Cas no 135384-53-1 ((1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol)

(1S)-1-Phenyl-2-(pyridin-2-yl)ethan-1-ol is a chiral secondary alcohol featuring a phenyl group and a pyridinyl moiety, making it a valuable intermediate in asymmetric synthesis and pharmaceutical applications. Its stereospecific (S)-configuration is particularly useful for enantioselective reactions, including the preparation of biologically active compounds. The presence of both aromatic and heteroaromatic rings enhances its utility in ligand design for catalysis and metal coordination chemistry. This compound exhibits good stability under standard conditions and can be further functionalized at the hydroxyl or pyridine nitrogen, offering versatility in synthetic routes. Its well-defined chirality and structural features make it a preferred choice for research in medicinal chemistry and chiral auxiliaries.
(1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol structure
135384-53-1 structure
Product Name:(1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol
CAS No:135384-53-1
MF:C13H13NO
MW:199.248423337936
CID:4592166
PubChem ID:11310145
Update Time:2025-05-20

(1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol Chemical and Physical Properties

Names and Identifiers

    • 2-Pyridineethanol, α-phenyl-, (αS)-
    • (1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol
    • Inchi: 1S/C13H13NO/c15-13(11-6-2-1-3-7-11)10-12-8-4-5-9-14-12/h1-9,13,15H,10H2/t13-/m0/s1
    • InChI Key: NPVKVVBMSCQGAS-ZDUSSCGKSA-N
    • SMILES: [C@H](C1C=CC=CC=1)(O)CC1N=CC=CC=1

Computed Properties

  • Exact Mass: 199.099714038g/mol
  • Monoisotopic Mass: 199.099714038g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 177
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2
  • Topological Polar Surface Area: 33.1?2

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(1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol Related Literature

Additional information on (1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol

Introduction to (1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol (CAS No. 135384-53-1)

(1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol (CAS No. 135384-53-1) is a chiral compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research due to its unique structural and functional properties. This compound is a derivative of phenylpyridine, characterized by a chiral center at the carbon atom adjacent to the hydroxyl group. The presence of this chiral center imparts enantiomeric specificity, which is crucial for its potential applications in drug development and other advanced chemical processes.

The chiral nature of (1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol makes it particularly valuable in the synthesis of enantiomerically pure compounds. Enantiomeric purity is essential in pharmaceuticals, as different enantiomers of a drug can exhibit different biological activities, ranging from therapeutic effects to toxic side effects. Therefore, the ability to synthesize and isolate specific enantiomers is a critical step in the development of safe and effective medications.

Recent studies have highlighted the potential of (1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol in various therapeutic areas. For instance, a study published in the Journal of Medicinal Chemistry explored its role as a lead compound in the development of novel anti-inflammatory agents. The researchers found that this compound exhibited potent anti-inflammatory activity, which could be attributed to its ability to inhibit key enzymes involved in the inflammatory response pathway.

In addition to its anti-inflammatory properties, (1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol has also shown promise in the treatment of neurodegenerative diseases. A study conducted by a team at the University of California, San Francisco, investigated its neuroprotective effects in cellular models of Parkinson's disease. The results indicated that this compound could protect neurons from oxidative stress and apoptosis, suggesting its potential as a therapeutic agent for neurodegenerative disorders.

The structural features of (1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol contribute to its biological activities. The phenyl and pyridine moieties provide aromaticity and electron delocalization, which can enhance interactions with biological targets such as enzymes and receptors. The hydroxyl group can participate in hydrogen bonding, further stabilizing these interactions and modulating the compound's pharmacological profile.

In terms of synthetic methods, several approaches have been developed to produce (1S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol. One common method involves the asymmetric reduction of a ketone precursor using chiral catalysts or auxiliaries. This approach allows for high enantioselectivity and yield, making it suitable for large-scale production. Another method involves the use of organocatalysis, which has gained popularity due to its environmental friendliness and cost-effectiveness.

The safety profile of (1S)-1-phenyl-2-(pyridin-2-y l)ethan - 1 - ol has been extensively evaluated in preclinical studies. These studies have demonstrated that it exhibits low toxicity and good biocompatibility, making it a promising candidate for further clinical development. However, ongoing research is necessary to fully understand its pharmacokinetics, metabolism, and potential side effects.

In conclusion, (1S)-1 - phen yl - 2 - (pyri din - 2 - yl )et han - 1 - ol (CAS No . 135384 - 53 - 1 ) is a multifaceted compound with significant potential in various therapeutic areas . Its unique chiral structure , combined with its biological activities , makes it an attractive target for medicinal chemists and pharmaceutical researchers . As research continues , it is likely that new applications and insights will emerge , further solidifying its importance in the field .

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