Citation: Hui-Juan LI, Zai-Gang LUO, Xiu-Xiu WANG. Crystal Structure and Thermal Property of 4-(3-Chlorophenyl)-3-isopropyl-1-methyl-3, 4-dihydroquinolin-2(1H)-one[J]. Chinese Journal of Structural Chemistry, ;2020, 39(5): 913-917. doi: 10.14102/j.cnki.0254-5861.2011-2565 shu

Crystal Structure and Thermal Property of 4-(3-Chlorophenyl)-3-isopropyl-1-methyl-3, 4-dihydroquinolin-2(1H)-one

Hui-Juan LI ^{a, b,,} ,
Zai-Gang LUO ^b,, ,
Xiu-Xiu WANG ^b

a.
Department of Pharmaceutical Engineering, Bengbu Medical College, Bengbu 233030, China
b.
College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, China

Corresponding author: Hui-Juan LI, 18949670601@163.com Zai-Gang LUO, luozi139@163.com
Received Date: 7 August 2019
Accepted Date: 18 November 2019

Fund Project: the Natural Science Research Projects in Colleges and Universities of Anhui Province KJ2019A0116Natural Science Foundation of Anhui Province 1608085MB38

Figures(3)

The target compound (C₁₉H₂₀ClNO) was structurally determined by single-crystal X-ray diffraction. The crystal is in monoclinic system, space group P2₁/n with a = 9.2365(2), b = 12.1241(3), c = 14.9960(4) Å, β = 106.589(3)°, C₁₉H₂₀ClNO, M_r = 313.81, D_c = 1.295 g/cm³, V = 1609.42(7) Å³, Z = 4, F(000) = 664, µ(MoKa) = 2.097 mm^-1, T = 200(10) K, 2813 independent reflections with 2533 observed ones (I > 2σ(I)), R = 0.0389 and wR = 0.1057 with GOF = 1.043 (R = 0.0423 and wR = 0.1083 for all data). The 3, 4-dihydroquinolin-2(1H)-one moiety maintains thermodynamically stable trans configuration. The decomposition mechanism of compound 3 is complex by thermal analysis.
- 3,4-dihydroquinolin-2(1H)-one,
- crystal structure,
- thermal property
1. [1]
  Sridharan, V.; Suryavanshi, P. A.; Menéndez, J. C. Advances in the chemistry of tetrahydroquinolines. Chem. Rev. 2011, 111, 7157–7259. doi: 10.1021/cr100307m
2. [2]
  Alabaster, C. T.; Bell, A. S.; Campbell, S. F.; Ellis, P.; Henderson, C. G.; Morris, D. S.; Roberts, D. A.; Ruddock, K. S.; Samuels, G. M. R.; Stefaniak, M. H. 2(1H)-Quinolinones with cardiac stimulant activity. 2. Synthesis and biological activities of 6-(N-linked, five-membered heteroaryl) derivatives. J. Med. Chem. 1989, 32, 575–583. doi: 10.1021/jm00123a011
3. [3]
  Joseph, B.; Darro, F.; Behard, A.; Lesur, B.; Collignon, F.; Decaestecker, C.; Frydman, A.; Guillaumet, G.; Kiss, R. 3-Aryl-2-quinolone derivatives: synthesis and characterization of in vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration. J. Med. Chem. 2002, 45, 2543–2555. doi: 10.1021/jm010978m
4. [4]
  Patel, M.; McHugh, R. J.; Cordova, B. C.; Klabe, R. M.; Bacheler, L. T.; Erickson-Viitanen, S.; Rodger, J. D. Structure based design, synthesis and SAR of cyclic hydroxyethylamine (HEA) BACE-1 inhibitors. Bioorg. Med. Chem. Lett. 2011, 11, 1942–1947.
5. [5]
  Li, K.; Foresee, L. N.; Tunge, J. A. Trifluoroacetic acid-mediated hydroarylation: synthesis of dihydrocoumarins and dihydroquinolones. J. Org. Chem. 2005, 70, 2881–2883. doi: 10.1021/jo0477650
6. [6]
  Tsuritani, T.; Yamamoto, Y.; Kawasaki, M.; Mase, T. Novel approach to 3, 4-dihydro-2(¹H)-quinolinone derivatives via cyclopropane ring expansion. Org. Lett. 2009, 11, 1043–1045. doi: 10.1021/ol802669r
7. [7]
  Tsubusaki, T.; Nishino, H. Manganese(Ⅲ)-mediated facile synthesis of 3, 4-dihydro-2(1H)-quinolinones: selectivity of the 6-endo and 5-exo cyclization. Tetrahedron 2009, 65, 9448–9459. doi: 10.1016/j.tet.2009.08.068
8. [8]
  François, X. F.; Jérôme, C.; Cécile, Z.; Eric, F. Preparation of 2-quinolones by sequential Heck reduction-cyclization (HRC) reactions by using a Multitask palladium catalyst. Chem. Eur. J. 2009, 15, 7238–7245. doi: 10.1002/chem.200900583
9. [9]
  Zhou, W.; Zhang, L. R.; Jiao, N. The tandem reaction combining radical and ionic processes: an efficient approach to substituted 3, 4-dihydroquinolin-2-ones. Tetrahedron 2009, 65, 1982–1987. doi: 10.1016/j.tet.2009.01.027
10. [10]
  Sibi, M. P.; Manyem, S.; Zimmerman, J. Enantioselective radical processes. Chem. Rev. 2003, 103, 3263–3296. doi: 10.1021/cr020044l
11. [11]
