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Synthesis, Crystal Structure, and DFT Study of Ethyl 3-(2,3-Dihydrobenzofuran-5-yl)-2-propenoate

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Abstract

The target compound ethyl 3-(2,3-dihydrobenzofuran-5-yl)-2-propenoate was synthesized by a two-step reaction. A single crystal of this compound was grown in a suitable solvent system, the structure of this compound was confirmed by 1H and 13C NMR, MS, FT-IR, and X-ray single crystal diffraction methods. At the same time, conformational studies and crystallographic analysis of the structure were carried out. The Hirshfeld surface analysis method was used to analyze the intermolecular forces. The crystal structure of the target compound was optimized by density functional theory calculations. The crystal structure after X-ray crystal diffraction was compared with the crystal structure optimized by DFT calculation. The results showed that the single crystal structure determined by X-ray crystal diffraction was consistent with the molecular structure after DFT optimization. In addition, by further studying the molecular electrostatic potential and frontier molecular orbital of the target compound, the molecular physicochemical properties of the target compound are understood.

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REFERENCES

  1. Xu, Z., Zhao, S.J., Lv, Z.S., Feng, L.S., Wang, Y.L., Zhang, F., Bai, L.Y, and Deng, J.L., Eur. J. Med. Chem., 2019, vol. 162, p. 266. https://doi.org/10.1016/j.ejmech.2018.11.025

    Article  CAS  Google Scholar 

  2. Dong, M.Y., Zhang, Y., Jiang, H.Q., Ren, W.J., Xu, L.C., Zhang, Y.Q., and Liu, Y.H., Eur. J. Med. Chem., 2019, vol. 35, p. 5145. https://doi.org/10.1080/14786419.2020.1786827

    Article  CAS  Google Scholar 

  3. Thanika, P., Pawinee, J., Wisanu, M., Roonglawan, R., Sumalee, K., Stephen, G.P., and Thunwadee, L., Nat. Prod. Res., 2020, vol. 34, p. 1394. https://doi.org/10.1080/14786419.2018.1512990

    Article  CAS  Google Scholar 

  4. Kunwar, S., Lee, S.M., Kadayat, T.M., Shrestha, A., Park, P.H., and Lee, E.S., Bioorg. Med. Chem. Lett., 2022, vol. 73, p. 824. https://doi.org/10.1016/j.bmcl.2022.128921

    Article  CAS  Google Scholar 

  5. López-Frías, G., Camacho-Dávila, A.A., ChávezFlores, D., Zaragoza-Galán, G., and RamosSánchez, V.H., Molecules, 2015, vol. 20, p. 8654. https://doi.org/10.3390/molecules20058654

    Article  CAS  Google Scholar 

  6. Ha, H.J., Kang, D.W., Kim, H.M., Kang, J.M., Ann, J., Hyun, H.J., Lee, J.H., Kim, S.H., Kim, H., Choi, K., Hong, H.S., Kim, Y.H., Jone, D.G., and Lee, J., J. Med. Chem. 2018, vol. 61, p. 396. https://doi.org/10.1021/acs.jmedchem.7b00844

  7. Liang, Z., Xu, Z., Tian, Y., Guo, M.B., Su, X., and Guo, C., Molecules, 2016, vol. 21, p. 732. https://doi.org/10.3390/molecules21060732

    Article  CAS  Google Scholar 

  8. Gao, Y.T., Ma, C., Feng, X. Z., Liu, Y., and Hai, M.T.X., Chem. Biodivers., 2020, vol. 17, p. 346. https://doi.org/10.1002/cbdv.201900622

    Article  CAS  Google Scholar 

  9. Abdelhafez, O.M., Ali, H.I., Amin, K.M., Abdalla, M.M., and Ahmed, E.Y., RSC Adv., 2015, vol. 5, p. 25312. https://doi.org/10.1039/c4ra16228e

    Article  CAS  Google Scholar 

  10. Gao, S.Y., Qian, G.Y., Tang, H., Yang, Z., and Zhou, Q.H., ChemCatChem, 2019, vol. 11, p. 5762. https://doi.org/10.1002/cctc.201901355

    Article  CAS  Google Scholar 

  11. Ye, W.J., Chen, D.M., Wu, Q.M., Chen, Y.M., Yang, D.Z., Liao, T.H., and Zhou, Z.X., J. Struct. Chem., 2021, vol. 62, p. 1357. https://doi.org/10.1134/s0022476621090043

    Article  CAS  Google Scholar 

  12. Zhou, L.P., Qiu, F., Zhang, Z.F., Wang, C.M., Dong, Y.L., and Liu, J.P., J. Struct. Chem., 2020, vol. 61, p. 1111. https://doi.org/10.1134/s0022476620070148

    Article  CAS  Google Scholar 

  13. Chamberland, S., Ziller, J.W., and Woerpel, K.A., J. Am. Chem. Soc, 2005, vol. 127, p. 755. https://doi.org/10.1107/s2053229614024218

    Article  Google Scholar 

  14. Dai, H.Y., Yang, D.Z., Liao, W.P., Wu, F., Zhou, Z.X., and Huang, Z.Y., Russ. J. Gen. Chem., 2022, vol. 92, p. 438. https://doi.org/10.1134/s1070363222030112

