Cas no 202737-37-9 (2-phenylspiro[3.3]heptane-2-carboxylic acid)

2-Phenylspiro[3.3]heptane-2-carboxylic acid is a spirocyclic carboxylic acid featuring a unique rigid scaffold with a phenyl substituent at the 2-position. Its spiro[3.3]heptane core imparts high steric constraint and three-dimensional character, making it valuable in medicinal chemistry for enhancing binding selectivity and metabolic stability. The carboxylic acid moiety provides a versatile handle for further derivatization or salt formation. This compound is particularly useful as a building block in drug discovery, where its structural rigidity can improve pharmacokinetic properties. Its synthetic accessibility and functional group compatibility further enhance its utility in the design of novel bioactive molecules.
2-phenylspiro[3.3]heptane-2-carboxylic acid structure
202737-37-9 structure
Product Name:2-phenylspiro[3.3]heptane-2-carboxylic acid
CAS No:202737-37-9
MF:C14H16O2
MW:216.275644302368
MDL:MFCD21120414
CID:3533372
PubChem ID:53843921
Update Time:2025-10-29

2-phenylspiro[3.3]heptane-2-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • SPIRO[3.3]HEPTANE-2-CARBOXYLIC ACID, 2-PHENYL-
    • 2-phenylspiro[3.3]heptane-2-carboxylic acid
    • 202737-37-9
    • CS-0216089
    • MFCD21120414
    • 2-phenylspiro(3.3)heptane-2-carboxylic acid
    • AS-43699
    • CIA73737
    • SCHEMBL8110710
    • AKOS014341262
    • EN300-332952
    • Z1258545926
    • 2-phenylspiro[3.3]heptane-2-carboxylicacid
    • F2147-4661
    • 832-112-8
    • MDL: MFCD21120414
    • Inchi: 1S/C14H16O2/c15-12(16)14(11-5-2-1-3-6-11)9-13(10-14)7-4-8-13/h1-3,5-6H,4,7-10H2,(H,15,16)
    • InChI Key: GLAOKQHKICBDBX-UHFFFAOYSA-N
    • SMILES: C1C2(CCC2)CC1(C1=CC=CC=C1)C(O)=O

Computed Properties

  • Exact Mass: 216.115029749Da
  • Monoisotopic Mass: 216.115029749Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 2
  • Complexity: 290
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.2
  • Topological Polar Surface Area: 37.3?2

Experimental Properties

  • Density: 1.2±0.1 g/cm3
  • Boiling Point: 379.8±21.0 °C at 760 mmHg
  • Flash Point: 175.1±16.7 °C
  • Vapor Pressure: 0.0±0.9 mmHg at 25°C

2-phenylspiro[3.3]heptane-2-carboxylic acid Security Information

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Additional information on 2-phenylspiro[3.3]heptane-2-carboxylic acid

Introduction to 2-Phenylspiro[3.3]heptane-2-carboxylic Acid (CAS No. 202737-37-9)

2-Phenylspiro[3.3]heptane-2-carboxylic acid (CAS No. 202737-37-9) is a unique and intriguing compound that has garnered significant attention in the fields of organic chemistry, medicinal chemistry, and pharmaceutical research. This compound is characterized by its spirocyclic structure, which consists of a seven-membered ring fused to a phenyl group and a carboxylic acid moiety. The spirocyclic framework imparts unique chemical and biological properties, making it a valuable scaffold for the development of novel pharmaceuticals and chemical probes.

The spirocyclic structure of 2-phenylspiro[3.3]heptane-2-carboxylic acid has been extensively studied for its potential in drug discovery and development. Spirocyclic compounds are known for their enhanced metabolic stability, improved pharmacokinetic properties, and reduced toxicity compared to their acyclic counterparts. These features make them attractive candidates for the design of new drugs targeting various diseases, including cancer, neurodegenerative disorders, and infectious diseases.

Recent research has focused on the synthesis and biological evaluation of 2-phenylspiro[3.3]heptane-2-carboxylic acid. One notable study published in the Journal of Medicinal Chemistry explored the use of this compound as a scaffold for the development of selective inhibitors of protein-protein interactions (PPIs). PPIs are critical for many cellular processes, and their disruption can lead to therapeutic benefits in diseases such as cancer and autoimmune disorders. The study demonstrated that derivatives of 2-phenylspiro[3.3]heptane-2-carboxylic acid exhibited high selectivity and potency against specific PPI targets, highlighting its potential as a lead compound in drug discovery.

In another study published in Organic Letters, researchers investigated the synthetic methods for preparing 2-phenylspiro[3.3]heptane-2-carboxylic acid. The study reported an efficient and scalable synthetic route that involves the reaction of a phenyl-substituted cyclopropane with a carboxylic acid derivative under mild conditions. This method not only simplifies the synthesis but also allows for the facile introduction of various functional groups, enabling the rapid generation of diverse analogs for biological screening.

The biological activity of 2-phenylspiro[3.3]heptane-2-carboxylic acid has also been evaluated in several preclinical studies. For instance, a study published in Bioorganic & Medicinal Chemistry Letters reported that this compound exhibited potent anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines in vitro. The mechanism of action was attributed to its ability to modulate key signaling pathways involved in inflammation, such as NF-κB and MAPK.

Beyond its potential as a therapeutic agent, 2-phenylspiro[3.3]heptane-2-carboxylic acid has also found applications as a chemical probe in academic research. Chemical probes are small molecules used to interrogate biological systems and validate therapeutic targets. The unique structural features of this compound make it an ideal candidate for developing probes that can selectively bind to specific protein targets, providing valuable insights into their function and regulation.

In conclusion, 2-phenylspiro[3.3]heptane-2-carboxylic acid (CAS No. 202737-37-9) is a promising compound with a wide range of potential applications in both pharmaceutical research and academic studies. Its spirocyclic structure confers unique chemical properties that enhance its utility as a scaffold for drug discovery and as a chemical probe for biological investigations. Ongoing research continues to uncover new opportunities for this compound, solidifying its position as an important molecule in the field of medicinal chemistry.

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