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54060

Sigma-Aldrich

Hydrocinchonine

≥95.0% (sum of enantiomers, HPLC)

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Synonym(s):
Dihydrocinchonine
Empirical Formula (Hill Notation):
C19H24N2O
CAS Number:
485-65-4
Molecular Weight:
296.41
Beilstein:
4296749
EC Number:
207-621-8
MDL number:
MFCD00216716
UNSPSC Code:
12352005
PubChem Substance ID:
57651461
NACRES:
NA.22

Quality Level

100

Assay

≥95.0% (sum of enantiomers, HPLC)
≥97.0% (NT)

optical activity

[α]20/D +197±4°, c = 0.25% in ethanol

mp

269-272 °C (lit.)

SMILES string

CC[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c3ccnc4ccccc34

InChI

1S/C19H24N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h3-7,9,13-14,18-19,22H,2,8,10-12H2,1H3/t13-,14-,18+,19-/m0/s1

InChI key

WFJNHVWTKZUUTR-QAMTZSDWSA-N

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Application

Hydrocinchonine is an alkaloid that can be used as a chiral base in:
  • The 1,3-dipolar cycloaddition reactions of alkenes and azomethine ylides using silver fluoride.
  • The aza-Henry reaction for the synthesis of molecules with optically active quaternary centers.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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A convenient procedure for the catalytic asymmetric 1, 3-dipolar cycloaddition of azomethine ylides and alkenes
Alemparte C, et al.
Organic Letters, 7(21), 4569-4572 (2005)
A chiral molecular recognition approach to the formation of optically active quaternary centres in aza-Henry reactions
Knudsen KR and Jorgensen KA
Organic & Biomolecular Chemistry, 3(8), 1362-1364 (2005)

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