N-Benzylquininium Chloride [Chiral Phase-Transfer Catalyst] - ≥95% , CAS No.67174-25-8

CAS: 67174-25-8 Cat. No.: B120850 Molecular Weight: 451.01 Beilstein Registry Number: 5702637 EC Number: 614-029-7 PubChem CID: 10863314

GRADE & PURITY ≥95%

Synonyms

SCHEMBL306470 | (1S,2S,4S,5R)-1-benzyl-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride | (2S,4S,5R)-1-Benzyl-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride | N-Benzylquininium ch

Storage

Room temperature

Shipped In

Normal

Overview

N-Benzylquininium chloride (or Quibec) belongs to the class of cinchona family of alkaloids. It is used as a catalyst in the presence of hydroxide bases in various phase transfer reactions, epoxidations, alkylations, and Michael reactions.

Application：

N-Benzylquininium chloride can be used as a phase transfer catalyst:

In the sulfenylation of various β-keto sulfoxides.

To synthesize N-carbamoyl-protected β-nitroamines from α-amido sulfones by asymmetric aza-Henry reaction.

Specifications

Synonyms

SCHEMBL306470 | (1S, 2S, 4S, 5R)-1-benzyl-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride | (2S, 4S, 5R)-1-Benzyl-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride | N-Benzylquininium ch

Specifications & Purity

≥95%

Storage

Room temperature

Shipped In

Normal

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 488196866
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488196866
• Canonical Smiles: COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CC[N+]3(CC4C=C)CC5=CC=CC=C5)O.[Cl-]
• IUPAC Name: (R)-[(1S,2S,4S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride
• InChIKey: JYDIJFKNXHPWBJ-GOGFHWEMSA-M
• INCHI: 1S/C27H31N2O2.ClH/c1-3-20-18-29(17-19-7-5-4-6-8-19)14-12-21(20)15-26(29)27(30)23-11-13-28-25-10-9-22(31-2)16-24(23)25;/h3-11,13,16,20-21,26-27,30H,1,12,14-15,17-18H2,2H3;1H/q+1;/p-1/t20-,21-,26-,27+,29+;/m0./s1
• Isomeric SMILES: COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CC[N@+]3(C[C@@H]4C=C)CC5=CC=CC=C5)O.[Cl-]
• WGK Germany: 3
• PubChem CID: 10863314
• Molecular Weight: 451.01
• Beilstein: 5702637
• Reaxy-Rn: 14541607

Chemical and Physical Properties

• Specific Rotation[α]: 227.5° (C=1.5,H2O)
• Melt Point(°C): 200-205 °C (dec.) (lit.)