Циклопентилпропионилхлорид, with the CAS number 104-97-2, is a highly valuable chemical intermediate widely used in organic synthesis, pharmaceutical manufacturing, and specialty chemical production. This compound, also known as 3-cyclopentylpropionyl chloride or cyclopentanepropionyl chloride, belongs to the class of acyl chlorides and serves as an essential building block for numerous chemical transformations.

With the molecular formula C8H13ClO and a molecular weight of 160.64 g/mol, this compound features a cyclopentane ring attached to a propionyl chloride chain. This unique structure provides distinctive reactivity patterns that make it indispensable in modern chemical manufacturing.

What Is Cyclopentylpropionyl Chloride?

Cyclopentylpropionyl chloride is an organic compound with the systematic name 3-cyclopentylpropanoyl chloride. It appears as a colorless to light yellow liquid with a pungent, characteristic odor typical of acyl chlorides. The compound is also known by several synonyms:

• 3-Cyclopentylpropionyl chloride
• Cyclopentanepropionyl chloride
• 3-Cyclopentylpropanoyl chloride
• C5H9CH2CH2COCl

The compound’s linear formula is C5H9CH2CH2COCl, and its SMILES notation is ClC(=O)CCC1CCCC1. This acyl chloride is classified under EC number 203-257-9 and has a Beilstein/REAXYS number of 1856952.

What Are the Benefits?

Versatile Chemical Intermediate

One of the primary benefits of cyclopentylpropionyl chloride is its versatility as a chemical intermediate. The compound’s dual functionality—the cyclopentyl ring and the acyl chloride group—allows for numerous chemical transformations, making it an excellent building block for synthesizing more complex molecules.

Pharmaceutical Applications

In drug development, cyclopentylpropionyl chloride can be used to synthesize intermediates for antibacterial or anti-inflammatory drugs featuring a cyclopentane core. The cyclopentane structure provides a unique molecular geometry that is valuable in optimizing the activity of drug molecules.

Enzyme Inhibitor Synthesis

3-Cyclopentylpropionyl chloride serves as a synthetic intermediate in the synthesis of a new family of type 3 17β-Hydroxysteroid dehydrogenase inhibitors. These enzymes are important targets in various therapeutic areas, making this compound valuable in pharmaceutical research and development.

Boronic Acid Derivative Synthesis

The compound has been used in the synthesis of 3-cyclopentylpropanamidomethylboronic acid, a compound of interest in medicinal chemistry research. Boronic acid derivatives often exhibit unique biological activities and are valuable in drug discovery programs.

What Are the Uses?

Pharmaceutical Manufacturing

Cyclopentylpropionyl chloride is primarily used in pharmaceutical manufacturing as an intermediate in the synthesis of various drug compounds:

• Synthesis of enzyme inhibitors
• Development of anti-inflammatory agents
• Production of antibacterial compounds
• Research on steroid hormone modulators

Fragrance and Flavor Industry

In fragrance synthesis, 3-cyclopentylpropionyl chloride can introduce cyclopentyl structures via acylation, enhancing the longevity of fragrances. This application leverages the compound’s ability to create interesting molecular architectures in aromatic compounds.

Organic Synthesis Research

In research laboratories, cyclopentylpropionyl chloride serves as a valuable reagent for:

• Amide bond formation
• Ester synthesis
• Ketone preparation
• Various acylation reactions

Agrochemical Development

The compound is also used in the development of agrochemical intermediates, contributing to the synthesis of novel crop protection agents and plant growth regulators.

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