Cas no 204378-97-2 (trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid)

Technical Introduction: trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid trans-2-Cyclohexyl-cyclopropyl-1-boronic acid is a specialized boronic acid derivative featuring a cyclohexyl-substituted cyclopropane ring. This compound is valuable in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, due to its stable boronic acid functionality and sterically defined structure. The trans-configuration of the cyclohexyl and cyclopropyl groups enhances its selectivity in forming C-C bonds, making it useful for constructing complex molecular architectures. Its robust stability under typical reaction conditions and compatibility with diverse substrates further underscore its utility in pharmaceutical and materials research. The compound is typically handled under inert conditions to preserve its reactivity.
trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid structure
204378-97-2 structure
Product Name:trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid
CAS No:204378-97-2
MF:C9H11BO2
MW:161.993442773819
MDL:MFCD06798952
CID:2737109
PubChem ID:11062695
Update Time:2025-10-29

trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid Chemical and Physical Properties

Names and Identifiers

    • [(1S,2S)-2-phenylcyclopropyl]boronic acid
    • TRANS-2-PHENYLCYCLOPROPYLBORONIC ACID
    • ((1R,2R)-2-Phenylcyclopropyl)boronic acid
    • [(1beta)-2alpha-Phenylcyclopropyl]boronic acid
    • Rel-((1R,2R)-2-phenylcyclopropyl)boronic acid
    • TRANS-1-PHENYL-CYCLOPROPANE-2-BORONIC ACID
    • trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid
    • MDL: MFCD06798952
    • Inchi: 1S/C9H11BO2/c11-10(12)9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9,11-12H,6H2/t8-,9+/m0/s1
    • InChI Key: JUMGFYYVCWOJDO-DTWKUNHWSA-N
    • SMILES: OB([C@@H]1C[C@H]1C1C=CC=CC=1)O

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 155
  • Topological Polar Surface Area: 40.5

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Additional information on trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid

Introduction to trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid (CAS No. 204378-97-2)

Trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid (CAS No. 204378-97-2) is a versatile boronic acid derivative that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This compound is characterized by its unique cyclic structure, which imparts it with a range of valuable properties and reactivity profiles. In this article, we will delve into the chemical structure, synthesis methods, applications, and recent research advancements associated with this compound.

The chemical structure of trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid is defined by a cyclopropyl ring substituted with a cyclohexyl group and a boronic acid functional group. The cyclopropyl ring is known for its high strain energy, which can be harnessed in various synthetic transformations. The presence of the boronic acid group makes this compound an excellent ligand for transition metal-catalyzed reactions, particularly in cross-coupling reactions such as Suzuki-Miyaura coupling.

One of the key synthetic routes to trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid involves the reaction of a cyclopropyl derivative with a boron reagent. For instance, the hydroboration of a cyclopropyl derivative followed by oxidation can yield the desired boronic acid. This method is widely used due to its efficiency and mild reaction conditions. Recent advancements in catalytic methods have further improved the yield and selectivity of these reactions, making them more accessible for large-scale applications.

In the realm of medicinal chemistry, trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid has shown promise as a building block for the synthesis of bioactive molecules. Its unique structure can be leveraged to create compounds with specific biological activities, such as inhibitors of enzymes or receptors. For example, derivatives of this compound have been explored for their potential as anti-inflammatory agents and anticancer drugs. Recent studies have demonstrated that certain derivatives exhibit selective inhibition of specific protein kinases, which are implicated in various diseases.

The application of trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid extends beyond medicinal chemistry into materials science. The boronic acid group can participate in dynamic covalent chemistry, allowing for the formation of adaptive materials with tunable properties. These materials can be used in various applications, including drug delivery systems, sensors, and self-healing materials. The cyclic structure of the compound also contributes to its stability and mechanical properties, making it suitable for use in advanced materials.

In recent years, there has been a growing interest in the use of boronic acids in polymer chemistry. Trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid can be incorporated into polymer chains to create functional polymers with unique properties. For instance, these polymers can exhibit pH-responsive behavior due to the reversible binding of boronic acids with diols. This property has been exploited in the development of smart hydrogels for controlled drug release and other biomedical applications.

The environmental impact and sustainability of chemical processes are increasingly important considerations in modern research. In this context, the synthesis and use of trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid have been optimized to minimize environmental footprint. Green chemistry principles have been applied to develop more sustainable synthetic routes that reduce waste generation and energy consumption. Additionally, efforts are being made to explore biodegradable derivatives of this compound for applications where environmental compatibility is crucial.

In conclusion, trans-2-Cyclohexyl-cyclopropyl-1-boronic Acid (CAS No. 204378-97-2) is a multifaceted compound with significant potential in various scientific and industrial fields. Its unique chemical structure and reactivity make it an invaluable tool for organic synthesis, medicinal chemistry, materials science, and polymer chemistry. Ongoing research continues to uncover new applications and improve synthetic methods, ensuring that this compound remains at the forefront of chemical innovation.

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