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| Synthesis,and Experimental and Theoretical Characterization of 3-(4-(Dimethylamino) benzylidene) -1,5-dioxaspiro [5.5]undecane-2,4-dione |
| ZENG Wu-Lan;CAI Xue;GUO Huan-Mei |
| Microscale Science Institute, Department of Chemistry, Chemical Engineering and Environmental Engineering, Weifang University, Weifang 261061, China |
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Abstract
The title molecule, 3-(4-(dimethylamino)benzylidene)-1,5-dioxaspiro[5.5] unde- cane-2,4-dione (I), was synthesized and characterized by elemental analysis, IR, UV-vis spectra and X-ray diffraction analysis. The compoundbelongs to the triclinic system, space group Pī with α = 6.3640(6), b = 7.7404(8), c = 16.2890(18) Å, α = 86.860(2), β = 85.837(2),γ = 79.6720(10)º, V = 786.60(14)Å3, Dc = 1.331 g/cm3, and F(000) =336. Geometrical structure of the title compound was optimized by density functional theory (DFT) using B3LYP method with 6-31G** as the basis set. The vibrational frequencies were calculated by the DFT method and the results are consistent with the observed frequencies. The electronic absorption spectra were studied with the time- dependent density functional theory (TD-DFT), showing the calculation results in good agreement with the corresponding experimental data.
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Received: 11 March 2013
Published: 10 September 2013
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| Fund:Project supported by the Natural Science Foundation of Shandong Province (Nos. ZR2010CL011 and ZR2010BM033) |
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Corresponding Authors:
曾伍兰:wulanzeng@163.com
E-mail: wulanzeng@163.com
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| About author:: 曾伍兰:wulanzeng@163.com |
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(1) Liang, Y.; Guo, J. J.; Liu, X. M.; Wei, R. B. Chiral separation of spiro-compounds and determination configuration.
Chem. Res. Chin. Univ. 2008, 24, 441–444.
(2) Lippa, B.; Pan, G.; Corbett, M.; Li, C.; Kauffman, G. S.; Pandit, J.; Robinson, S.; Wei, L.; Kozina, E.; Marr, E. S.; Borzillo, G.; Knauth, E.; Tobin, E. G. B.; Vincent, P.; Troutman, M.; Baker, D.; Rajamohan, F.; Kakar, S.; Clark, T.; Morris, J. Synthesis and structure based optimization of novel akt inhibitors. Bioorg. Med. Chem. lett. 2008, 18, 3359–3363.
(3) Pradhan, R.; Patra, M.; Behera, A. K.; Mishra, B. K.; Behera, R. K. A synthon approach to spiro compounds. Tetra. 2006, 62, 779–828.
(4) Kongsaeree, P.; Prabpai, S.; Sriubolmas, N.; Vongvein, C.; Wiyakrutta, S. Antimalarial dihydroisocoumarins produced by geotrichum sp., an endophytic fungus of crassocephalum crepidioides. J. Nat. Prod. 2003, 66, 709–711.
(5) Jiang, Y.; Xue, S.; Li, Z.; Deng, J.; Mi, A.; Chan, A. S. C. Asymmetric hydroformylation of styrene catalyzed by chiral spiro diphosphite-rhodium(I) complexes. Tetra. 1998, 9, 3185–3189.
(6) Kim, J. H.; Jeon, Y. M.; Jang, J. G.; Ryu, S.; Chang, H. J.; Lee, C. W.; Kim, J. W.; Gong, M. S.
Blue oleds utilizing spiro[fluorine-7,9΄-benzofluorene]-type compounds as hosts and dopants. Bull. Korean Chem. Soc. 2009, 30, 647–652.
(7) Zvonok, A. M.; Okaev, E. B. Chemical reaction between piperidine-4-spiro-2΄-oxiranes and nucleophilic reagents.
Heterocycl. Compd. 1993, 29, 1291–1295.
(8) McCallum, J. E. B.; Kuniyoshi, C. Y.; Foote, C. S. Characterization of 5-hydroxy-8-oxo-7,8-dihydroguanosine in the photosensitized oxidation of 8-oxo-7,8-dihydroguanosine and its rearrangement to spiroiminodihydantoin. J. Am. Chem. Soc. 2004, 126, 16777–16782.
(9) Xie, L. H.; Liu, F.; Tang, C.; Hou, X. Y.; Hua, Y. R.; Fan, Q. L.; Huang, W. Unexpected one-pot method to synthesize spiro[fluorene-9,9‘-xanthene] building blocks for blue-light-emitting materials. Org. Lett. 2006, 8, 2787–2790.
(10) Liu, F.; Xie, L. H.; Tang, C.; Liang, J.; Chen, Q. Q.; Peng, B.; Wei, W.; Cao, Y.; Huang, W. Facile synthesis of spirocyclic aromatic hydrocarbon derivatives based on o-halobiaryl route and domino reaction for deep-blue organic semiconductors. Org. Lett. 2009, 11, 3850–3853.
(11) Zeng, W. L.; Li, Y. F.; Liu, Y.; Jian, F. F. Crystal structure of 1,5-dioxaspiro[5.5] undecane-2,4-dione, C9H12O4. Z.
Kristallogr. NCS 2010, 225, 498–500.
(12) Zeng, W. L. Synthesis and crystal structure of 3-(3,4-dimethylbenzylidene)-1,5-dioxaspiro [5.5]undecane-2,4-dione.
Asian J. Chem. 2011, 23, 4145–4147.
(13) Zeng, W. L.; Meng, Q. G.; Guo, H. M.; Zhang, L.; Jian, F. F. Syntheses and crystal Structures of two novel spiro compounds
containing 1,5-dioxaspiro[5.5]undecane-2,4-dione. Chin. J. Struct. Chem. 2010, 29, 696–699.
(14) Sheldrick, G. M. A short history of shelx. Acta Cryst. 2008, A64, 112–122.
(15) Siemens, Area Detector Control and Integration Software, USA 1996.
(16) Becke, A. D. A new mixing of hartree-fock and local density-functional theories. J. Chem. Phys. 1993, 98, 1372–1377.
(17) Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. Using redundant internal coordinates to optimize equilibrium geometries and transition states. J. Comput. Chem. 1996, 17, 49–56.
(18) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, J.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci,B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima,T.; Honda,Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian03, Revision C.01. Inc., Wallingford, CT 2004.
(19) Runge, E.; Gross, E. K. U. Density-functional theory for time-dependent systems. Phys. Rev. Lett. 1984, 52, 997–1000.
(20) Petersilka, M.; Gossmann, U. J.; Gross, E. K. U. Excitation energies from time-dependent density-functional theory.
Phys. Rev. Lett. 1966, 76, 1212–1215.
(21) Bauernschmitt, R.; Ahlrichs, R. Treatment of electronic excitations within the adiabatic approximation of time
dependent density functional theory. Chem. Phys. Lett. 1996, 256, 454–464.
(22) Zeng, W. L. Jian, F. F. 3-(2-Furylmethylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione. Acta Cryst. 2009, E65, o1875.
(23) Cremer, D.; Pople, J. A. A general definition of ring puckering coordinates. J. Am. Chem. Soc. 1975, 97, 1354–1358.
(24) Frish, A.; Nielsen, A. B.; Aholder, A. J. Gaussview Users Manual, Gaussian, inc., pittsburg, PA 2000.
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2013, Vol. 32 
