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406961

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

Name: (+)-2,2′-Isopropylidenebis[(4<I>R</I>)-4-phenyl-2-oxazoline]
Brand: ALDRICH

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

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Properties

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

SMILES string

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

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

InChI key

JTNVCJCSECAMLD-ROUUACIJSA-N

Description

Application

C₂ symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

(+)-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.

wgk

WGK 3

pictograms

GHS06

signalword

Danger

hcodes

H301 + H311 + H331

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

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

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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。

Expedient synthesis of cyclopropane alpha-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate.

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

Pfaltz, A.

Accounts of Chemical Research, 26, 339-339 (1993)

Bolm, C.

Angewandte Chemie (International Edition in English), 30, 542-542 (1991)

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Global Trade Item Number

SKU	GTIN
406961-250MG	04061833055199
406961-1G	04061826732618