(S)-[(2R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride

Base Information

• Chemical Name: (S)-[(2R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride
• CAS No.: 69221-14-3
• Molecular Formula: C26H29ClN2O
• Molecular Weight: 420.982
• Hs Code.: 29339900
• European Community (EC) Number: 273-915-8
• Mol file: 69221-14-3.mol

Synonyms:69221-14-3;N-Benzylcinchoninium chloride;N-BENZYLCINCHONINIUMCHLORIDE

Chemical Property of (S)-[(2R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride

Chemical Property:

• Melting Point: 256 °C (dec.)(lit.)
• Refractive Index: 168.5 ° (C=0.4, MeOH:H2O=1:5)
• PSA: 33.12000
• LogP: 1.84240
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: slightly sol. in Methanol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 420.1968412
• Heavy Atom Count: 30
• Complexity: 573

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Benzylcinchoninium chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CC1C[N+]2(CCC1CC2C(C3=CC=NC4=CC=CC=C34)O)CC5=CC=CC=C5.[Cl-]
• Isomeric SMILES: C=CC1C[N+]2(CCC1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O)CC5=CC=CC=C5.[Cl-]
• Uses: Phase-transfer catalyst involved in:Enantioselective alkylation of malonic diester with alkyl halidesHydrolysis of enol estersAsymmetric 6π electrocyclization for synthesis of functionalized indolinesAsymmetric Michael additionAlkylation of monosubstituted indolinones with alkylhalidesAsymmetric destruction and kinetic resolution of 1-benzylated Reissert compounds

Technology Process of (S)-[(2R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride

There total 2 articles about (S)-[(2R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzyl chloride (100-44-7) + Cinchonidin (485-71-2) → N1-benzylcinchonidinium chloride (69221-14-3,69257-04-1,95189-65-4)

Guidance literature:

In toluene; for 2h; Reflux;

Reference yield: 95.0%

benzyl chloride (100-44-7) + Cinchonin (118-10-5) → (9S)-9-hydroxy-1-(phenylmethyl)-cinchonanium chloride (69221-14-3)

Guidance literature:

In ethanol; chloroform; N,N-dimethyl-formamide; at 100 ℃; for 10h;

DOI:10.1002/cjoc.201200598

Reference yield: 99.0%

N1-benzylcinchonidinium chloride (69221-14-3,69257-04-1,95189-65-4) + methyl iodide (74-88-4) → C27H31N2O(1+)*I(1-)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tet.2017.04.028

upstream raw materials:

benzyl chloride

Cinchonin

Cinchonidin

Downstream raw materials:

N-Benzylcinchoninium methoxide

Ethanolate(1S,2R,4S,5R)-1-benzyl-2-((S)-hydroxy-quinolin-4-yl-methyl)-5-vinyl-1-azonia-bicyclo[2.2.2]octane;

(S)-[1,1']-binaphthalenyl-2,2'-diol

N-9-benzylcinchonidinium p-vinylbenzoate

Refernces

• 1、 Zhang, Tao,Scalabrino, Gaia,Frankish, Neil,Sheridan, Helen. "Bioactive indanes: Proof of concept study for enantioselective synthetic routes to ph46a, a new potential anti-inflammatory agent". . . Retrieved 2018/07/10.
• 2、 Wang, Yang,Sun, Jie,Ding, Kuiling. "Practical method and novel mechanism for optical resolution of BINOL by molecular complexation with N-benzylcinchoninium chloride". . p. 4447 - 4451. Retrieved 2007/10/03.