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Sigma-Aldrich

N-[(1R,2R)-2-(1-Piperidinyl)cyclohexyl]-N′-[4-(trifluoromethyl)phenyl]squaramide

95%

Synonym(s):

3-{[(1R,2R)-2-(1-Piperidinyl)cyclohexyl]amino}-4-{[4-(trifluoromethyl)phenyl]amino}-3-cyclobutene-1,2-dione, Rawal Squaramide Organocatalyst

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$170.00
500 MG
$240.00

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100 MG
$170.00
500 MG
$240.00

About This Item

Empirical Formula (Hill Notation):
C22H26F3N3O2
CAS Number:
1211565-08-0
Molecular Weight:
421.46
MDL number:
MFCD18827464
UNSPSC Code:
12352005
PubChem Substance ID:
329764393
NACRES:
NA.22

$170.00

In StockDetails

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Quality Level

100

assay

≥94.5% (HPLC)
95%

form

powder

optical activity

[α]/D -42.0±2.0°, c = 1 in DMSO

impurities

≤2.0% pyridine

functional group

fluoro
ketone

SMILES string

FC(F)(F)c1ccc(NC2=C(N[C@@H]3CCCC[C@H]3N4CCCCC4)C(=O)C2=O)cc1

InChI

1S/C22H26F3N3O2/c23-22(24,25)14-8-10-15(11-9-14)26-18-19(21(30)20(18)29)27-16-6-2-3-7-17(16)28-12-4-1-5-13-28/h8-11,16-17,26-27H,1-7,12-13H2/t16-,17-/m1/s1

InChI key

JRSCPJJNZMRAQS-IAGOWNOFSA-N

Application

Catalyst for enantioselective Michael addition[1].
It can act as a catalyst for the asymmetric tandem aza-Michael addition-protonation between 1-nitro cyclohexene and 4-methoxyaniline to form the corresponding α-arylamino-β-nitro cyclohexane in a 35:65 trans/cis mixture.[2]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW6370
BCBC6462V
BCBC6462

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Squaramide-catalyzed enantioselective Michael addition of diphenyl phosphite to nitroalkenes.
Ye Zhu et al.
Angewandte Chemie (International ed. in English), 49(1), 153-156 (2009-12-02)
Stereoselective aza-Michael addition of anilines to 1-nitro cyclohexene by intramolecular protonation.
Ghisu L, et al.
Tetrahedron Letters, 56(46), 6409-6412 (2015)

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