Abstract
C19H18O4, orthorhombic, Pbcn, a = 21.1472(8) Å, b = 9.7978(4) Å, c = 14.5181(6) Å, V = 3008.1(2) Å3, Z = 8, Rgt(F) = 0.0520, wRref(F2) = 0.1194, T = 100(2).
The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Crystal: | Orange plate |
Size: | 0.56 × 0.17 × 0.09 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 1.0 cm−1 |
Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
2θmax, completeness: | 55°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 39151, 3461, 0.134 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2466 |
N(param)refined: | 214 |
Programs: | SHELX [22], Bruker programs [23] |
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
O1 | 0.45468(6) | 0.82075(12) | −0.11321(9) | 0.0172(3) |
O2 | 0.72991(6) | 1.06912(13) | −0.11627(9) | 0.0207(3) |
O3 | 0.36151(6) | 0.37388(14) | 0.36125(9) | 0.0197(3) |
O4 | 0.28832(6) | 0.58164(13) | 0.31800(9) | 0.0232(3) |
C1 | 0.49596(9) | 0.81438(17) | −0.05242(12) | 0.0142(4) |
C2 | 0.55753(9) | 0.88251(17) | −0.06542(12) | 0.0147(4) |
C3 | 0.57352(9) | 0.93631(17) | −0.15192(12) | 0.0155(4) |
H3A | 0.5446 | 0.9309 | −0.2000 | 0.019* |
C4 | 0.63112(9) | 0.99665(19) | −0.16657(13) | 0.0173(4) |
H4A | 0.6414 | 1.0304 | −0.2245 | 0.021* |
C5 | 0.67441(9) | 1.00737(18) | −0.09393(13) | 0.0167(4) |
C6 | 0.65949(9) | 0.95551(18) | −0.00765(13) | 0.0155(4) |
H6A | 0.6882 | 0.9633 | 0.0405 | 0.019* |
C7 | 0.60138(9) | 0.89180(17) | 0.00671(12) | 0.0150(4) |
C8 | 0.58494(9) | 0.83213(19) | 0.09932(13) | 0.0179(4) |
H8A | 0.5619 | 0.8992 | 0.1352 | 0.021* |
H8B | 0.6235 | 0.8101 | 0.1323 | 0.021* |
C9 | 0.54469(9) | 0.70305(19) | 0.08894(13) | 0.0178(4) |
H9A | 0.5692 | 0.6325 | 0.0586 | 0.021* |
H9B | 0.5325 | 0.6697 | 0.1493 | 0.021* |
C10 | 0.48615(9) | 0.73407(17) | 0.03296(13) | 0.0155(4) |
C11 | 0.42684(9) | 0.69864(17) | 0.05672(12) | 0.0158(4) |
H11A | 0.3943 | 0.7351 | 0.0213 | 0.019* |
C12 | 0.40819(9) | 0.60866(18) | 0.13255(12) | 0.0158(4) |
C13 | 0.44199(9) | 0.49039(18) | 0.15217(13) | 0.0180(4) |
H13A | 0.4763 | 0.4663 | 0.1156 | 0.022* |
C14. | 0.42482(9) | 0.40813(18) | 0.22580(13) | 0.0168(4) |
H14A | 0.4469 | 0.3276 | 0.2368 | 0.020* |
C15 | 0.37567(9) | 0.44399(18) | 0.28277(13) | 0.0154(4) |
C16 | 0.33833(9) | 0.55846(18) | 0.26053(13) | 0.0160(4) |
C17 | 0.35452(9) | 0.63824(18) | 0.18579(13) | 0.0164(4) |
H17A | 0.3294 | 0.7128 | 0.1705 | 0.020* |
C18 | 0.77579(10) | 1.0899(2) | −0.04455(14) | 0.0247(5) |
H18A | 0.8132 | 1.1303 | −0.0702 | 0.037* |
H18B | 0.7863 | 1.0037 | −0.0171 | 0.037* |
H18C | 0.7585 | 1.1494 | 0.0015 | 0.037* |
C19 | 0.24712(10) | 0.6916(2) | 0.29427(15) | 0.0257(5) |
H19A | 0.2121 | 0.6937 | 0.3363 | 0.039* |
H19B | 0.2317 | 0.6789 | 0.2327 | 0.039* |
H19C | 0.2698 | 0.7763 | 0.2979 | 0.039* |
H1O3 | 0.3905(12) | 0.308(3) | 0.3694(17) | 0.049(8)* |
Source of material
