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

• ChemBase ID: 148643
• 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-IOPLZPHGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-1-benzyl-5-ethenyl-2-[(R)-hydroxy(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium chloride
• IUPAC Traditional name: (2S,4S,5R)-1-benzyl-5-ethenyl-2-[(R)-hydroxy(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium chloride
• Synonyms: BCDC; N-Benzylcinchonidinium chloride; (8S,9R)-(-)-N-Benzylcinchonidinium chloride; N-Benzylcinchonidinium chloride; N-苄基氯化辛可尼丁; (8S,9R)-(-)-N-苄基氯化辛可尼丁; N-苄基氯化辛可宁丁

Database IDs

• CAS Number: 69257-04-1
• EC Number: 273-938-3
• MDL Number: MFCD00082422
• Beilstein Number: 5421832
• PubChem SID: 162242818; 24848081; 24862091
• PubChem CID: 10938717

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: 210 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -180°, c = 1.3 in H2O; [α]20/D -188±3°, 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
• 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 - 359580

Other Notes
Chiral phase transfer catalyst1,2;resolutions by crystallization of the inclusion complex3,4
Packaging
10 g in glass bottle

Sigma Aldrich - 13285

Other Notes
Chiral phase transfer catalyst 1,2; resolutions by crystallization of the inclusion complex 3,4