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2-Phenylbenzofuran

From Wikipedia, the free encyclopedia
Chemical compound
2-Phenylbenzofuran
Names
Preferred IUPAC name
2-Phenyl-1-benzofuran
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 654-035-7
  • InChI=1S/C14H10O/c1-2-6-11(7-3-1)14-10-12-8-4-5-9-13(12)15-14/h1-10H
    Key: HXMZLDUBSSPQIB-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C2=CC3=CC=CC=C3O2
Properties
C14H10O
Molar mass194.233 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302,H413
P264,P270,P273,P301+P317,P330,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

2-Phenylbenzofuran (2-phenyl-benzo[b]furan) is a chemical compound that has the molecular formula C14H10O. It is asubstituted benzofuran, with aphenyl group as thesubstituent.

Occurrence and synthesis

[edit]

2-Phenylbenzofuran is a natural product, and its derivatives (known as 2-phenylbenzofurans) have been isolated from various plants, such asArtocarpus pithecogallus,[2]legumes, andmulberries.[3][4]

Because there is a substituent at position 2, this benzofuran compound cannot be synthesized by thePerkin rearrangement from acoumarin. However, an alternate sequence has been demonstrated: treatment of 3-phenylcoumarin withaluminium hydride followed byDDQ:[3]

Applications

[edit]

2-Phenylbenzofuran and its derivatives have been the subject of research onantioxidant drugs,[5][2]butyrylcholinesterase inhibition,[6] andleishmaniasis treatment.[7]

References

[edit]
  1. ^"2-Phenylbenzofuran".PubChem. National Library of Medicine. September 8, 2005. RetrievedJune 10, 2024.
  2. ^abThuy, Phan Thi; Trang, Nguyen Van; Son, Ninh The (2020-02-07)."Antioxidation of 2-phenylbenzofuran derivatives: structural-electronic effects and mechanisms".RSC Advances.10 (11):6315–6332.Bibcode:2020RSCAd..10.6315T.doi:10.1039/C9RA10835A.ISSN 2046-2069.PMC 9049690.PMID 35496026.
  3. ^abKinoshita, Takeshi; Ichinose, Koji (2005-10-25)."A Short-Step Convenient Synthesis of 2-Phenylbenzofuran from 3-Phenylcoumarin"(PDF).ChemInform.36 (43).doi:10.1002/chin.200543118.ISSN 0931-7597.
  4. ^Wang, Wen; Wu, Dong-Ling; Liao, Sen-Tai; Fan, Chun-Lin; Guo-Qiang, Li; Zhang, Xian-Tao; Wang, Ying; Zhang, Xiao-Qi; Ye, Wen-Cai (May 2013). "Two 2-Phenylbenzofuran Derivatives fromMorus atropurpurea".Natural Product Communications.8 (5):599–600.doi:10.1177/1934578X1300800514.
  5. ^Borges, Rosivaldo S.; Aguiar, Christiane P. O.; Oliveira, Nicole L. L.; Amaral, Israel N. A.; Vale, Joyce K. L.; Chaves Neto, Antonio M. J.; Queiroz, Auriekson N.; da Silva, Albérico B. F. (August 2023). "Antioxidant capacity of simplified oxygen heterocycles and proposed derivatives by theoretical calculations".Journal of Molecular Modeling.29 (8).doi:10.1007/s00894-023-05602-8.ISSN 1610-2940.
  6. ^Delogu, Giovanna L.; Matos, Maria J.; Fanti, Maura; Era, Benedetta; Medda, Rosaria; Pieroni, Enrico; Fais, Antonella; Kumar, Amit; Pintus, Francesca (2016). "2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling".Bioorganic & Medicinal Chemistry Letters.26 (9):2308–2313.doi:10.1016/j.bmcl.2016.03.039.PMID 26995529.
  7. ^Agarwal, A.; Mishra, R.; Paliwal, S. (2012), Khemani, L. D.; Srivastava, M. M.; Srivastava, Shalini (eds.), "A QSAR Study Investigating the Potential Anti-Leishmanial Activity of Cationic 2-Phenylbenzofurans",Chemistry of Phytopotentials: Health, Energy and Environmental Perspectives, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 137–141,doi:10.1007/978-3-642-23394-4_30,ISBN 978-3-642-23393-7{{citation}}: CS1 maint: work parameter with ISBN (link)
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