Cas no 1313176-45-2 ((2R)-2-ethylmorpholine)

(2R)-2-ethylmorpholine is a chiral morpholine derivative characterized by its stereospecific (R)-configuration at the 2-position and an ethyl substituent. This compound is primarily utilized as a versatile intermediate in asymmetric synthesis, particularly in pharmaceutical and agrochemical applications where enantioselectivity is critical. Its rigid morpholine ring structure enhances stability, while the ethyl group provides moderate lipophilicity, influencing solubility and reactivity. The (R)-enantiomer is often preferred for its selective interactions in chiral catalysis and resolution processes. High purity grades ensure reproducibility in complex syntheses, making it valuable for research and industrial-scale production. Proper handling is advised due to potential reactivity with strong acids or oxidizing agents.
(2R)-2-ethylmorpholine structure
(2R)-2-ethylmorpholine structure
Product Name:(2R)-2-ethylmorpholine
CAS No:1313176-45-2
MF:C6H13NO
MW:115.173521757126
MDL:MFCD14635494
CID:1023873
PubChem ID:25497577
Update Time:2025-05-24

(2R)-2-ethylmorpholine Chemical and Physical Properties

Names and Identifiers

    • (R)-2-Ethylmorpholine
    • (2R)-2-ethylmorpholine
    • (R)-2-Ethyl-morpholine
    • DB-336226
    • (S)-2-ETHYLMORPHOLINE HCL
    • AMY21361
    • Morpholine,2-ethyl-,(2R)-
    • D75750
    • Morpholine, 2-ethyl-, (2R)-
    • A856557
    • AKOS016843329
    • DTXSID10649702
    • RGNFMQJLAOONTP-ZCFIWIBFSA-N
    • 1313176-45-2
    • SCHEMBL12524834
    • EN300-2966853
    • CS-0096526
    • MDL: MFCD14635494
    • Inchi: 1S/C6H13NO/c1-2-6-5-7-3-4-8-6/h6-7H,2-5H2,1H3/t6-/m1/s1
    • InChI Key: RGNFMQJLAOONTP-ZCFIWIBFSA-N
    • SMILES: O1CCNC[C@H]1CC

Computed Properties

  • Exact Mass: 115.099714038g/mol
  • Monoisotopic Mass: 115.099714038g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 1
  • Complexity: 65.5
  • 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: 0.4
  • Topological Polar Surface Area: 21.3?2

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Additional information on (2R)-2-ethylmorpholine

Introduction to (2R)-2-Ethylmorpholine (CAS No. 1313176-45-2)

Morpholine derivatives have long been of interest in the fields of organic chemistry and pharmacology due to their unique structural properties and versatile applications. Among these, (2R)-2-ethylmorpholine, with its CAS registry number 1313176-45-2, stands out as a compound with significant potential in various chemical and biological contexts. This article delves into the structural characteristics, synthesis methods, and recent advancements in the application of (2R)-2-ethylmorpholine, providing a comprehensive overview of its role in contemporary research.

The morpholine ring system is a six-membered heterocycle containing one oxygen atom and one nitrogen atom. In the case of (2R)-2-ethylmorpholine, the ethyl group is attached to the second carbon of the morpholine ring, imparting specific steric and electronic properties to the molecule. This configuration not only influences the compound's physical properties but also plays a crucial role in its reactivity and biological activity. Recent studies have highlighted the importance of stereochemistry in morpholine derivatives, with (2R)-configuration being particularly advantageous in certain catalytic applications.

Synthesis of (2R)-2-ethylmorpholine has been extensively explored, with researchers employing various methodologies to achieve high yields and enantioselectivity. One prominent approach involves the use of chiral catalysts in asymmetric synthesis, enabling the controlled formation of the (2R) enantiomer. This method has been optimized in recent years, with advancements in catalytic systems significantly improving both reaction efficiency and product purity. The ability to synthesize (2R)-2-ethylmorpholine with high enantiomeric excess has opened new avenues for its application in asymmetric catalysis and drug discovery.

In terms of applications, (2R)-2-ethylmorpholine has demonstrated remarkable potential as a chiral ligand in organocatalysis. Its ability to induce asymmetry in various organic transformations has made it a valuable tool in the synthesis of complex molecules, including pharmaceutical agents. Recent research has focused on its role as a catalyst in aldol reactions and Michael additions, where it has shown exceptional efficiency compared to traditional ligands. The compound's versatility is further underscored by its use as a building block in medicinal chemistry, where it contributes to the design of bioactive compounds with improved pharmacokinetic profiles.

The structural uniqueness of (2R)-2-ethylmorpholine also lends itself well to polymer chemistry. Researchers have investigated its use as a monomer in the synthesis of novel polymers with tailored properties, such as enhanced thermal stability and mechanical strength. These polymers have potential applications in advanced materials science, including high-performance composites and biodegradable plastics. The integration of (2R)-configuration into polymer frameworks has been shown to significantly influence material properties, highlighting the compound's multifaceted utility.

Recent advancements in computational chemistry have further elucidated the electronic structure and reactivity of (2R)-2-ethylmorpholine. Quantum mechanical studies have provided insights into its π-electron distribution and hydrogen bonding capabilities, which are critical factors in determining its interaction with other molecules. These findings have been instrumental in guiding experimental designs for new applications, such as its use as a stabilizing agent in reactive intermediates or as a component in green chemistry processes.

In conclusion, (2R)-2-ethylmorpholine (CAS No. 1313176-45-2) is a compound that continues to captivate researchers across multiple disciplines due to its unique properties and diverse applications. From asymmetric catalysis to polymer science, this morpholine derivative exemplifies the potential of chiral compounds in advancing modern chemistry. As research progresses, it is anticipated that (2R)-configuration-specific studies will unlock even more innovative uses for this intriguing molecule.

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