N-Benzylcinchoninium Chloride [Chiral Phase-Transfer Catalyst] - ≥99% , CAS No.69221-14-3

CAS: 69221-14-3 Cat. No.: B120854 Molecular Weight: 420.98 Beilstein Registry Number: 5232950 EC Number: 273-915-8

GRADE & PURITY ≥99%

Synonyms

B1689 | N-Benzylcinchoninium chloride | (2R,4S,5R)-1-benzyl-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride | EINECS 273-915-8 | SCHEMBL690387 | N-Benzylcinchoninium chloride, 98% | (9S)-1-Benzyl-9-hydroxycinchonanium ch

Storage

Room temperature

Shipped In

Normal

Overview

Phase-transfer catalyst involved in: Enantioselective alkylation of malonic diester with alkyl halides Hydrolysis of enol esters Asymmetric 6π electrocyclization for synthesis of functionalized indolines Asymmetric Michael addition Alkylation of monosubstituted indolinones with alkylhalides Asymmetric destruction and kinetic resolution of 1-benzylated Reissert compounds

Specifications

Synonyms

B1689 | N-Benzylcinchoninium chloride | (2R, 4S, 5R)-1-benzyl-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride | EINECS 273-915-8 | SCHEMBL690387 | N-Benzylcinchoninium chloride, 98% | (9S)-1-Benzyl-9-hydroxycinchonanium ch

Specifications & Purity

≥99%

Storage

Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488197457
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488197457
• Canonical Smiles: C=CC1C[N+]2(CCC1CC2C(C3=CC=NC4=CC=CC=C34)O)CC5=CC=CC=C5.[Cl-]
• IUPAC Name: (S)-[(2R,4S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride
• InChIKey: FCHYSBWCOKEPNQ-YGNISETGSA-M
• 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
• Isomeric SMILES: C=C[C@H]1C[N+]2(CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O)CC5=CC=CC=C5.[Cl-]
• WGK Germany: 3
• Molecular Weight: 420.98
• Beilstein: 5232950
• Reaxy-Rn: 61779607
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=61779607&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Cinchona alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Cinchona alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Cinchona alkaloids
• Alternative Parents: N-benzylpiperidines 4-quinolinemethanols Quinuclidines Benzylamines Phenylmethylamines Aralkylamines Pyridines and derivatives Heteroaromatic compounds Tetraalkylammonium salts 1,2-aminoalcohols Secondary alcohols Azacyclic compounds Organic zwitterions Hydrocarbon derivatives Aromatic alcohols Organic chloride salts
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cinchonan-skeleton - Benzylpiperidine - N-benzylpiperidine - 4-quinolinemethanol - Quinoline - Quinuclidine - Benzylamine - Phenylmethylamine - Aralkylamine - Pyridine - Monocyclic benzene moiety - Piperidine - Benzenoid - Tetraalkylammonium salt - Heteroaromatic compound - Quaternary ammonium salt - 1,2-aminoalcohol - Secondary alcohol - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Aromatic alcohol - Organic zwitterion - Organooxygen compound - Organonitrogen compound - Organic salt - Organic chloride salt - Hydrocarbon derivative - Organic oxygen compound - Amine - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Slightly soluble in Methanol
• Specific Rotation[α]: 168.5° (C=0.4,MeOH:H2O=1:5)
• Melt Point(°C): 256°C
• Molecular Weight: 421.000 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 420.197 Da
• Monoisotopic Mass: 420.197 Da
• Topological Polar Surface Area: 33.100 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 573.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

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