To a stirred solution of 6-methoxy-1-tetralone (5 g, 0.0028 mol) in conc. HCl (28 mL) and glacial acetic acid (28 mL) at 0 °C, vanillin (4.3 g, 0.0028 mol) was added. The resulting mixture was further stirred at this temperature for 3 h, then at room temperature for 18 h. Diethyl ether was added and the ethereal layer was discarded. The remaining residue was treated with a water/ice mixture. The separated solid was filtered off and recrystallized from ethanol/ petroleum ether to afford the title compound (50%) as red crystals, m.p. 110–115 °C; γmaxIR (KBr)/cm−1 3431, 3177, 2940, 2838, 1638, 1597, 1559, 1520, 1443, 1425, 1390, 1317, 1253, 1165; 1H-NMR (400 MHz; CDCl3) δH: 2.92 (2 H, t, J 6.0, CH2), 3.13 (2 H, app. td, J 6.0, 1.7, CH2), 3.87 (3H, s, OCH3), 3.92 (3H, s, OCH3), 6.70 (1H, d, J 2.6, CH—Ph-tetralone), 6.87 (1H, dd, J 8.5, 2.6, CH—Ph-tetralone), 6.96–6.95 (2H, m, 2 × CH—Ph-vanillin), 7.02(1H, dd, J 7.7, 1.7, CH—Ph-vanillin), 7.78 (1H, s, CH = CqCO), 8.10 (1H, d, J 8.5, CH—Ph-tetralone); 13C-NMR (100 MHz; CDCl3) δH: 27.28 (CH2), 29.18 (CH2), 55.40 (OCH3), 55.94 (OCH3), 112.21, 112.73, 113.21, 114.39, 123.64, 127.14, 128.32, 130.66, 133.70, 136.33, 145.51, 146.24, 163.46 (6 × CH—Ph-tetralone and CH—Ph, 6 × Cq-Ph-tetralone and Cq-Ph), 186.71 (C = O); δC (100 MHz; CDCl3) 27.28 (CH2), 29.18 (CH2), 55.40 (OCH3), 55.94 (OCH3), 112.21, 112.73, 113.21, 114.39, 123.64, 127.14, 128.32, 130.66, 133.70, 136.33, 145.51, 146.24, 163.46 (14 × CH-Ar, Cq-Ar and CH = Cq CO), 186.71 (C = O).
Experimental details
Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C) except for methyl hydrogen atoms. The H atoms of the methyl group were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density with Uiso(H) set to 1.5Ueq(C).
Discussion
2-Arylidene-1-tetralones contain the α,β-unsaturated enone fragment. This moiety is a characteristic functionality of biologically and synthetically important compounds known as chalcones. This synthon is considered as a versatile building block that can be used to construct heterocyclic rings having one or more heteroatoms and of different ring sizes such as 2-pyrazoline [1], pyrimidine [2, 3] , pyran, and isooxazoline [4]. Generally chalcones and their analogs are prepared by Claisen-Schmidt reactions under basic conditions using bases such as sodium hydroxide or potassium hydroxide [5], lithium hydroxide [6] and piperidine [7]. Acid catalyzed synthesis is also well established using p-toluene sulfonic acid under focused microwave irradiation [8], thionyl chloride [9], dry hydrochloric acid and borontrifluoride-etherate [10]. Some chalcones are known for their biological activities as they exhibit cytotoxic [11], antibacterial [12], antifungal [13], antimalarial and antitubercular [14], anti-inflammatory [15], antimalarial [16], antiviral [17], tyrosinase inhibitor [18], antiallergenic [19], antioxidant [20] and antihyperglycemic [21] activities.
The asymmetric unit cell of the titled compound contains one independent molecule. The bond length of C10—C11 is 1.346(3) Å, which are typical C = C double bond and the configuration around this double bond is trans. The molecules are connected in the crystal via intermolecular hydrogen bonds: O3—H1O3⋯O1i, symmetry code: (i) x, − y + 1, z + 1/2 forming chains along the c axis of the choosen unit cell. Additionally, non-classical hydrogen bonds may contribute to the stability of the packing.
Acknowledgements
The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding this Research Group No. RG-1435-083.
