(R)-[(2S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride

Base Information

• Chemical Name: (R)-[(2S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride
• CAS No.: 67174-25-8
• Molecular Formula: C27H31 N2 O2 . Cl
• Molecular Weight: 451.008
• Hs Code.: 29339900
• European Community (EC) Number: 614-029-7
• Mol file: 67174-25-8.mol

Synonyms:N-Benzylquininium chloride;67174-25-8

Chemical Property of (R)-[(2S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride

Chemical Property:

• Melting Point: 200-205oC (dec.)(lit.)
• Refractive Index: 227.5 ° (C=1.5, H2O)
• PSA: 42.35000
• LogP: 1.85100
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 450.2074059
• Heavy Atom Count: 32
• Complexity: 620

Purity/Quality:

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

N-Benzylquininium chloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CC[N+]3(CC4C=C)CC5=CC=CC=C5)O.[Cl-]
• Isomeric SMILES: COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3CC4CC[N+]3(C[C@@H]4C=C)CC5=CC=CC=C5)O.[Cl-]
• Uses: 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.

Technology Process of (R)-[(2S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride

There total 1 articles about (R)-[(2S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;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: 68.0%

benzyl chloride (100-44-7) + Quinine (130-95-0) → (-)-N-benzylquininium chloride (67174-25-8)

Guidance literature:

In acetone; at 60 ℃; for 36h;

DOI:10.1248/cpb.29.1321

Reference yield: 99.0%

4-methoxy-phenol (150-76-5) + (-)-N-benzylquininium chloride (67174-25-8) → N-benzylquininium 4-methoxyphenoxide

Guidance literature:

(-)-N-benzylquininium chloride; With Ion-exchange resin Amberlyst A-26 (OH-); In methanol; at 20 ℃; for 10h; Inert atmosphere; Schlenk technique;

4-methoxy-phenol; In toluene;

DOI:10.1002/adsc.201201041

Reference yield: 40.0%

acetic anhydride (108-24-7) + (-)-N-benzylquininium chloride (67174-25-8) → (-)-O-acetyl-N-benzylquinium chloride (77452-62-1)

Guidance literature:

at 100 ℃; for 0.5h;

DOI:10.1039/P19810000574

upstream raw materials:

benzyl chloride

Quinine

Downstream raw materials:

N-Benzylquininium methoxide

(-)-O-acetyl-N-benzylquinium chloride

Refernces

• 1、 Antien, Kevin,Viault, Guillaume,Pouységu, Laurent,Peixoto, Philippe A.,Quideau, Stéphane. "Asymmetric dearomative spirolactonization of naphthols using λ3-iodanes under chiral phase-transfer catalysis". supporting information. p. 3684 - 3690. Retrieved 2017/06/13.