯合成氮杂环丙烷的反应，BOX配体带苯基取代基的优于具有位阻需求的叔丁(t-Bu)基团。

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