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728357

Sigma-Aldrich

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

95%

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Synonym(s):
3-{[(1R,2R)-2-(1-Piperidinyl)cyclohexyl]amino}-4-{[4-(trifluoromethyl)phenyl]amino}-3-cyclobutene-1,2-dione, Rawal Squaramide Organocatalyst
Empirical Formula (Hill Notation):
C22H26F3N3O2
CAS Number:
1211565-08-0
Molecular Weight:
421.46
MDL number:
MFCD18827464
PubChem Substance ID:
329764393
NACRES:
NA.22

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

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

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70751193956765880
N-[(1R,2R)-2-(1-Piperidinyl)cyclohexyl]-N′-[4-(trifluoromethyl)phenyl]squaramide 95%

Sigma-Aldrich

728357

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

(1R,2R)-(+)-N,N′-Dimethyl-1,2-bis[3-(trifluoromethyl)phenyl]ethanediamine 97%

Sigma-Aldrich

707511

(1R,2R)-(+)-N,N′-Dimethyl-1,2-bis[3-(trifluoromethyl)phenyl]ethanediamine

4-(Trifluoromethyl)-D-phenylalanine ≥98.5% (HPLC)

Sigma-Aldrich

93956

4-(Trifluoromethyl)-D-phenylalanine

4-Amino-2-(trifluoromethyl)pyridine 97%

Sigma-Aldrich

765880

4-Amino-2-(trifluoromethyl)pyridine

form

powder

form

powder

form

powder

form

solid

optical activity

[α]/D -42.0±2.0°, c = 1 in DMSO

optical activity

[α]22/D +18.0°, c = 1 in chloroform

optical activity

-

optical activity

-

impurities

≤2.0% pyridine

impurities

-

impurities

-

impurities

-

Application

Catalyst for enantioselective Michael addition.
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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315 - H318 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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