  15. Wu, Q.M., Zheng, Z.P., Ye, W.J., Guo, Q., Liao, T.H., Yang, D.Z., and Zhou, Z.X., J. Struct. Chem., 2022, vol. 52, p. 1247. https://doi.org/10.1016/j.molstruc.2021.131367

    Article  CAS  Google Scholar 

  16. Im, G.Y.J., Bronner, S.M., Goetz, A.E., Paton, R.S., Cheong, P.H Y, Houk, K.N., and Garg, N.K., J. Am. Chem. Soc., 2010, vol. 132, p. 17933. https://doi.org/10.1021/ja1086485

  17. Deng, L.Y., Liao, T.H., Sun, H., Hu, W.Y., Zhou, Z.X., Zhao, C.S., and Pan, H.Y., Mol. Cryst. Liq. Cryst., 2022, vol. 737, p. 30. https://doi.org/10.1080/15421406.2021.2003952

    Article  CAS  Google Scholar 

  18. Wu, Q., Li, J.D., Liu, F.X., Xiao, J.C., Tang, Y.F., and Zi, Q.L., Russ. J. Coord. Chem., 2020, vol. 46, p. 37. https://doi.org/10.1134/s1070328420020086

    Article  CAS  Google Scholar 

  19. Liu, Y., Zheng, Z., Deng, H., Ren, Q., Zhou, Z., Zhao, C., and Chai, H., J. Struct. Chem., 2021, vol. 62, p. 1285. https://doi.org/10.1134/s0022476621080163

    Article  CAS  Google Scholar 

  20. Liang, S.Z., Hammond, G.B., and Bo, X., Eur. J. Med. Chem., 2017, vol. 23, p. 17850. https://doi.org/10.1080/15421406.2021.2003952

    Article  CAS  Google Scholar 

  21. Daoui, S., Çınar, E.B., El Kalai, F., Saddik, R., Dege, N., Karrouchi, K., and Benchat, N., Acta Cryst., 2019, vol. 75, p. 1880. https://doi.org/10.1107/s2056989019015147

  22. Fukui, K., Yonezawa, T., and Shingu, H.J., Polym. Sci., 1952, vol. 20, p. 722. https://doi.org/10.1021/ja1086485

    Article  CAS  Google Scholar 

  23. Dyachenko, I.V., Dyachenko, V.D., Yakushev, I.A., Khrustalev, V.N., and Nenaidenko, V.G., Russ. J. Org. Chem., 2020, vol. 56, p. 1669. https://doi.org/10.1134/s1070428020090262

    Article  CAS  Google Scholar 

  24. Pearson, R.G., Proc. Natl. Acad. Sci. U.S.A., 1986, vol. 83, p. 8440. https://doi.org/10.1073/pnas.83.22.8440

    Article  CAS  Google Scholar 

  25. Mckinnon, J.J., Fabbiani, F., and Spackman, M.A., Cryst. Growth Des, 2007, vol. 7, p. 755. https://doi.org/10.1021/cg060773k

    Article  CAS  Google Scholar 

  26. Roberto, G.S.B., J. Nat. Prod. 2005, vol. 66, p. 1577. https://doi.org/10.1021/np058254r

  27. Lin, W.Y., Yang, F., Duan, A.N.W., You, W., and Zhao, P.L., J. Struct. Chem, 2018, vol. 37, p. 1557. https://doi.org/10.14102/j.cnki.0254-5861

  28. Sheldrick, G.M., Acta Cryst. (C), 2015, vol. 71, p. 467. https://doi.org/10.1107/s2053229614024218

    Article  Google Scholar 

  29. Qin, Y., Long, D., Zhu, X., Zhou, Z., Chai, H., and Zhao, J. Struct. Chem., 2019, vol. 11, p. 1917. https://doi.org/10.1134/s0022476619120072

    Article  CAS  Google Scholar 

  30. Vieweg, N., Celik, M.A., Zakel, S., Gupta, V., Frenking, G., and Koch, M., J. Infrared Millim. Terahertz Waves, 2014, vol. 35, p. 478. https://doi.org/10.1007/s10762-014-0062-3

  31. Wandas, M., Lorenc, J., Kucharska, E., Ma̧czka, M., and Hanuza, J., J. Raman Spectrosc., 2008, vol. 39, p. 832. https://doi.org/10.1002/jrs.1922

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

This work has been awarded the Guizhou Provincial Natural Science Foundation ([2020]1Y393).

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Authors and Affiliations

  1. School of Pharmaceutical Sciences, Guizhou University, 550025, Guiyang, China

    L.-X. Ma, Y. Shi, J.-L. Li, Q. Guo, Z.-X. Zhou & Z.-Y. Huang

  2. Guizhou Engineering Laboratory for Synthetic Drugs, 550025, Guiyang, China

    L.-X. Ma, Y. Shi, J.-L. Li, Q. Guo, Z.-X. Zhou & Z.-Y. Huang

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  1. L.-X. Ma
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  2. Y. Shi
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  3. J.-L. Li
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Correspondence to Z.-Y. Huang.

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Ma, LX., Shi, Y., Li, JL. et al. Synthesis, Crystal Structure, and DFT Study of Ethyl 3-(2,3-Dihydrobenzofuran-5-yl)-2-propenoate. Russ J Gen Chem 92, 2880–2887 (2022). https://doi.org/10.1134/S1070363222120416

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