2-Phenylbenzofuran

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2-Phenylbenzofuran
2-Phenylbenzofuran.svg
Names
Preferred IUPAC name
2-Phenyl-1-benzofuran
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 654-035-7
PubChem CID
  • 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 mass 194.233 g·mol−1
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H302, H413
P264, P270, P273, P301+P317, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Contents

Occurrence and synthesis

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

Because there is a substituent at position 2, this benzofuran compound cannot be synthesized by the Perkin rearrangement from a coumarin. However, an alternate sequence has been demonstrated: treatment of 3-phenylcoumarin with aluminium hydride followed by DDQ: [3]

3mthcmrn-2phenbenzf.png

Applications

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

References

  1. ↑ "2-Phenylbenzofuran". PubChem. National Library of Medicine. September 8, 2005. Retrieved June 10, 2024.
  2. 1 2 Thuy, 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. 1 2 Kinoshita, 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 from Morus 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
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