Cas no 859689-01-3 (1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester)

1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester is a cyclopropane derivative with a monoethyl ester functional group, offering a reactive intermediate for synthetic organic chemistry applications. Its strained cyclopropane ring enhances reactivity, making it valuable for ring-opening reactions and cycloadditions. The presence of the 2,2-dimethyl substituents provides steric hindrance, influencing selectivity in transformations. The monoethyl ester group allows for further functionalization, such as hydrolysis or transesterification, enabling versatility in fine chemical synthesis. This compound is particularly useful in pharmaceutical and agrochemical research, where cyclopropane motifs are sought after for their bioactivity and structural rigidity. Its stability under standard conditions ensures ease of handling in laboratory settings.
1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester structure
859689-01-3 structure
Product Name:1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester
CAS No:859689-01-3
MF:C9H14O4
MW:186.205063343048
CID:582831
PubChem ID:25198090
Update Time:2025-05-21

1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester Chemical and Physical Properties

Names and Identifiers

    • 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester
    • 1-ethoxycarbonyl-2,2-dimethylcyclopropane-1-carboxylate
    • EN300-8131277
    • 1-(Ethoxycarbonyl)-2,2-dimethylcyclopropane-1-carboxylic acid
    • SCHEMBL5107238
    • 859689-01-3
    • Inchi: 1S/C9H14O4/c1-4-13-7(12)9(6(10)11)5-8(9,2)3/h4-5H2,1-3H3,(H,10,11)
    • InChI Key: BNESMMDYENMHDL-UHFFFAOYSA-N
    • SMILES: O(CC)C(C1(C(=O)O)CC1(C)C)=O

Computed Properties

  • Exact Mass: 186.08920892g/mol
  • Monoisotopic Mass: 186.08920892g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 4
  • Complexity: 256
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.4
  • Topological Polar Surface Area: 63.6?2

1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester Pricemore >>

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Additional information on 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester

Recent Advances in the Study of 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester (CAS: 859689-01-3)

The compound 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester (CAS: 859689-01-3) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This molecule, characterized by its cyclopropane ring and dicarboxylic acid derivatives, serves as a versatile intermediate in the synthesis of various bioactive compounds. Recent studies have explored its potential applications in drug discovery, particularly in the development of enzyme inhibitors and small-molecule therapeutics.

One of the key areas of research focuses on the role of this compound in the synthesis of cyclopropane-containing drugs, which are known for their unique pharmacological properties. Cyclopropane rings are often incorporated into drug molecules to enhance metabolic stability and binding affinity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester exhibit promising inhibitory activity against certain proteases involved in inflammatory pathways. The study utilized molecular docking and kinetic assays to validate these findings, highlighting the compound's potential as a scaffold for anti-inflammatory drug development.

Another significant advancement involves the use of this compound in asymmetric synthesis. Researchers have developed novel catalytic methods to enantioselectively modify the monoethyl ester group, enabling the production of chiral intermediates with high optical purity. This breakthrough, reported in Angewandte Chemie, has broad implications for the synthesis of stereochemically complex pharmaceuticals. The study also emphasized the compound's compatibility with green chemistry principles, as the reactions were conducted under mild conditions with minimal waste generation.

In addition to its synthetic utility, 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester has been investigated for its biological activity. A preclinical study published in Bioorganic & Medicinal Chemistry Letters revealed that certain analogs of this compound exhibit moderate antimicrobial activity against Gram-positive bacteria. The researchers attributed this effect to the compound's ability to disrupt bacterial cell wall synthesis, suggesting its potential as a lead structure for novel antibiotics. Further optimization of these analogs is currently underway to improve their potency and pharmacokinetic properties.

Despite these promising developments, challenges remain in the large-scale production and application of this compound. Recent patents filed by pharmaceutical companies indicate ongoing efforts to optimize synthetic routes and improve yield. For instance, a 2023 patent application by Merck & Co. describes a scalable, cost-effective method for producing high-purity 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester using continuous flow chemistry. This innovation could facilitate its broader adoption in industrial drug manufacturing.

In conclusion, 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, monoethyl ester (CAS: 859689-01-3) represents a valuable building block in medicinal chemistry with diverse applications. Its role in the synthesis of bioactive molecules, coupled with its emerging biological activities, underscores its importance in current research. Future studies are expected to further elucidate its mechanisms of action and explore its potential in treating various diseases, positioning it as a key player in the next generation of pharmaceutical innovations.

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