  Deb, A.; Manna, S.; Modak, A.; Patra, T.; Maity, S.; Maiti, D. Oxidative trifluoromethylation of unactivated olefins: an efficient and practical synthesis of α-trifluoromethyl-substituted ketones. Angew. Chem., Int. Ed. 2013, 52, 9747–9750. doi: 10.1002/anie.201303576
12. [12]
  Li, Z. D.; Song, L. Y.; Li, C. Z. Silver-catalyzed radical aminofluorination of unactivated alkenes in aqueous media. J. Am. Chem. Soc. 2013, 135, 4640–4643. doi: 10.1021/ja400124t
13. [13]
  Pan, C. D.; Zhang, H. L.; Han, J.; Cheng, Y. X.; Zhu, C. J. Metal-free radical oxidative decarboxylation/cyclization of acyl peroxides and 2-isocyanobiphenyls. Chem. Commun. 2015, 51, 3786–3788. doi: 10.1039/C4CC10015H
14. [14]
  Zhou, S. L.; Guo, L. N.; Wang, S.; Duan, X. H. Copper-catalyzed tandem oxidative cyclization of cinnamamides with benzyl hydrocarbons through cross-dehydrogenative coupling. Chem. Commun. 2014, 50, 3589−3591. doi: 10.1039/c4cc00637b
15. [15]
  Ling, A.; Zhang, L. Z.; Tan, R. X.; Liu, Z. Q. Molecular oxygen-promoted general and site-specific alkylation with organoboronic acid. J. Org. Chem. 2018, 83, 14489−14497. doi: 10.1021/acs.joc.8b02277
16. [16]
  Wang, K. C.; Chen, X.; Yuan, M.; Yao, M.; Zhu, H.; Xue, Y.; Luo, Z.; Zhang, Y. Silver-mediated cyanomethylation of cinnamamides by direct C(sp³)–H functionalization of acetonitrile. J. Org. Chem. 2018, 83, 1525−1531. doi: 10.1021/acs.joc.7b02585
17. [17]
  Gao, F.; Yang, C.; Gao, G. L.; Zheng, L. W.; Xia, W. J. Visible-light induced trifluoromethylation of N-arylcinnamamides for the synthesis of CF₃-containing 3, 4-disubstituted dihydroquinolinones and 1-azaspiro[4.5]decanes. Org. Lett. 2015, 17, 3478−3481. doi: 10.1021/acs.orglett.5b01530
18. [18]
  Mai, W. P.; Sun, G. C.; Wang, J. T.; Song, G.; Mao, P.; Yang, L. R.; Yuan, J. W.; Xiao, Y. M.; Qu, L. B. Silver-catalyzed radical tandem cyclization: an approach to direct synthesis of 3-acyl-4-arylquinolin-2(1H)-ones. J. Org. Chem. 2014, 79, 8094−8102. doi: 10.1021/jo501301t
19. [19]
  Zhang, H. L.; Gu, Z. X.; Li, Z. Y.; Pan, C. D.; Li, W. P.; Hu, H. W.; Zhu, C. J. Silver-catalyzed cascade radical cyclization: a direct approach to 3, 4-disubstituted dihydroquinolin-2(1H)-ones through activation of the P–H bond and functionalization of the C(sp²)–H bond. J. Org. Chem. 2016, 81, 2122−2127. doi: 10.1021/acs.joc.5b01879
20. [20]
  Cui, Z.; Du, D. M. FeCl₂-catalyzed decarboxylative radical alkylation/cyclization of cinnamamides: access to dihydroquinolinone and pyrrolo[1, 2-a]indole analogues. J. Org. Chem. 2018, 83, 5149−5159. doi: 10.1021/acs.joc.8b00511
21. [21]
  Yang, L.; Lu, W.; Zhou W.; Zhang, F. Metal-free cascade oxidative decarbonylative alkylarylation of acrylamides with aliphatic aldehydes: a convenient approach to oxindoles via dual C(sp²)–H bond functionalization. Green Chem. 2016, 18, 2941–2945. doi: 10.1039/C6GC00362A
22. [22]
  Luo, Z. G.; Han, X. X.; Fang, Y. Y.; Liu, P.; Feng, C. T.; Li, Z.; Xu, X. M. Copper-catalyzed decarboxylative and oxidative decarbonylative cross-coupling between cinnamic acids and aliphatic aldehydes. Org. Chem. Front. 2018, 5, 3299–3305. doi: 10.1039/C8QO00927A
23. [23]
  Xu, X. M; Luo, Z. G.; Liu, C. F.; Wang, X. X.; Deng, L. D.; Gao, J. Metal-free synthesis of 3, 4-dihydroquinolin-2(1H)‑ones via cascade oxidative decarbonylative radical alkylation/cyclization of cinnamamides with aliphatic aldehydes. Asian J. Org. Chem. 2019, 8, 1903–1906. doi: 10.1002/ajoc.201900424
24. [24]
  Bruker 2000, SMART (Version 5.0), SAINT-plus (Version 6), SHELXTL (Version 6.1), and SADABS (Version 2.03); Bruker AXS Inc. : Madison, WI.
25. [25]
  Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution. University of Göttingen, Germany 1997.
26. [26]
  Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure. University of Göttingen: Göttingen, Germany 1997.
27. [27]
  Chen, C. Y.; Hu, J. S.; Chai, F. F.; Xie, K. Y.; Zhang, X. M.; Shi, J. J. Synthesis, crystal structure and properties of ethyl 3, 9-dimethyl-7-phenyl-6H-dibenzo[b, d]pyran-6-one-8-carboxylate. Chin. J. Struct. Chem. 2014, 33, 395−400.
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