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Merck
CN

650897

(4S,4′S)-(−)-2,2′-(3-Pentylidene)bis(4-isopropyloxazoline)

97%

Synonym(s):

(4S,4′S)-(−)-2,2′-(1-Ethylpropylidene)bis(4,5-dihydro-4-isopropyloxazole), [S-(R*,R*)]-(−)-2,2′-(1-Ethylpropylidene)bis(4,5-dihydro-4-isopropyloxazole)

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About This Item

Empirical Formula (Hill Notation):
C17H30N2O2
CAS Number:
160191-65-1
Molecular Weight:
294.43
NACRES:
NA.22
PubChem Substance ID:
24883790
UNSPSC Code:
12352005
MDL number:
MFCD03427142

Key Documents

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InChI

1S/C17H30N2O2/c1-7-17(8-2,15-18-13(9-20-15)11(3)4)16-19-14(10-21-16)12(5)6/h11-14H,7-10H2,1-6H3/t13-,14-/m1/s1

SMILES string

CCC(CC)(C1=N[C@H](CO1)C(C)C)C2=N[C@H](CO2)C(C)C

InChI key

PIJFQTUSLZLNOP-ZIAGYGMSSA-N

assay

97%

refractive index

n20/D 1.4710 (lit.)

bp

120 °C/0.001 mmHg (lit.)

density

1.002 g/mL at 25 °C (lit.)

functional group

ether

Quality Level

100

Related Categories

Application

(4S,4′S)-(−)-2,2′-(3-Pentylidene)bis(4-isopropyloxazoline) is a bisoxazoline that can be used as a ligand:
  • To prepare [11C]carboxylic acids, [11C]esters and [11C]amides using boronic acid esters and 11CO2.
  • In one of the key synthetic steps for the total synthesis of tatanan A and 3-epi-tatanan A.
  • To prepare copper(I) complex and used in a mass spectrometric method to study its chiral selectivity with different substrates.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

180.0 °F - closed cup

flash_point_c

82.22 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT1367
MKCJ9941
MKCF3810
MKCF2611
MKBT2292V

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CuI-catalyzed 11C carboxylation of boronic acid esters: A rapid and convenient entry to 11C-labeled carboxylic acids, esters, and amides
Riss PJ, et al.
Angewandte Chemie (International ed. in English), 51(11), 2698-2702 (2012)
Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis
Noble A, et al.
Angewandte Chemie (International ed. in English), 55(51), 15920-15924 (2016)
A mass spectrometric method for rapidly assaying the chiral selectivities of the copper (I) complexes of C2-symmetric ligands.
Davis MC and Gronert S.
Journal of Mass Spectrometry : Jms, 50(11), 1279-1287 (2015)

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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