Cas no 153546-27-1 ((2R)-2-cyclohexyloxirane)

(2R)-2-Cyclohexyloxirane is a chiral epoxide compound characterized by a cyclohexyl group attached to the oxirane ring at the 2-position with (R)-configuration. This stereospecific structure makes it a valuable intermediate in asymmetric synthesis, particularly for the production of enantiomerically pure pharmaceuticals and fine chemicals. Its high reactivity toward nucleophilic ring-opening reactions enables selective functionalization, facilitating the construction of complex chiral molecules. The cyclohexyl moiety enhances lipophilicity, which can be advantageous in drug design for improved membrane permeability. As an optically active building block, it offers precise control over stereochemistry in synthetic routes. The compound's stability under standard conditions allows for convenient handling and storage in synthetic applications.
(2R)-2-cyclohexyloxirane structure
(2R)-2-cyclohexyloxirane structure
Product Name:(2R)-2-cyclohexyloxirane
CAS No:153546-27-1
MF:C8H14O
MW:126.196162700653
CID:1333358
PubChem ID:11355483
Update Time:2025-06-19

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

Names and Identifiers

    • (2R)-2-cyclohexyloxirane
    • oxirane, 2-cyclohexyl-, (2R)-
    • LogP
    • EN300-1833250
    • SCHEMBL21257908
    • 153546-27-1
    • Inchi: 1S/C8H14O/c1-2-4-7(5-3-1)8-6-9-8/h7-8H,1-6H2/t8-/m0/s1
    • InChI Key: NPRYHWFMGPYJIY-QMMMGPOBSA-N
    • SMILES: O1C[C@H]1C1CCCCC1

Computed Properties

  • Exact Mass: 126.10452
  • Monoisotopic Mass: 126.104465066g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 94.7
  • 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: 2.3
  • Topological Polar Surface Area: 12.5?2

Experimental Properties

  • PSA: 12.53

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Additional information on (2R)-2-cyclohexyloxirane

Introduction to (2R)-2-cyclohexyloxirane and Its Significance in Modern Chemical Biology

Chemical entities often hold the key to unlocking novel therapeutic strategies in the field of pharmaceuticals and biotechnology. Among these, (2R)-2-cyclohexyloxirane (CAS No. 153546-27-1) stands out as a compound of considerable interest due to its unique structural properties and potential applications. This enantiomerically pure oxirane derivative has garnered attention for its role in synthetic chemistry, particularly in the development of chiral catalysts and intermediates for complex molecular architectures.

The CAS number 153546-27-1 provides a unique identifier for this compound, ensuring precise classification and reference within scientific literature. The structural motif of (2R)-2-cyclohexyloxirane, featuring a cyclohexyl group attached to an epoxide ring, offers a versatile platform for further functionalization. This characteristic makes it an invaluable building block in the synthesis of pharmacologically active molecules, where stereochemistry plays a pivotal role in determining biological activity.

In recent years, advancements in chemical biology have highlighted the importance of enantiopure compounds in drug discovery. The enantiomeric purity of (2R)-2-cyclohexyloxirane is particularly noteworthy, as it allows for the development of highly selective synthetic routes. Such selectivity is crucial in minimizing side reactions and improving overall yield, which are critical factors in industrial-scale pharmaceutical production.

The reactivity of the epoxide ring in (2R)-2-cyclohexyloxirane has been extensively studied for its potential in forming carbon-carbon bonds through ring-opening reactions. This property has been exploited in various synthetic protocols, including the preparation of complex natural products and novel drug candidates. For instance, recent studies have demonstrated its utility in constructing heterocyclic frameworks, which are prevalent in many bioactive compounds.

One notable application of (2R)-2-cyclohexyloxirane lies in its use as a chiral auxiliary in asymmetric synthesis. Chiral auxiliaries are essential tools in organic chemistry that facilitate the formation of enantiomerically enriched products. The cyclohexyl group in this compound provides steric hindrance and electronic effects that influence the outcome of catalytic reactions, making it an effective tool for achieving high enantioselectivity.

Recent research has also explored the role of (2R)-2-cyclohexyloxirane in medicinal chemistry. Its structural features have been leveraged to develop novel inhibitors targeting specific biological pathways. For example, derivatives of this compound have shown promise as inhibitors of enzymes involved in cancer metabolism. These findings underscore the compound's potential as a scaffold for drug development, particularly in oncology research.

The synthesis of (2R)-2-cyclohexyloxirane itself is a testament to the progress made in synthetic methodologies over recent decades. Modern techniques such as transition-metal catalysis and biocatalysis have enabled more efficient and sustainable routes to complex molecules like this one. These advancements not only improve yield but also reduce waste, aligning with the growing emphasis on green chemistry principles.

In conclusion, (2R)-2-cyclohexyloxirane (CAS No. 153546-27-1) represents a significant advancement in chemical biology and pharmaceutical research. Its unique structural features and reactivity make it a valuable tool for synthetic chemists and medicinal chemists alike. As research continues to uncover new applications for this compound, its importance is likely to grow further, contributing to the development of innovative therapeutic strategies.

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