Quinuclidinyl benzilate, (+)-

Base Information

• Chemical Name: Quinuclidinyl benzilate, (+)-
• CAS No.: 62869-68-5
• Molecular Formula: C21H23NO3
• Molecular Weight: 337.419
• UNII: VH47AP03H6
• DSSTox Substance ID: DTXSID00863910
• Nikkaji Number: J419.450K
• Wikidata: Q27291832
• ChEMBL ID: CHEMBL1788199
• Mol file: 62869-68-5.mol

Synonyms:(S)-3-Quinuclidinyl benzilate;(+)-3-Quinuclidinyl benzilate;(S)-(+)-Qnb;Quinuclidinyl benzilate, (+)-;UNII-VH47AP03H6;VH47AP03H6;(+)-quinuclidinyl benzilate;62869-68-5;CHEMBL1788199;Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, (3S)-1-azabicyclo(2.2.2)oct-3-yl ester;L-QUINUCLIDINYL BENZILATE;DTXSID00863910;BDBM50367742;QUINUCLIDINYL BENZILATE, (S)-;Q27291832;BENZENEACETIC ACID, .ALPHA.-HYDROXY-.ALPHA.-PHENYL-, (3S)-1-AZABICYCLO(2.2.2)OCT-3-YL ESTER;BENZENEACETIC ACID, .ALPHA.-HYDROXY-.ALPHA.-PHENYL-, 1-AZABICYCLO(2.2.2)OCT-3-YL ESTER, (S)-

Chemical Property of Quinuclidinyl benzilate, (+)-

Chemical Property:

• PSA: 49.77000
• LogP: 2.49780
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 337.16779360
• Heavy Atom Count: 25
• Complexity: 442

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O
• Isomeric SMILES: C1CN2CCC1[C@@H](C2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O

Technology Process of Quinuclidinyl benzilate, (+)-

There total 2 articles about Quinuclidinyl benzilate, (+)- 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: 33.0%

(S)-3-quinuclidinol (34583-34-1) + Benzilic acid (76-93-7) → (S)-3-(1-azabicyclo<2.2.2>octyl) α-hydroxy-α,α-diphenylacetate (62869-68-5)

Guidance literature:

Benzilic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 - 80 ℃; for 0.5h;

(S)-3-quinuclidinol; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1002/jlcr.460

Reference yield:

(S)-quinuclidin-3-ol (3684-26-2,25333-42-0,34583-34-1,1619-34-7) + ethyl benzilate (52182-15-7) → (S)-3-(1-azabicyclo<2.2.2>octyl) α-hydroxy-α,α-diphenylacetate (62869-68-5)

Guidance literature:

With sodium; Yield given. Multistep reaction; 1) benzene, 30 min, reflux; 2) benzene, reflux, 30 min;

DOI:10.1021/jm00402a035

Reference yield: 95.0%

(S)-3-(1-azabicyclo<2.2.2>octyl) α-hydroxy-α,α-diphenylacetate (62869-68-5) + methyl iodide (74-88-4) → N-methyl-quinuclidin-3-yl benzilate, iodide salt

Guidance literature:

In 1,4-dioxane; for 1h;

DOI:10.1002/jlcr.460

upstream raw materials:

(S)-quinuclidin-3-ol

ethyl benzilate

(S)-3-quinuclidinol

Benzilic acid