Cas no 161564-10-9 ((3R,5R)-1-benzylpiperidine-3,5-diol)

(3R,5R)-1-Benzylpiperidine-3,5-diol is a chiral piperidine derivative characterized by its stereospecific hydroxyl groups at the 3 and 5 positions, along with a benzyl substituent at the nitrogen atom. This compound is of interest in synthetic organic chemistry and pharmaceutical research due to its rigid, functionalized structure, which serves as a versatile intermediate for the development of bioactive molecules. The (3R,5R) configuration ensures high enantiomeric purity, making it valuable for asymmetric synthesis and chiral ligand design. Its diol functionality allows for further derivatization, enhancing its utility in medicinal chemistry applications, such as enzyme inhibition or receptor modulation. The compound’s stability and well-defined stereochemistry contribute to its reproducibility in research settings.
(3R,5R)-1-benzylpiperidine-3,5-diol structure
161564-10-9 structure
Product Name:(3R,5R)-1-benzylpiperidine-3,5-diol
CAS No:161564-10-9
MF:C12H17NO2
MW:207.268883466721
MDL:MFCD10697908
CID:1341129
PubChem ID:11830614
Update Time:2025-06-07

(3R,5R)-1-benzylpiperidine-3,5-diol Chemical and Physical Properties

Names and Identifiers

    • 3,5-Piperidinediol, 1-(phenylmethyl)-, (3R,5R)-
    • (3R,5R)-1-benzylpiperidine-3,5-diol
    • (3R,5R)-1-Benzyl-piperidine-3,5-diol
    • 913832-01-6
    • 161564-10-9
    • AT24410
    • EN300-19725141
    • trans-1-Benzyl-piperidine-3,5-diol
    • Rel-(3R,5R)-1-benzylpiperidine-3,5-diol
    • SCHEMBL1873859
    • MDL: MFCD10697908
    • Inchi: 1S/C12H17NO2/c14-11-6-12(15)9-13(8-11)7-10-4-2-1-3-5-10/h1-5,11-12,14-15H,6-9H2/t11-,12-/m1/s1
    • InChI Key: ARTDOWDQPXVXAF-VXGBXAGGSA-N
    • SMILES: O[C@H]1CN(CC2C=CC=CC=2)C[C@@H](C1)O

Computed Properties

  • Exact Mass: 207.12601
  • Monoisotopic Mass: 207.125928785g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 182
  • 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: 0.7
  • Topological Polar Surface Area: 43.7?2

Experimental Properties

  • PSA: 43.7

(3R,5R)-1-benzylpiperidine-3,5-diol Pricemore >>

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(3R,5R)-1-benzylpiperidine-3,5-diol Related Literature

Additional information on (3R,5R)-1-benzylpiperidine-3,5-diol

Introduction to (3R,5R)-1-Benzylpiperidine-3,5-diol (CAS No. 161564-10-9)

(3R,5R)-1-Benzylpiperidine-3,5-diol (CAS No. 161564-10-9) is a chiral compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research due to its unique structural features and potential biological activities. This compound belongs to the class of piperidines, which are nitrogen-containing heterocyclic compounds with a wide range of applications in drug discovery and development.

The (3R,5R)-1-Benzylpiperidine-3,5-diol molecule is characterized by its benzyl substituent and two hydroxyl groups at the 3 and 5 positions of the piperidine ring. The presence of these functional groups imparts specific chemical and biological properties that make it a valuable candidate for various therapeutic applications. Recent studies have highlighted its potential as a lead compound in the development of novel drugs for neurological disorders, cancer, and other diseases.

In terms of its chemical structure, (3R,5R)-1-Benzylpiperidine-3,5-diol is a chiral molecule with two stereocenters at the 3 and 5 positions. The absolute configuration at these centers is crucial for its biological activity, as small changes in stereochemistry can significantly affect the compound's interactions with biological targets. This chiral nature has led to extensive research on the synthesis and resolution of enantiomers to optimize its therapeutic potential.

One of the key areas of research involving (3R,5R)-1-Benzylpiperidine-3,5-diol is its role as a modulator of ion channels and receptors. Studies have shown that this compound can interact with various ion channels, such as potassium and sodium channels, which are involved in the regulation of neuronal excitability. This property makes it a promising candidate for the treatment of neurological disorders such as epilepsy and neuropathic pain.

Additionally, (3R,5R)-1-Benzylpiperidine-3,5-diol has been investigated for its potential anticancer properties. Research has demonstrated that it can inhibit the growth of cancer cells by interfering with signaling pathways involved in cell proliferation and survival. Specifically, it has been shown to induce apoptosis in cancer cells through the modulation of key proteins such as Bcl-2 and p53. These findings suggest that (3R,5R)-1-Benzylpiperidine-3,5-diol could be developed into a novel anticancer agent with fewer side effects compared to traditional chemotherapy drugs.

The synthesis of (3R,5R)-1-Benzylpiperidine-3,5-diol has been a focus of numerous studies due to its importance in pharmaceutical research. Various synthetic routes have been developed to produce this compound with high enantiomeric purity. One common approach involves the use of chiral catalysts or chiral auxiliaries to control the stereochemistry during the synthesis process. These methods have enabled researchers to produce gram quantities of (3R,5R)-1-Benzylpiperidine-3,5-diol for further biological evaluation.

In addition to its therapeutic potential, (3R,5R)-1-Benzylpiperidine-3,5-diol has also been studied for its use as a building block in the synthesis of more complex molecules. Its versatile functional groups make it an attractive starting material for the preparation of derivatives with enhanced biological activities or improved pharmacokinetic properties. For example, researchers have explored the modification of the benzyl group or the introduction of additional functional groups to enhance the compound's selectivity and potency.

The pharmacological profile of (3R,5R)-1-Benzylpiperidine-3,5-diol has been extensively evaluated in preclinical studies using both in vitro and in vivo models. These studies have provided valuable insights into its mechanism of action and safety profile. In vitro assays have demonstrated that (3R,5R)-1-Benzylpiperidine-3,5-diol exhibits potent activity against various cell lines derived from different types of cancer. In vivo studies using animal models have further confirmed its efficacy in reducing tumor growth and improving survival rates.

Despite its promising therapeutic potential, there are still several challenges associated with the development of (3R,5R)-1-Benzylpiperidine-3,5-diol as a drug candidate. One major challenge is optimizing its pharmacokinetic properties to ensure adequate bioavailability and distribution to target tissues. Researchers are actively working on developing prodrugs or formulations that can enhance the compound's stability and solubility while minimizing toxicity.

Another area of ongoing research is understanding the long-term safety and efficacy of (3R,5R)-1-Benzylpiperidine-3,5-diol in humans. Preclinical studies have shown promising results, but more extensive clinical trials are needed to validate these findings and assess any potential side effects or adverse reactions. Ongoing clinical trials are currently evaluating (3R,5R)-1-Benzylpiperidine-3,5-diol for various indications, including neurological disorders and cancer.

In conclusion, (3R,5R)-1-Benzylpiperidine-3,5-diol (CAS No. 161564-10-9) is a promising compound with significant potential in pharmaceutical research and development. Its unique chemical structure and biological activities make it an attractive candidate for further investigation as a lead compound in drug discovery programs. As research continues to advance our understanding of this molecule's properties and mechanisms of action, it is likely that new applications will emerge, contributing to the development of innovative therapies for various diseases.

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