1-Cyano-cyclopentanoic acid-1-carboxylic acid
Basic Information
· Chinese name: 1-Cyanocyclopentane-1-carboxylic acid
· English name: 1-Cyanocyclopentane-1-carboxylic acid
· CAS number: 540490-54-8
· Molecular formula: C₇H₉NO₂
· Molecular weight: 139.15 g/mol
Chemical structure
This is a cyclic compound that contains both cyano and carboxy functional groups. Its core structure is a five-membered ring (cyclopentane), with a cyano group and a carboxy group connected to the same carbon atom.
The structural formula can be expressed as:
```
O
∥ HO-C-CN
|
(CH₂)₄
```
Or, more precisely, it can be described as a cyclopentane in which one of the carbon atoms is simultaneously substituted by both -COOH and -CN.
Chemical properties
1. Bifunctional groups: This is the most important characteristic of this molecule. It possesses:
· Carboxylic acid: It is acidic and can form salts, esters, amides, etc.
· Cyanide group: It can act as a potential amine precursor (through reduction), or be converted into another carboxylic acid under hydrolysis conditions, generating 1,1-cyclopentane dicarboxylic acid.
2. Acidity: Due to the presence of the carboxyl group, it is an organic acid, with a pKa value typically ranging from 4 to 5.
3. Stability: This molecule is usually stable at normal temperature and pressure, but it should be avoided from coming into contact with strong oxidants, strong bases or strong acids under intense conditions, as cyanide groups may undergo unnecessary reactions.
Main purpose
1-Cyano-cyclopentane-1-carboxylic acid is mainly used as a key building block in organic synthesis, especially in the research and production of medicines and pesticides.
· Pharmaceutical intermediates:
· Core application: It is a key starting material or intermediate for synthesizing CGRP receptor antagonists, which are crucial drugs for treating and preventing migraines.
· Specific drugs: It is used to synthesize existing highly effective migraine treatment drugs such as Atogepant and Rimegepant. In the molecular structures of these drugs, the 1-cyanocyclopentan-1-carboxylic acid fragment constitutes part of the core pharmacophore.
· Other potential applications: Due to its unique rigid cyclic structure and dual functional groups, it is also often used to construct complex molecules with specific three-dimensional structures, which may be used in the development of other neurological drugs or protease inhibitors.
· Pesticide intermediates: As an intermediate for synthesizing certain compounds with specific biological activities.
· High molecular materials: May be used to synthesize monomers or polymers with special properties.
Safety Information
· GHS Hazard Classification: The specific classification depends on the assessment by the supplier, but it usually may include:
· Acute Toxicity: It may be harmful if ingested, inhaled, or absorbed through the skin.
· Skin Corrosion/ Irritation: It may cause skin irritation.
· Severe Eye Damage/Irritation: It may cause eye irritation.
· Operating Precautions:
· Operations should be carried out in a well-ventilated area to avoid the formation of dust and aerosols.
· Wear appropriate protective clothing, gloves, and goggles/face masks.
· Due to the presence of cyano groups, extra caution is required during handling to avoid inhalation and skin contact. Although its toxicity is usually much lower than inorganic cyanides, it still needs to be treated with caution.
· Storage: Store in a sealed container in a dry, cool place, away from incompatible substances.
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In summary, 1-cyano-cyclopentane-1-carboxylic acid is a highly valuable pharmaceutical intermediate with a unique structure and specific application. It plays an indispensable role in the synthesis of modern innovative drugs, especially those for treating migraines.
