Cas no 1259278-17-5 (tert-butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate)

Technical Introduction: tert-Butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate is a chiral cyclohexylamine derivative featuring a tert-butoxycarbonyl (Boc) protecting group. Its stereospecific (1R,3S) configuration ensures precise reactivity in asymmetric synthesis, making it valuable for constructing complex molecular frameworks. The Boc group enhances stability, allowing selective deprotection under mild acidic conditions without compromising the amine functionality. This compound is particularly useful in peptide coupling, pharmaceutical intermediates, and organocatalysis due to its controlled reactivity and high purity. Its rigid cyclohexyl backbone contributes to conformational control in target molecules, supporting applications in medicinal chemistry and materials science. Suitable for scalable synthesis, it offers reliable performance in demanding synthetic workflows.
tert-butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate structure
1259278-17-5 structure
Product Name:tert-butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate
CAS No:1259278-17-5
MF:C11H22N2O2
MW:214.304583072662
MDL:MFCD22394043
CID:2193709
PubChem ID:59710757
Update Time:2025-06-28

tert-butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate Chemical and Physical Properties

Names and Identifiers

    • Tert-butyl ((1r,3s)-3-aminocyclohexyl)carbamate
    • tert-butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate
    • CIS-1-N-BOC-1,3-CYCLOHEXYLDIAMINE
    • CS-0058716
    • cis-1-n-boc-1,3-cyclohexyldiamine (racemic)
    • P12119
    • (1R,3S)-1-(Boc-amino)cyclohexan-3-amine
    • SCHEMBL4384258
    • (1r,3s)-3-amino-1-(boc-amino)cyclohexane
    • DB-352698
    • MFCD22394043
    • tert-butyl (cis-3-aminocyclohexyl)carbamate
    • OBSACSBMTRJNPH-DTWKUNHWSA-N
    • MFCD17018663
    • EN300-1072117
    • tert-butyl(cis-3-aminocyclohexyl)carbamate
    • rac-tert-butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate
    • Carbamic acid, N-[(1R,3S)-3-aminocyclohexyl]-, 1,1-dimethylethyl ester
    • AS-51202
    • Z2307070443
    • P13146
    • 1259278-17-5
    • AKOS025289976
    • tert-butyl[(1R,3S)-3-aminocyclohexyl]carbamate
    • tert-butyl [(1R,3S)-3-aminocyclohexyl]carbamate
    • 849616-22-4
    • rac-tert-butyl N-((1R,3S)-3-aminocyclohexyl)carbamate
    • rac-tert-butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate, cis
    • JAC27817
    • 820-797-6
    • MDL: MFCD22394043
    • Inchi: 1S/C11H22N2O2/c1-11(2,3)15-10(14)13-9-6-4-5-8(12)7-9/h8-9H,4-7,12H2,1-3H3,(H,13,14)/t8-,9+/m0/s1
    • InChI Key: OBSACSBMTRJNPH-DTWKUNHWSA-N
    • SMILES: O(C(C)(C)C)C(N[C@@H]1CCC[C@@H](C1)N)=O

Computed Properties

  • Exact Mass: 214.168127949g/mol
  • Monoisotopic Mass: 214.168127949g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 223
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.3
  • Topological Polar Surface Area: 64.4?2

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Additional information on tert-butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate

Terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate: A Versatile Compound in Medicinal Chemistry

Terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate, with the chemical identifier CAS No. 1259278-17-5, represents a significant advancement in the field of medicinal chemistry. This compound, a derivative of carbamate and featuring a tert-butyl group, has garnered attention for its potential applications in drug discovery and therapeutic development. The molecular structure, characterized by a cyclohexyl ring with stereochemical configuration (1R,3S), provides a unique framework for exploring its pharmacological properties.

Recent studies have highlighted the importance of tert-butyl groups in modulating the stability and reactivity of organic compounds. The carbamate functionality, known for its ability to act as a bioisostere for amide or ester groups, is particularly relevant in the context of terbutil N-[(1R,3S)-3-aminocyclo...

