Cas no 1157137-71-7 (2-(thiophen-3-yl)cyclopropane-1-carboxylic acid)

2-(Thiophen-3-yl)cyclopropane-1-carboxylic acid is a heterocyclic carboxylic acid derivative featuring a cyclopropane ring fused to a thiophene moiety. This compound is of interest in medicinal chemistry and materials science due to its unique structural framework, which combines the rigidity of the cyclopropane ring with the electronic properties of the thiophene heterocycle. Its carboxylic acid functional group enhances versatility for further derivatization, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, or functional materials. The compound's stability and well-defined reactivity profile facilitate its use in cross-coupling reactions, cycloadditions, and other transformations. Its structural motifs are often explored for their potential bioactivity or optoelectronic applications.
2-(thiophen-3-yl)cyclopropane-1-carboxylic acid structure
1157137-71-7 structure
Product Name:2-(thiophen-3-yl)cyclopropane-1-carboxylic acid
CAS No:1157137-71-7
MF:C8H8O2S
MW:168.212921142578
CID:5215606
PubChem ID:21691177
Update Time:2025-06-08

2-(thiophen-3-yl)cyclopropane-1-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 2-(Thiophen-3-yl)cyclopropane-1-carboxylic acid
    • 2-(Thiophen-3-yl)cyclopropane-1-carboxylicacid
    • Cyclopropanecarboxylic acid, 2-(3-thienyl)-
    • 2-(thiophen-3-yl)cyclopropane-1-carboxylic acid
    • Inchi: 1S/C8H8O2S/c9-8(10)7-3-6(7)5-1-2-11-4-5/h1-2,4,6-7H,3H2,(H,9,10)
    • InChI Key: ZZCJDGURVYEFFD-UHFFFAOYSA-N
    • SMILES: S1C=CC(=C1)C1CC1C(=O)O

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 181
  • XLogP3: 1.3
  • Topological Polar Surface Area: 65.5

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Additional information on 2-(thiophen-3-yl)cyclopropane-1-carboxylic acid

Introduction to 2-(thiophen-3-yl)cyclopropane-1-carboxylic acid (CAS No. 1157137-71-7)

2-(thiophen-3-yl)cyclopropane-1-carboxylic acid, identified by the Chemical Abstracts Service Number (CAS No.) 1157137-71-7, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the class of heterocyclic derivatives, featuring a cyclopropane ring conjugated with a thiophene moiety, which endows it with unique chemical and biological properties. The structural configuration of this molecule makes it a promising candidate for further exploration in drug discovery and development.

The thiophen-3-yl substituent in the molecular structure plays a crucial role in modulating the pharmacological activity of the compound. Thiophene derivatives are well-known for their broad spectrum of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The incorporation of a thiophene ring into a cyclopropane scaffold introduces additional reactivity and binding potential, which can be exploited to design novel therapeutic agents.

In recent years, there has been a growing interest in cyclopropane-containing compounds due to their distinctive pharmacokinetic and pharmacodynamic profiles. The three-membered cyclopropane ring is known to enhance the lipophilicity and metabolic stability of molecules, making them more suitable for oral administration and prolonged biological activity. Additionally, the strain present in the cyclopropane ring can facilitate facile ring-opening reactions, which can be harnessed to develop prodrugs or bioconjugates with enhanced bioavailability.

2-(thiophen-3-yl)cyclopropane-1-carboxylic acid has been studied as a key intermediate in the synthesis of various pharmacologically active compounds. Its structural features make it an attractive building block for designing molecules that target specific biological pathways. For instance, researchers have explored its potential as a precursor in the development of kinase inhibitors, which are critical in treating cancers and inflammatory diseases. The thiophene moiety can interact with metal ions or other biomolecules, while the carboxylic acid group provides a site for further functionalization, such as esterification or amidation.

One of the most compelling aspects of this compound is its role in medicinal chemistry innovation. The combination of a cyclopropane ring and a thiophene substituent creates a scaffold that can be readily modified to optimize drug-like properties such as solubility, permeability, and binding affinity. Recent studies have demonstrated that derivatives of 2-(thiophen-3-yl)cyclopropane-1-carboxylic acid exhibit promising activity against various disease models. For example, modifications to the thiophene ring have led to compounds with enhanced efficacy in inhibiting bacterial enzymes responsible for antibiotic resistance.

The synthetic pathways for 2-(thiophen-3-yl)cyclopropane-1-carboxylic acid have also been refined to improve yield and scalability. Modern synthetic techniques, including transition metal-catalyzed cross-coupling reactions and asymmetric hydrogenation, have enabled the efficient construction of complex derivatives. These advancements have not only facilitated academic research but also paved the way for industrial applications in drug manufacturing.

In addition to its pharmaceutical applications, this compound has shown potential in material science and agrochemical research. The unique electronic properties of the thiophene-cyclopropane system make it suitable for developing organic semiconductors or conductive polymers. Furthermore, its structural motifs have inspired novel pesticides and herbicides with improved environmental profiles.

The future directions of research on 2-(thiophen-3-yl)cyclopropane-1-carboxylic acid are vast and multifaceted. Ongoing studies aim to uncover new biological activities by exploring different substituents on the thiophene ring or by incorporating additional functional groups into the cyclopropane moiety. Computational modeling and high-throughput screening techniques are being employed to accelerate the discovery process.

Collaborative efforts between academia and industry are essential to translate laboratory findings into clinical applications. The development of novel drugs requires interdisciplinary approaches that integrate synthetic chemistry, computational biology, and preclinical testing. 2-(thiophen-3-yl)cyclopropane-1-carboxylic acid serves as a testament to the importance of fundamental research in driving innovation across multiple scientific domains.

In conclusion, 2-(thiophen-3-yl)cyclopropane-1-carboxylic acid (CAS No. 1157137-71-7) is a versatile compound with significant potential in pharmaceuticals, materials science, and agrochemicals. Its unique structural features and modifiable chemical properties make it an invaluable tool for researchers seeking to develop next-generation therapeutics and materials. As our understanding of molecular interactions continues to evolve, compounds like this will play an increasingly critical role in addressing global health challenges.

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