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Merck
CN

406961

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline]

97%

Synonym(s):

(R,R)-2,2′-Bis(4-phenyl-2-oxazolin-2-yl)propane, (R,R)-2,2′-Isopropylidenebis(4-phenyl-2-oxazoline)

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About This Item

Empirical Formula (Hill Notation):
C21H22N2O2
CAS Number:
150529-93-4
Molecular Weight:
334.41
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24865413
MDL number:
MFCD00192244
Beilstein/REAXYS Number:
4266906

Key Documents

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Product Name

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline], 97%

InChI

1S/C21H22N2O2/c1-21(2,19-22-17(13-24-19)15-9-5-3-6-10-15)20-23-18(14-25-20)16-11-7-4-8-12-16/h3-12,17-18H,13-14H2,1-2H3/t17-,18-/m0/s1

SMILES string

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

InChI key

JTNVCJCSECAMLD-ROUUACIJSA-N

assay

97%

form

solid

optical activity

[α]20/D +160°, c = 1 in ethanol

mp

56-58 °C (lit.)

functional group

ether
phenyl

storage temp.

−20°C

Quality Level

100

Related Categories

Application

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline] in the presence of copper iodide, can catalyze the asymmetric cyclopropanation reaction of phenyliodonium ylides with alkenes to form cyclopropane α-amino acid esters.
C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

wgk

WGK 3

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT0676
MKCL9891
MKCF0437
MKBS0620V
MKBQ3477V

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Benoît Moreau et al.
Journal of the American Chemical Society, 127(51), 18014-18015 (2005-12-22)
A highly enantioselective (up to 97.5% ee) and diastereoselective (95:5 dr trans/cis) Cu(I)-catalyzed cyclopropanation of alkenes using phenyliodonium ylide generated in situ from iodosobenzene and methyl nitroacetate is reported. The cyclopropanation took place with high enantioselectivity for a wide range
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)
Bolm, C.
Angewandte Chemie (International Edition in English), 30, 542-542 (1991)
Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)

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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