(S)-4-Propylpyrrolidin-2-one
[CAS# 930123-38-9]

Identification

• Name: (S)-4-Propylpyrrolidin-2-one
• Synonyms: (4S)-4-propylpyrrolidin-2-one
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18
• CAS Registry Number: 930123-38-9
• SMILES: CCC[C@H]1CC(=O)NC1

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.443, Calc.^*
• Boiling Point: 263.4±9.0 ºC (760 mmHg), Calc.^*
• Flash Point: 146.8±3.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

(S)-4-Propylpyrrolidin-2-one is a chiral lactam that has attracted much attention in the field of pharmaceutical research and organic synthesis. The synthesis of (S)-4-propylpyrrolidin-2-one (also known as (S)-4-propyl-2-pyrrolidone) was first reported in the late 20th century. Researchers are exploring new chiral lactams to use them as building blocks for drug development and asymmetric synthesis. The compound was synthesized by an enantioselective method, ensuring the production of the desired (S)-enantiomer with high optical purity.

(S)-4-Propylpyrrolidin-2-one, with the chemical formula C7H13NO, is a colorless to pale yellow liquid at room temperature. It has a boiling point of about 215-220°C and is soluble in a variety of organic solvents such as ethanol, methanol, and chloroform. The chiral center at the 4-position of the pyrrolidone ring confers stereochemical specificity to the molecule, which is crucial for its biological activity and interactions in asymmetric synthesis.

One of the major applications of (S)-4-propylpyrrolidin-2-one is in pharmaceutical research. It is a key intermediate in the synthesis of various chiral drugs. The specific configuration of the (S)-enantiomer can be used to develop drugs with targeted biological activity. Compounds derived from this lactam have been investigated for potential use in the treatment of neurological diseases, pain management, and as antimicrobial agents.

In organic synthesis, (S)-4-propylpyrrolidin-2-one is used for enantioselective reactions. Its chirality makes it a valuable starting material or reagent for the production of other chiral molecules with high enantiomeric excess. This is particularly important in the synthesis of complex natural products and active pharmaceutical ingredients (APIs), as stereochemistry plays a key role in biological efficacy.

The compound can also be used to catalyze asymmetric synthesis. It can act as a chiral auxiliary or ligand in various catalytic processes, facilitating the production of enantiomerically pure products. This is crucial in the manufacture of fine chemicals and pharmaceuticals, as chiral purity is a prerequisite.

Recent studies have explored the potential use of (S)-4-propylpyrrolidin-2-one in materials science. Its unique structural properties make it a candidate for the development of new polymers and materials with specific chiral properties. These materials can be used in a variety of applications ranging from enantioselective catalysis to the creation of chiral surfaces and coatings.

Ongoing research continues to discover new applications and improve the efficiency of (S)-4-propylpyrrolidin-2-one in various fields. Innovations in synthetic methods and the development of new chiral technologies are expected to expand its use, providing new opportunities for its application in advanced technologies and medicines.