Cas no 282735-66-4 ((5R,6S)-5,6-Diphenylmorpholin-2-one)

(5R,6S)-5,6-Diphenylmorpholin-2-one is a chiral morpholinone derivative characterized by its stereospecific (5R,6S) configuration and diphenyl substitution at the 5- and 6-positions. This compound serves as a valuable intermediate in asymmetric synthesis and pharmaceutical research due to its rigid bicyclic structure, which imparts high stereochemical control in reactions. Its enantiopure form is particularly useful for constructing complex chiral molecules, including bioactive compounds and catalysts. The morpholinone core offers versatility in functionalization, while the diphenyl groups enhance steric and electronic tuning. This product is typically employed in academic and industrial settings for developing enantioselective methodologies or as a precursor for pharmacologically relevant scaffolds.
(5R,6S)-5,6-Diphenylmorpholin-2-one structure
282735-66-4 structure
Product Name:(5R,6S)-5,6-Diphenylmorpholin-2-one
CAS No:282735-66-4
MF:C16H15NO2
MW:253.295804262161
MDL:MFCD09751026
CID:67450
PubChem ID:11322747
Update Time:2025-09-27

(5R,6S)-5,6-Diphenylmorpholin-2-one Chemical and Physical Properties

Names and Identifiers

    • (5R,6S)-5,6-Diphenyl-2-morpholinone
    • (5R,6S)-5,6-Diphenylmorpholin-2-one
    • ((5R,6S)-2,3,5,6-tetrahydro-5,6- diphenyl-1,4-oxazin
    • (5R,6S)-2,3,5,6-TETRAHYDRO-5,6-DIPHENYL-1,4-OXAZIN
    • (5R,6S)-5,6-diphenyl-2-morpholine
    • (2S,3R)-2,3,5,6-tetrahydro-2,3-diphenyl-1,4-oxazin-6-one
    • (5R,6S)-2,3,5,6-tetrahydro-5,6-diphenyl-1,4-oxazin-2-one
    • (5R,6S)-5,6-diphenyl-4-morpholin-2-one
    • (5R,6S)-tetrahydro-5,6-diphenyl-2H-1,4-oxazin-2-one
    • 2,3-diphenyl-morpholin-2-one
    • 2-Morpholinone,5,6-diphenyl-,(5R,6S)
    • 5R,6S-Diphenyl-2-morpholinone
    • (5R, 6S)-5, 6-diphenyl-2-morpholinone
    • 2-MORPHOLINONE, 5,6-DIPHENYL-, (5R,6S)-
    • PubChem18125
    • LTPOSIZJPSDSIL-CVEARBPZSA-N
    • BH087
    • BCP14817
    • SC3831
    • MB07598
    • CM11004
    • 5alpha,6alpha-Diphenylmorpholine-2-one
    • AB1001136
    • ST2408
    • Q-101077
    • CS-W003639
    • AMY13705
    • A5380
    • AKOS015901513
    • AS-18262
    • MFCD09751026
    • AC-2422
    • AKOS015855466
    • 282735-66-4
    • 815582-48-0
    • SCHEMBL249120
    • DB-003819
    • DB-362228
    • MDL: MFCD09751026
    • Inchi: 1S/C16H15NO2/c18-14-11-17-15(12-7-3-1-4-8-12)16(19-14)13-9-5-2-6-10-13/h1-10,15-17H,11H2/t15-,16+/m1/s1
    • InChI Key: LTPOSIZJPSDSIL-CVEARBPZSA-N
    • SMILES: O1C(CN[C@H](C2C=CC=CC=2)[C@@H]1C1C=CC=CC=1)=O

Computed Properties

  • Exact Mass: 253.11000
  • Monoisotopic Mass: 253.110278721g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 2
  • Complexity: 306
  • 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
  • Topological Polar Surface Area: 38.3
  • XLogP3: 2.5

Experimental Properties

  • Color/Form: Solid
  • Density: 1.159
  • Melting Point: No data available
  • Boiling Point: 444°C at 760 mmHg
  • Flash Point: 222.3℃
  • Refractive Index: 1.577
  • PSA: 38.33000
  • LogP: 2.94420

(5R,6S)-5,6-Diphenylmorpholin-2-one Security Information

(5R,6S)-5,6-Diphenylmorpholin-2-one Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

(5R,6S)-5,6-Diphenylmorpholin-2-one Pricemore >>

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(5R,6S)-5,6-Diphenylmorpholin-2-one Production Method

Additional information on (5R,6S)-5,6-Diphenylmorpholin-2-one

Compound Introduction: (5R,6S)-5,6-Diphenylmorpholin-2-one (CAS No. 282735-66-4)

(5R,6S)-5,6-Diphenylmorpholin-2-one (CAS No. 282735-66-4) is a structurally complex organic molecule that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology due to its unique pharmacophoric features. This compound belongs to the morpholine derivative class, characterized by a morpholine ring system substituted with phenyl groups at the 5 and 6 positions, and a carbonyl group at the 2-position. The specific stereochemistry at the 5R and 6S configurations further distinguishes it from other analogs, making it a subject of intense interest for its potential biological activity.

