SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 08: 1817 - 1821

DOI: https://doi.org/10.6023/cjoc201303003

Notes

Synthesis and Crystal Structure of 12-(2-Chlorophenyl)-7,11,13,16-tetraoxaspiro[5.2.5.2]cetane

  • Yuan Lin ,
  • Ou Guangchuan ,
  • Shi Jianghua ,
  • Zhang Min ,
  • Yuan Xianyou
Expand
  • Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou 425199

Received date: 2013-03-02

  Revised date: 2013-04-19

  Online published: 2013-04-24

Supported by

Project supported by the Construct Program of the Key Discipline in Hunan Province (No. 2011-76), the Science and Technology Planning Project of Hunan Province (No. 2013FJ3004), the Scientific Research Fund of Hunan Provincial Education Department (Nos. 13A030, 013B029), and the Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province (No. 2012-318)

Fold

Abstract

12-(2-Chlorophenyl)-7,11,13,16-tetraoxaspiro[5.2.5.2]cetane (2) was prepared by cyclohexanone and 5,5-bis(hydroxymethyl)-2-(2-chlorophenyl)-1,3-dioxane (1) which synthesized from the reaction of the o-chlorobenzaldehyde and pentaerythriol, or prepared by o-chlorobenzaldehyde and 9,9-bis(hydroxymethyl)-7,11-dioxaspiro[5,5]undecane (3) which synthesized from the reaction of the cyclohexanone and pentaerythriol. Compounds 1 and 2 were characterized by X-ray diffraction, elemental analysis, 1H NMR. Single crystal X-ray diffraction analyses reveal that compound 1 belongs to monoclinic system with space group P2(1)/n with a=0.56768(15) nm, b=0.9807(3) nm, c=2.1785(6) nm, a=90°, b=90.204(4)°, g=90°, V= 1.2128(5) nm3, Z=4, Dc=1.417 Mg/m3, μ=0.315 mm-1, F(000)=544. Compound 2 also belongs to monoclinic system with space group C2/c with a=1.5894(5) nm, b=1.5704(4) nm, c=2.8369(9) nm, a=90°, b=101.103(5)°, g=90°, V=6.948(4) nm3, Z=16, Dc=1.296 Mg/m3, μ=0.237 mm-1, F(000)=2880.

Key words： o-chlorobenzaldehyde; pentaerythriol; crystal structure; 1H NMR

Cite this article

Yuan Lin , Ou Guangchuan , Shi Jianghua , Zhang Min , Yuan Xianyou . Synthesis and Crystal Structure of 12-(2-Chlorophenyl)-7,11,13,16-tetraoxaspiro[5.2.5.2]cetane[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1817 -1821 . DOI: 10.6023/cjoc201303003

References

[1] Wang, Y. Y.; Gong, X. X.; Wang, Z. Z.; Dai, L. Y. J. Mol. Catal. A: Chem. 2010, 322, 7.
[2] Edizer, S.; Veronesi, B.; Karahan, O.; Aviyente, V.; Degirmenci, I.; Galbiati, A.; Pasini, D. Macromolecules 2009, 42, 1860.
[3] Wessig, P.; Mollnitz, K. J. Org. Chem. 2008, 73, 4452.
[4] Chen, W.; Meng, F. H.; Li, F.; Ji, S. J.; Zhong. Z. Y. Biomacromolecules 2009, 10, 1727.
[5] Wang, Y. Y.; Xu, Y. N.; Wang, Z. Z.; Dai, L. Y. Chin. Chem. Lett. 2010, 21, 524.
[6] Wang, G. W.; Yuan, X. Y.; Liu, Y. C.; Lei, X. G. J. Am. Oil Chem. Soc. 1994, 74, 727.
[7] Yuan, X. Y.; Yang, N. F.; Luo, H. A.; Liu, Y. J. Chin. J. Org. Chem. 2005, 25, 1049 (in Chinese).
(袁先友, 阳年发, 罗和安, 刘跃进, 有机化学, 2005, 25, 1049.)
[8] Barr, J.; Woodburn, K. W.; Ng, S. Y.; Shen, H. R.; Heller, J. Adv. Drug Delivery Rev. 2002, 54, 1041.
[9] Zhao, Y. M.; Wang, Z. Y.; Yang, F. J. Appl. Polym. Sci. 2005, 97, 195.
[10] Kricheldorf, H. R. Chemosphere 2001, 43, 49.
[11] Kim, K. S.; Lee, S. M.; Ryu, K. C.; Lee, K. S. Polym. Bull. 1995, 35, 57.
[12] Lakshmi, B.; Devi, A. P.; Nagarajan, M. J. Chem. Soc., Perkin Trans. 1 1997, 1495.
[13] Sun, X. Q.; Yu, S. L.; Li, Z. Y.; Yang, Y. J. Mol. Struct. 2010, 973, 152.
[14] Wang, X. Y.; Shi, J. H.; Zhang, M.; Ng, S. W. Acta Crystallogr. 2010, E62, o426.
[15] Yuan, X. Y.; Zhang, M.; Yuan, L. Chin. J. Org. Chem. 2007, 27, 1600 (in Chinese).
(袁先友, 张敏, 袁霖, 有机化学, 2007, 27, 1600.)
[16] Wang, G. W.; Yuan, X. Y.; Liu, Y. C.; Guo, Q. X. Indian J. Chem. Sect. B 1996, 35, 583.
[17] Yuan, X. Y.; Luo, H. A.; Yang, N. F.; Liu, Y. J. J. Hunan Univ. ( Nat. Sci.) 2006, 33, 99 (in Chinese).
(袁先友, 罗和安, 阳年发, 刘跃进, 湖南大学学报(自然科学版), 2006, 33, 99.)
[18] Sheldrick, G. M. SADABS, Program for the Absorption Correction, University of Göttingen, Germany, 2004.
[19] Sheldrick, G. M. SHELXS 97, Program for the Solution of Crystal Structure, University of Göttingen, Germany, 1997.
Options
Outlines

/

〈 〉