Cas no 29179-13-3 (6-phenylhexa-3,5-dien-2-one)

6-Phenylhexa-3,5-dien-2-one is an α,β-unsaturated ketone featuring a conjugated diene system and a phenyl substituent, making it a versatile intermediate in organic synthesis. Its extended π-electron system enhances reactivity in cycloaddition and Michael addition reactions, facilitating the construction of complex cyclic structures. The compound's structural features also lend utility in photochemical studies and as a precursor for pharmaceuticals and agrochemicals. Its well-defined conjugation allows for predictable regioselectivity in electrophilic and nucleophilic transformations. The product is typically characterized by high purity, ensuring consistent performance in research and industrial applications. Proper handling under inert conditions is recommended due to potential sensitivity to light and air.
6-phenylhexa-3,5-dien-2-one structure
6-phenylhexa-3,5-dien-2-one structure
Product Name:6-phenylhexa-3,5-dien-2-one
CAS No:29179-13-3
MF:C12H12O
MW:172.223083496094
CID:291152
PubChem ID:5708783
Update Time:2025-06-08

6-phenylhexa-3,5-dien-2-one Chemical and Physical Properties

Names and Identifiers

    • 3,5-Hexadien-2-one,6-phenyl-, (3E,5E)-
    • (3E,5Z)-6-phenylhexa-3,5-dien-2-one
    • (1-Cinnamoyl-5-methoxy-2-methyl-3-indolyl)-essigsaeure
    • [5-methoxy-2-methyl-1-(3-phenyl-acryloyl)-indol-3-yl]-acetic acid
    • 1-(1-Oxo-3-phenyl-2-propenyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid
    • 1-cinnamoyl-5-methoxy-2-methyl-1-indole-3-acetic acid
    • 1-Cinnamoyl-5-methoxy-2-methyl-indol-
    • 5-Methoxy-2-methyl-1-(1-oxo-3-phenyl-2-propenyl)-1H-indole-3-acetic acid
    • Cindomet
    • cinmetacine
    • cinmethacin
    • cinnamalacetone
    • Indolacin
    • 6-phenylhexa-3,5-dien-2-one
    • 4173-44-8
    • (3E,5E)-6-phenylhexa-3,5-dien-2-one
    • SCHEMBL10911551
    • Cinnamylidenaceton
    • (3E,5E)-6-Phenyl-hexa-3,5-dien-2-one
    • CS-0274602
    • EINECS 224-036-3
    • SCHEMBL141554
    • CHEBI:173791
    • 29179-13-3
    • 3,5-Hexadien-2-one, 6-phenyl-
    • (3E,5E)-6-phenyl-3,5-hexadien-2-one
    • 6-phenyl-hexa-3,5-dien-2-one
    • 6-phenyl-3,5-hexadien-2-one
    • PRNUCJKOERXADE-YLNKAEQOSA-N
    • AKOS009159315
    • CHEMBL104778
    • Cinnamylideneacetone
    • EN300-1861463
    • Inchi: 1S/C12H12O/c1-11(13)7-5-6-10-12-8-3-2-4-9-12/h2-10H,1H3/b7-5+,10-6+
    • InChI Key: PRNUCJKOERXADE-YLNKAEQOSA-N
    • SMILES: O=C(C)/C=C/C=C/C1C=CC=CC=1

Computed Properties

  • Exact Mass: 172.08886
  • Monoisotopic Mass: 172.089
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 207
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 2
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.7
  • Topological Polar Surface Area: 17.1A^2

Experimental Properties

  • Density: 1.009
  • Boiling Point: 317.1°C at 760 mmHg
  • Flash Point: 117.8°C
  • Refractive Index: 1.571
  • PSA: 17.07
  • LogP: 2.84500

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6-phenylhexa-3,5-dien-2-one Related Literature

Additional information on 6-phenylhexa-3,5-dien-2-one

Introduction to 6-phenylhexa-3,5-dien-2-one (CAS No. 29179-13-3)

6-phenylhexa-3,5-dien-2-one, identified by the Chemical Abstracts Service registry number CAS No. 29179-13-3, is a significant organic compound that has garnered attention in the field of synthetic chemistry and pharmaceutical research. This molecule, featuring a conjugated system with a phenyl group and a diene backbone, exhibits unique structural and electronic properties that make it a valuable scaffold for developing novel bioactive molecules.

The compound’s structure consists of a hexadienone core substituted with a phenyl ring at the sixth carbon position. This arrangement confers distinct reactivity patterns, making it a versatile intermediate in organic synthesis. The presence of the carbonyl group at the second carbon and the conjugated double bonds at positions 3 and 5 contribute to its ability to participate in various chemical reactions, including Diels-Alder cycloadditions, Michael additions, and oxidation processes.

In recent years, 6-phenylhexa-3,5-dien-2-one has been explored as a building block in medicinal chemistry due to its potential to serve as a precursor for more complex pharmacophores. The phenyl ring introduces hydrophobicity and electronic modulation, while the diene system allows for further functionalization. Such features are particularly attractive for designing molecules with targeted biological activity.

One of the most compelling aspects of 6-phenylhexa-3,5-dien-2-one is its utility in generating derivatives with enhanced biological properties. Researchers have leveraged its scaffold to develop compounds with antimicrobial, anti-inflammatory, and even anticancer potential. For instance, modifications at the phenyl ring or the diene positions can alter the molecule’s interactions with biological targets, leading to improved efficacy or selectivity.

The synthesis of 6-phenylhexa-3,5-dien-2-one typically involves multi-step organic transformations starting from readily available precursors. Common synthetic routes include Friedel-Crafts alkylation followed by dehydrogenation or cross-coupling reactions to introduce the phenyl group. The precision required in these synthetic steps underscores the compound’s importance as a synthetic intermediate.

Recent advancements in computational chemistry have further highlighted the significance of 6-phenylhexa-3,5-dien-2-one. Molecular modeling studies suggest that its structure can be optimized to enhance binding affinity to specific protein targets. These insights have guided experimental efforts toward designing more potent derivatives with therapeutic applications.

The pharmacological profile of compounds derived from 6-phenylhexa-3,5-dien-2-one continues to be an area of active investigation. By systematically modifying its structure, researchers aim to uncover novel mechanisms of action and expand its therapeutic potential. This includes exploring its interactions with enzymes and receptors involved in various disease pathways.

The compound’s role in material science is also noteworthy. Its conjugated system and aromaticity make it suitable for applications in organic electronics, such as organic light-emitting diodes (OLEDs) and photovoltaic devices. The ability to fine-tune its electronic properties through structural modifications opens up possibilities for developing next-generation materials with improved performance.

In conclusion, 6-phenylhexa-3,5-dien-2-one (CAS No. 29179-13-3) is a multifaceted compound with broad applications across synthetic chemistry, pharmaceutical research, and materials science. Its unique structural features and reactivity patterns make it an invaluable tool for developing innovative solutions in these fields. As research progresses, the full potential of this molecule is expected to be realized through continued exploration and optimization.

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