1-Azoniabicyclo[2.2.2]octane-3-carboxylate

Base Information

• Chemical Name: 1-Azoniabicyclo[2.2.2]octane-3-carboxylate
• CAS No.: 75208-40-1
• Molecular Formula: C8H13 N O2
• Molecular Weight: 155.197
• Hs Code.: 2933990090
• Mol file: 75208-40-1.mol

Synonyms:1-azoniabicyclo[2.2.2]octane-3-carboxylate;STL036786;AKOS005690655

Chemical Property of 1-Azoniabicyclo[2.2.2]octane-3-carboxylate

Chemical Property:

• Vapor Pressure: 0.000769mmHg at 25°C
• Boiling Point: 284.5°C at 760 mmHg
• Flash Point: 125.9°C
• PSA: 40.54000
• Density: 1.23g/cm³
• LogP: 0.35070
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 155.094628657
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

98%Min ^*data from raw suppliers

3-QuinuclidinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C[NH+]2CCC1C(C2)C(=O)[O-]
• Uses: 3-Quinuclidinecarboxylic Acid is used as phosphodiesterase 4 inhibitors and muscarinic M3 receptor antagonists for treating respiratory tract diseases.

Technology Process of 1-Azoniabicyclo[2.2.2]octane-3-carboxylate

There total 4 articles about 1-Azoniabicyclo[2.2.2]octane-3-carboxylate 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%

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → quinuclidine-3-carboxylic acid (75208-40-1)

Guidance literature:

With water; for 3h; Heating;

DOI:10.1007/BF00532080

Reference yield:

3-Quinuclidinone (3731-38-2) → quinuclidine-3-carboxylic acid (75208-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / t-BuOK, EtOH / 1,2-dimethoxy-ethane / 1.) 5-10 deg C, 0.5 h, 2.) 40 deg C, 2.5 h

2: concd HCl / 3 h / Heating

With hydrogenchloride; ethanol; potassium tert-butylate; In 1,2-dimethoxyethane;

DOI:10.1021/jm00113a009

Reference yield:

3-Cyano-1-azabicyclo[2.2.2]octane (51627-76-0) → quinuclidine-3-carboxylic acid (75208-40-1)

Guidance literature:

With hydrogenchloride; for 3h; Heating;

DOI:10.1021/jm00113a009

upstream raw materials:

3-Cyano-1-azabicyclo[2.2.2]octane

3-quinuclidinecarboxylic acid ethyl ester

3-Quinuclidinone

Downstream raw materials:

3-hydroxymethyl-1-azabicyclo[2.2.2]octane

(3R)-1-azabicyclo[2.2.2]octan-3-ylmethanol

[(3S)-quinuclidin-3-yl]methanol

sabcomeline

Refernces

• 1、 Bromidge, Steven M.,Brown, Frank,Cassidy, Frederick,Clark, Michael S. G.,Dabbs, Steven,Hadley, Michael S.,Hawkins, Julie,Loudon, Julia M.,Naylor, Christopher B.,Orlek, Barry S.,Riley, Graham J.. "Design of [R-(Z)]-(+)-α-(methoxyimino)-1-azabicyclo[2.2.2]octane-3- acetonitrile (SB 202026), a functionally selective azabicyclic muscarinic M1 agonist incorporating the N-methoxy imidoyl nitrile group as a novel ester bioisostere". . p. 4265 - 4280. Retrieved 2007/10/03.
• 2、 Orlek, Barry S.,Blaney, Frank E.,Brown, Frank,Clark, Michael S. G.,Hadley, Michael S.,et al.. "Comparison of Azabicyclic Esters and Oxadiazoles as Ligands for the Muscarinic Receptor". . p. 2726 - 2735. Retrieved 2007/10/02.