(2R,4S,5R)-1-benzyl-5-ethenyl-2-[(S)-hydroxy(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium chloride

• ChemBase ID: 151410
• Molecular Formular: C26H29ClN2O
• Molecular Mass: 420.97426
• Monoisotopic Mass: 420.19684124
• SMILES: C=C[C@H]1C[N+]2(CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O)Cc1ccccc1.[Cl-]
• Canonical SMILES: C=C[C@H]1C[N+]2(CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O)Cc1ccccc1.[Cl-]
• InChI: InChI=1S/C26H29N2O.ClH/c1-2-20-18-28(17-19-8-4-3-5-9-19)15-13-21(20)16-25(28)26(29)23-12-14-27-24-11-7-6-10-22(23)24;/h2-12,14,20-21,25-26,29H,1,13,15-18H2;1H/q+1;/p-1/t20-,21-,25+,26-,28?;/m0./s1
• InChIKey: FCHYSBWCOKEPNQ-YGNISETGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R)-1-benzyl-5-ethenyl-2-[(S)-hydroxy(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium chloride
• IUPAC Traditional name: (2R,4S,5R)-1-benzyl-5-ethenyl-2-[(S)-hydroxy(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium chloride
• Synonyms: 9-Hydroxy-1-(phenylmethyl)cinchonanium chloride; BCNC; N-Benzylcinchoninium chloride; N-苄基氯化辛可宁

Database IDs

• CAS Number: 69221-14-3
• EC Number: 273-915-8
• MDL Number: MFCD00082423
• Beilstein Number: 5232950
• PubChem SID: 24862625; 162245564; 24848082
• PubChem CID: 11384639

CALCULATED PROPERTIES

• Acid pKa: 12.609214
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.20532867
• LogD (pH = 7.4): 0.23295832
• Log P: 0.23327172
• Molar Refractivity: 128.7566 cm^3
• Polarizability: 47.272324 Å^3
• Polar Surface Area: 33.12 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 256 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +169±3°, c = 0.4% in H2O; [α]20/D +169°, c = 0.4 in H2O

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (AT); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C26H29ClN2O

DETAILS

Sigma Aldrich - 366188

Packaging
10 g in glass bottle
Application
Phase-transfer catalyst involved in:
• Enantioselective alkylation of malonic diester with alkyl halides1
• Hydrolysis of enol esters2
• Asymmetric 6π electrocyclization for synthesis of functionalized indolines3
• Asymmetric Michael addition4
• Alkylation of monosubstituted indolinones with alkylhalides5
• Asymmetric destruction and kinetic resolution of 1-benzylated Reissert compounds6

Sigma Aldrich - 13288

Other Notes
Chiral phase transfer catalyst7,8,9,10
Application
Phase-transfer catalyst involved in:
• Enantioselective alkylation of malonic diester with alkyl halides1
• Hydrolysis of enol esters2
• Asymmetric 6π electrocyclization for synthesis of functionalized indolines3
• Asymmetric Michael addition4
• Alkylation of monosubstituted indolinones with alkylhalides5
• Asymmetric destruction and kinetic resolution of 1-benzylated Reissert compounds6