Cas no 76140-13-1 (4-Iodo-6-oxabicyclo3.2.1octan-7-one)

4-Iodo-6-oxabicyclo[3.2.1]octan-7-one is a bicyclic organic compound featuring an iodo substituent and a lactone moiety within its structure. This compound is of interest in synthetic organic chemistry due to its potential as a versatile intermediate for the construction of complex molecular frameworks. The presence of both electrophilic (iodo) and electrophile-reactive (lactone) functional groups allows for selective transformations, including cross-coupling reactions and nucleophilic substitutions. Its rigid bicyclic scaffold may also confer stereochemical control in subsequent synthetic steps. Researchers value this compound for its utility in medicinal chemistry and materials science applications, where precise functionalization of cyclic systems is required.
4-Iodo-6-oxabicyclo3.2.1octan-7-one structure
76140-13-1 structure
Product Name:4-Iodo-6-oxabicyclo3.2.1octan-7-one
CAS No:76140-13-1
MF:C7H9IO2
MW:252.049634695053
CID:2184096
PubChem ID:13487217
Update Time:2025-06-10

4-Iodo-6-oxabicyclo3.2.1octan-7-one Chemical and Physical Properties

Names and Identifiers

    • 4-Iodo-6-oxabicyclo[3.2.1]octan-7-one
    • ALVFLEWPYOOJPZ-UHFFFAOYSA-N
    • 4-iodocyclohexane-1,3-carbolactone
    • MFCD00604194
    • EN300-262332
    • DB-263137
    • (1S, 4S, 5S) -4-iodo-6-oxabicyclo [3.2.1] oct-7-one
    • 76140-13-1
    • CS-0243318
    • SB35136
    • AB86456
    • SY213199
    • SCHEMBL2081774
    • rel-(1R,4R,5R)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one
    • MFCD30802155
    • 4-iodo-6-oxa-bicyclo[3.2.1]octan-7-one
    • (1S,4S,5S)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one
    • SY355152
    • 4-Iodo-6-oxabicyclo3.2.1octan-7-one
    • MDL: MFCD00604194
    • Inchi: 1S/C7H9IO2/c8-5-2-1-4-3-6(5)10-7(4)9/h4-6H,1-3H2
    • InChI Key: ALVFLEWPYOOJPZ-UHFFFAOYSA-N
    • SMILES: IC1CCC2C(=O)OC1C2

Computed Properties

  • Exact Mass: 251.96473g/mol
  • Monoisotopic Mass: 251.96473g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 169
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 3
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.8
  • Topological Polar Surface Area: 26.3?2

4-Iodo-6-oxabicyclo3.2.1octan-7-one Pricemore >>

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Additional information on 4-Iodo-6-oxabicyclo3.2.1octan-7-one

4-Iodo-6-oxabicyclo3.2.1octan-7-one: A Comprehensive Overview

The compound with CAS No 76140-13-1, commonly referred to as 4-Iodo-6-oxabicyclo3.2.1octan-7-one, is a unique bicyclic structure that has garnered significant attention in the fields of organic chemistry and pharmacology. This compound belongs to the class of bicyclic ketones, characterized by its rigid bicyclo[3.2.1]octane skeleton with an oxygen atom at the 6-position and an iodo group at the 4-position. The bicyclo[3.2.1]octane framework is known for its stability and versatility, making it a valuable structure in various chemical applications.

Recent studies have highlighted the potential of 4-Iodo-6-oxabicyclo3.2.1octan-7-one in drug discovery, particularly in the development of bioactive molecules with anti-inflammatory and antioxidant properties. Researchers have explored its ability to act as a scaffold for designing novel therapeutic agents, leveraging its rigid structure to enhance molecular interactions with target proteins.

The synthesis of 4-Iodo-6-oxabicyclo3.2.1octan-7-one involves a multi-step process that typically begins with the preparation of the bicyclic core followed by functionalization at specific positions. One of the most efficient methods reported in the literature involves a Diels-Alder reaction to form the bicyclic system, followed by oxidation to introduce the ketone group at the 7-position and iodination at the 4-position using iodine-based reagents.

One of the most intriguing aspects of this compound is its ability to undergo various transformations while retaining its bicyclic framework. For instance, recent research has demonstrated that 4-Iodo-6-oxabicyclo3.2.1octan-7-one can serve as a versatile building block for constructing more complex molecules with potential medicinal applications. By replacing the iodo group with other functional groups, chemists can tailor the compound's properties for specific biological targets.

In terms of physical properties, 4-Iodo-6-oxabicyclo3.2.1octan-7-one exhibits a melting point of approximately 155°C and is sparingly soluble in common organic solvents such as dichloromethane and ethyl acetate. Its stability under various conditions makes it suitable for use in both laboratory settings and industrial applications.

From an environmental perspective, studies have shown that 4-Iodo-6-oxabicyclo3.2.1octan-7-one has a low toxicity profile, making it a safer alternative to other similar compounds in certain applications. This characteristic aligns with current trends toward green chemistry and sustainable practices in chemical synthesis.

Looking ahead, ongoing research into 4-Iodo-6-oxabicyclo3.2.1octan-7-one is focused on expanding its application in medicinal chemistry, particularly in the design of kinase inhibitors and other enzyme-targeting agents. Its rigid structure provides an ideal platform for optimizing molecular interactions, which is crucial for achieving high potency and selectivity in drug candidates.

In conclusion, 4-Iodo-6 oxabicyclo[3 2 1] octan 7 one (CAS No 76140 13 1) stands out as a promising compound with diverse applications across multiple disciplines within chemistry and pharmacology. Its unique structure, coupled with recent advancements in synthetic methodologies and biological evaluations, positions it as a key player in future innovations within these fields.

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