References
1 Ziani, N.; Lamara, K.; Sid, A.; Willem, Q.; Dassonneville, B.; Demonceau, A.: Synthesis of pyrazoline derivatives from the 1,3-dipolar cycloadditions using α, β-unsaturated cyclohexanone derivatives. Eur. J. Chem. 4 (2013) 176–179.10.5155/eurjchem.4.2.176-179.757Search in Google Scholar
2 Kachroo, M.; Panda, R.; Yadav, Y.: Synthesis and biological activities of some new pyrimidine derivatives from chalcones. Der Pharms Chem. 6 (2014) 352–359.Search in Google Scholar
3 Suwito, H.; Mustofa, J.; Kristanti, A. N.; Puspaningsih, N. N. T.: Chalcones: synthesis, structure diversity and pharmacological aspects. J. Chem. Pharm. Res. 6 (2014) 1076–1088.Search in Google Scholar
4 Sharma, B. K.; Ameta, S. C.; Dwivedi, V. K.: Ecofriendly synthesis of chalcones and their 2-pyrazoline and isoxazolines derivatives as potential microbial agents. Int. J. Chem. Sci. 12 (2014) 1121–1134.Search in Google Scholar
5 Asiri, A. M.; Khan, S. A.: Synthesis and anti-bacterial activities of a bis-chalcone derived from thiophene and its bis-cyclized products. Molecules 16 (2011) 523–531.10.3390/molecules16010523Search in Google Scholar PubMed PubMed Central
6 Panigrahi, N.; Ganguly, S.; Panda, J.; Praharsha, Y.: Ultrasound assisted synthesis and antimicrobial evaluation of novel thiophene chalcone derivatives. Chem. Sci. Trans. 3 (2014) 1163–1171.Search in Google Scholar
7 Trivedi, J. C.; Bariwal, J. B.; Upadhyay, K. D.; Naliapara, Y. T.; Joshi, S. K.; Pannecouque, C. C.; Clercq, E. D.; Shah, A. K.: Improved and rapid synthesis of new coumarinyl chalcone derivatives and their antiviral activity. Tetrahedron Lett. 48 (2007) 8472–8474.10.1016/j.tetlet.2007.09.175Search in Google Scholar
8 Gall, E. L.; Texier-Boullet, F.; Hamelin, J.: Simple access to α, β unsaturated ketones by acid-catalyzed solvent-free reactions. Synth. Commun. 29 (1999) 3651–365710.1080/00397919908086000Search in Google Scholar
9 Jayapal, M. R.; Prasad, K. S.; Sreedhar, N. Y. J.: Synthesis and characterization of 2, 4-dihydroxy substituted chalcones using aldol condensation by SOCl2/EtOH. Chem. Pharm. Res. 2 (2010) 127–132.Search in Google Scholar
10 Narender, T.; Reddy, K. P.: A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate. Tetrahedron Lett. 48 (2007) 3177–3180.10.1016/j.tetlet.2007.03.054Search in Google Scholar
11 Syam, S.; Abdelwahab, S. I.; Al-Mamary, M. A.; Mohan, S.: Synthesis of chalcones with anticancer activities. Molecules 17 (2012) 6179–6195.10.3390/molecules17066179Search in Google Scholar PubMed PubMed Central
12 Chikhalia, K. H.; Patel, M. J.; Vashi, D. B.: Design, synthesis and evaluation of novel quinolyl chalcones as antibacterial agents. ARKIVOC xiii (2008) 189–197.10.3998/ark.5550190.0009.d21Search in Google Scholar
13 Tailor, N. K.: Synthesis and antifungal activity of certain chalcones and their reduction. Indo Global J. Pharm. Sci. 4 (2014) 25–28.10.35652/IGJPS.2014.120Search in Google Scholar
14 Hans, R. H.; Guantai, E. M.; Lategan, C.; Smith, P. J.; Wan, B.; Franzblau, S. G.; Gut, J.; Rosenthal, P. J.; Chibale, K.: Synthesis, antimalarial and antitubercular activity of acetylenic chalcones. Bioorg. Med. Chem. Lett. 20 (2010) 942–944.10.1016/j.bmcl.2009.12.062Search in Google Scholar PubMed
15 Nowakowska, Z.: A review of anti-infective and anti-inflammatory chalcones. Eur. J. Med. Chem. 42 (2007) 125–137.10.1016/j.ejmech.2006.09.019Search in Google Scholar PubMed
16 Li, R.; Kenyon, G.; Cohen, F. E.; Chen, X.; Gong, B.; Dominguez, J. N.; Davidson, E.; Kurzban, G.; Miller, R. E.; Nuzum, E. O.: In vitro antimalarial activity of chalcones and their derivatives. J. Med. Chem. 38 (1995) 5031–5037.10.1021/jm00026a010Search in Google Scholar PubMed
17 Biradar, J. S.; Sasidhar, B. S.; Parveen, R.: Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. Eur. J. Med. Chem. 45 (2010) 4074–4078.10.1016/j.ejmech.2010.05.067Search in Google Scholar PubMed
18 Nerya, O.; Musa, R.; Khatib, S.; Tamir, S.; Vaya, J.: Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers. Phytochemistry 65 (2004) 1389–1395.10.1016/j.phytochem.2004.04.016Search in Google Scholar PubMed
19 Yamamoto, T.; Yoshimura, M.; Yamaguchi, F.; Kouchi, T.; Tsuji, R.; Saito, M.; OBata, A.; Kikuchi, M.: Anti-allergic activity of naringenin chalcone from a tomato skin extract. Biosci. Biotechnol. Biochem. 68 (2004) 1706–1711.10.1271/bbb.68.1706Search in Google Scholar PubMed
20 Murti, Y.; Goswami, A.; Mishra, P.: Synthesis and antioxidant activity of some chalcones and flavanoids. Int. J. PharmTech. Res. 5 (2013) 811–818.Search in Google Scholar
21 Satyanarayana, M.; Tiwari, P.; Tripathi, B. K.; Srivastava, A. K.; Pratap, R.: Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines. Bioorg. Med. Chem. 12 (2004) 883–889.10.1016/j.bmc.2003.12.026Search in Google Scholar PubMed
22 Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed
23 Brucker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, WI, USA, 2009.10.1097/IAE.0b013e3181ad255fSearch in Google Scholar PubMed
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