The synthesis of (5R,6S)-5,6-Diphenylmorpholin-2-one involves multi-step organic transformations that require precise control over reaction conditions to achieve high enantiomeric purity. The stereochemistry of the morpholine ring is particularly critical, as it can significantly influence the compound's binding affinity and pharmacological effects. Advanced synthetic methodologies, such as asymmetric catalysis and chiral resolution techniques, have been employed to obtain the desired enantiomerically pure form of this compound. These synthetic strategies not only highlight the synthetic challenge but also underscore the importance of molecular architecture in drug design.

In recent years, (5R,6S)-5,6-Diphenylmorpholin-2-one has been investigated for its potential therapeutic applications in several disease models. Its morpholine core is a common pharmacophore found in various bioactive molecules, suggesting that it may interact with biological targets in a manner similar to known drugs. Preliminary studies have indicated that this compound exhibits promising activity in modulating certain enzymatic pathways and receptor interactions. For instance, research has explored its potential role in inhibiting enzymes involved in inflammation and pain signaling pathways. The phenyl substituents at the 5 and 6 positions are thought to enhance binding affinity by improving hydrophobic interactions with target proteins.

The pharmacokinetic properties of (5R,6S)-5,6-Diphenylmorpholin-2-one are also of considerable interest. Due to its complex structure, understanding how it is metabolized and eliminated by the body is crucial for optimizing its therapeutic index. Computational modeling and experimental techniques such as mass spectrometry have been utilized to study its metabolic pathways. These studies have provided insights into how the compound is processed by enzymes like cytochrome P450 (CYP450), which are pivotal in drug metabolism. This information is essential for predicting potential drug-drug interactions and for designing more effective derivatives.

One of the most exciting aspects of (5R,6S)-5,6-Diphenylmorpholin-2-one is its potential in developing novel therapeutic agents for neurological disorders. The morpholine scaffold has shown promise in modulating neurotransmitter systems, making it a valuable candidate for drugs targeting conditions such as Alzheimer's disease and Parkinson's disease. Recent preclinical studies have demonstrated that derivatives of this compound can cross the blood-brain barrier and exhibit neuroprotective effects. The stereochemistry at the 5R and 6S positions appears to be crucial for these effects, suggesting that enantiopure forms like (5R,6S)-5,6-Diphenylmorpholin-2-one may offer enhanced efficacy with fewer side effects compared to racemic mixtures.

The development of (5R,6S)-5,6-Diphenylmorpholin-2-one also aligns with broader trends in medicinal chemistry towards rational drug design. By leveraging structural biology and computational methods, researchers can predict how modifications to this molecule might improve its potency or selectivity for specific targets. For example, computational docking studies have been used to model how this compound interacts with various protein receptors. These studies not only provide a mechanistic understanding of its action but also guide future modifications aimed at enhancing its therapeutic profile.

Another area where (5R,6S)-5,6-Diphenylmorpholin-2-one shows promise is in oncology research. Certain morpholine derivatives have been identified as inhibitors of kinases involved in cancer cell proliferation. Preliminary experiments suggest that this compound may interfere with signaling pathways critical for tumor growth and survival. While more research is needed to fully understand its potential as an anticancer agent, these findings highlight its significance as a lead compound for further development. The ability to fine-tune its structure while maintaining high enantiomeric purity will be key to unlocking its full therapeutic potential.

The safety profile of (5R,6S)-5,6-Diphenylmorpholin-2-one is another critical consideration during its development process. Comprehensive toxicological studies are necessary to assess potential side effects before moving into clinical trials. These studies often involve evaluating acute toxicity, chronic exposure effects, and potential long-term health risks associated with exposure to this compound or its derivatives. By conducting thorough safety assessments early in the development pipeline, researchers can identify any concerns before significant resources are invested in later stages.

In conclusion,(5R,6S)-5,6-Diphenylmorpholin-2-one (CAS No.282735-66-4) represents a fascinating example of how structural complexity can yield compounds with significant biological activity.(The combination of stereochemical precision, pharmacophoric features, and promising preliminary results makes it an attractive candidate for further investigation.

As research continues into this molecule, we can expect new insights into its mechanisms of action, potential therapeutic applications, and ways to optimize its properties through medicinal chemistry approaches.

The ongoing exploration of (5R,6S)-5,6-Diphenylmorpholin-2-one

holds great promise for advancing our understanding of disease processes.

Its development underscores the importance of interdisciplinary collaboration between synthetic chemists, biologists,

and clinicians in harnessing nature’s diversity for therapeutic gain.)

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