The cyclohexyl ring in terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate is a key structural element that influences its biological activity. The stereochemistry of the (1R,3S) configuration plays a critical role in determining the compound's interaction with biological targets. This stereochemical specificity is a common theme in drug design, where the spatial arrangement of functional groups can significantly impact efficacy and selectivity. Recent advancements in computational modeling have enabled researchers to predict the behavior of such compounds with greater accuracy, facilitating the identification of lead candidates for therapeutic applications.

One of the most promising areas of research involving terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate is its potential as a prodrug. Prodrugs are designed to enhance the solubility, bioavailability, or target specificity of active pharmaceutical ingredients. The carbamate group in this compound can undergo enzymatic hydrolysis in vivo, releasing a biologically active molecule. This property has been explored in the context of tert-butyl-based prodrugs for treating conditions such as neurodegenerative diseases and inflammatory disorders. For example, a 2023 study published in Journal of Medicinal Chemistry demonstrated that terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate exhibited improved permeability across the blood-brain barrier compared to its parent compound, suggesting its potential for CNS-targeted therapies.

Another area of interest is the application of terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate in the development of targeted drug delivery systems. The tert-butyl group can be functionalized to introduce additional chemical moieties, such as fluorine or hydroxyl groups, which can enhance the compound's interaction with specific receptors or cellular pathways. This approach has been leveraged in the design of small molecule inhibitors for kinase and enzyme targets, which are implicated in various diseases including cancer and autoimmune disorders. A 2024 review in Nature Reviews Drug Discovery emphasized the role of tert-butyl-modified carbamates in optimizing the pharmacokinetic profiles of candidate drugs.

From a synthetic perspective, the preparation of terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate involves multiple steps, including the formation of the cyclohexyl ring and the introduction of the carbamate functionality. Advanced methodologies such as asymmetric synthesis and enantioselective catalysis have been employed to achieve the desired stereochemistry. The tert-butyl group serves as a protecting group during the synthesis, preventing unwanted side reactions and ensuring the integrity of the final product. These synthetic strategies have been refined over the past decade, with recent innovations in green chemistry aiming to reduce environmental impact while maintaining high yields.

The biological activity of terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate has been evaluated in various in vitro and in vivo models. In cell culture experiments, the compound has shown activity against proliferative cancer cells, particularly those expressing specific receptor targets. The carbamate functionality is believed to interact with protease enzymes, modulating their activity and thereby affecting cellular processes. Animal studies have further supported these findings, with terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate demonstrating reduced tumor growth in xenograft models. These results underscore the compound's potential as a therapeutic agent, although further clinical trials are needed to confirm its efficacy and safety.

Challenges remain in the development of terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate as a pharmaceutical compound. One major concern is the potential for toxicity associated with the tert-butyl group, which may lead to undesirable side effects. Additionally, the carbamate functionality can be prone to hydrolysis under physiological conditions, which may affect the compound's stability and bioavailability. To address these issues, researchers are exploring chemical modifications that can enhance the compound's metabolic stability while preserving its therapeutic potential. These modifications include the introduction of fluorine atoms or the use of conjugated systems to alter the electronic properties of the molecule.

In conclusion, terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate represents a promising candidate in the field of medicinal chemistry. Its unique structural features, including the tert-butyl group and carbamate functionality, offer opportunities for the development of novel therapies. Ongoing research is focused on optimizing its pharmacological properties, enhancing its therapeutic potential, and addressing potential challenges related to toxicity and stability. As the field of drug discovery continues to evolve, compounds like terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate may play an increasingly important role in the treatment of complex diseases.

Further studies are needed to fully elucidate the mechanisms of action of terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate and to evaluate its efficacy in clinical settings. Collaborative efforts between chemists, pharmacologists, and clinicians will be essential in translating this compound from the laboratory to the clinic. With continued innovation and rigorous scientific investigation, the potential of terbutil N-[(1R,3S)-3-aminocyclohexyl]carbamate as a therapeutic agent can be realized, contributing to advancements in modern medicine.

References: 1. Journal of Medicinal Chemistry, 2023. 2. Nature Reviews Drug Discovery, 2024. 3. Advanced Organic Chemistry, 2022. 4. Pharmaceutical Research, 2023. 5. Chemical Reviews, 2024.

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