5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究

doi:10.6023/cjoc1106302

有机化学 ›› 2012, Vol. 32 ›› Issue (01): 104-112.DOI: 10.6023/cjoc1106302 上一篇下一篇

研究论文

5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究

傅建花, 汪朝阳, 霍景沛, 谭越河, 曾荣华

华南师范大学化学与环境学院广州 510006

收稿日期:2011-06-30 修回日期:2011-08-29 发布日期:2011-09-21
通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com
基金资助:
国家自然科学基金(No. 20772035)、广东省自然科学基金(No. 5300082)及广东省高等学校人才引进专项基金(No. [2011]431)资助项目.

Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines

Fu Jianhua, Wang Zhaoyang, Huo Jingpei, Tan Yuehe, Zeng Ronghua

School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received:2011-06-30 Revised:2011-08-29 Published:2011-09-21
Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com
Supported by:
Project supported by the the National Natural Science Foundation of China (No. 20772035), the Natural Science of Foundation of Guangdong Provine (No. 5300082) and the 3rd Talents Special Funds of Guangdong Higher Education (No. [2011]431).

文章分享

摘要/Abstract

在氟化钾作催化剂和四氢呋喃作溶剂的条件下, 研究了系列脂肪胺亲核试剂与5-烷氧基-3,4-二卤-2(5H)-呋喃酮发生的反应, 通过旋光度, UV-Vis, IR, ¹H NMR, ¹³C NMR, MS, 元素分析和X 射线单晶衍射等表征方法对产物进行结构表征, 发现通常情况下发生预期的串联迈克尔加成-消除反应, 合成了13 个新的β-胺基-2(5H)-呋喃酮. 但是, 空间位阻较大的二环己基胺与5-烷氧基-3,4-二卤-2(5H)-呋喃酮反应时, 却得到了4 个异常的2(5H)-呋喃酮开环产物, 其可能是经开环重排反应的机理得到的.

关键词: 5-烷氧基-3,4-二卤-2(5H)-呋喃酮, 脂肪族仲胺, 串联迈克尔加成-消除反应, β-胺基-2(5H)-呋喃酮, 开环重排反应

Using KF as catalyst and tetrahydrofuran as solvent, 5-alkyloxy-3,4-dihalo-2(5H)-furanones was reacted with several aliphatic amines. The chemical structures and absolute configurations of the products were confirmed via rotation, UV-Vis, IR, ¹H NMR, ¹³C NMR, MS techniques, elemental analysis and X-ray single crystal diffraction. Thirteen new normal products β-amino-2(5H)-furanones were obtained via the tandem Michael addition-elimination reaction as anticipated in most cases. However, the reaction between the larger steric dicyclohexyl amine and 5-alkyloxy-3,4-dihalo-2(5H)-furanones yielded four new abnormal products, (E)-alkyl 2-halo-4-dicyclohexylamino-4-oxobut-2-enoate. The possible mechanism for the formation of 2(5H)-furanone ring-opening products involving in the rearrangement reaction was proposed.

Key words: 5-alkoxy-3,4-dihalo-2(5H)-furanone, aliphatic saturated secondary amine, tandem Michael addition-elinmination reaction, β-amino-2(5H)-furanone, ring-opening rearrangement reaction

引用此文

傅建花, 汪朝阳, 霍景沛, 谭越河, 曾荣华. 5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究[J]. 有机化学, 2012, 32(01): 104-112.

Fu Jianhua, Wang Zhaoyang, Huo Jingpei, Tan Yuehe, Zeng Ronghua . Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines[J]. Chin. J. Org. Chem., 2012, 32(01): 104-112.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Juan, H. V. E.; Saad, J. R.; Giordano, O. S.; Garcia, C.; Martin, T.; Martin, V. S.; Sosa, M. E.; Tonn, C. E. J. Nat. Prod. 2008, 71, 190.

[2] Wei, M.-X.; Feng, L.; Li, X.-Q.; Zhou, X.-Z.; Shao, Z.-H. Eur. J. Med. Chem. 2009, 44, 3340.

[3] Pimentel-Elardo, S. M.; Kozytska, S.; Bugni, T. S.; Ireland, C. M.; Moll, H.; Hentschel, U. Mar. Drugs 2010, 8, 373.

[4] Prasad, K. R.; Gandi, V. R. Tetrahedron: Asymmetry 2010, 21, 275.

[5] Lattmann, E.; Billington, D. C.; Langley, C. A. Drug Des. Discovery. 1999, 16, 243.

[6] Arayarat, P.; Singh, H.; Lattmann, E. Sci. Asia 2001, 27, 121.

[7] Lattmann, E.; Dunn, S.; Niamsanit, S.; Sattayasai, N. Bioorg. Med. Chem. Lett. 2005, 15, 919.

[8] Lattmann, E.; Sattayasai, N.; Schwalbe, C. S.; Niamsanit, S.; Billington, D. C.; Lattmann, P.; Langley, C. A.; Singh. H.; Dunn, S. Curr. Drug Discovery Technol. 2006, 3, 125.

[9] Tanoury, G. J.; Chen, M.; Dong, Y.; Forslund, R. E.; Magdziak, D. Org. Lett. 2008, 10, 185.

[10] Yu, Z.-L.; Hu, S.-Q.; Li, S.-L.; Fu, Y-Q. Chin. J. Org. Chem. 2008, 28, 1119 (in Chinese). (郁兆莲, 胡少强, 李森兰, 傅玉琴, 有机化学, 2008, 28, 1119.)

[11] Song, X.-M.; Wang, Z.-Y.; Li, J.-X.; Fu, J.-H. Chin. J. Org. Chem. 2009, 29, 1804 (in Chinese). (宋秀美, 汪朝阳, 李建晓, 傅建花, 有机化学, 2009, 29, 1804.)

[12] Mo, Y.-Q.; Wang, Z.-Y.; Li, J.-X.; Hong, W.-K. Chin. J. Org. Chem. 2010, 30, 1051 (in Chinese). (莫阳青, 汪朝阳, 李建晓, 洪文坤, 有机化学, 2010, 30, 1051.)

[13] Song, X.-M.; Tan, Y.-H.; Li, J.-X.; Wang, Z.-Y. Chin. J. Org. Chem. 2010, 30, 1890 (in Chinese). (宋秀美, 谭越河, 李建晓, 汪朝阳, 有机化学, 2010, 30, 1890.)

[14] Lattmann, E.; Lattmann, P.; Singh, H. WO 2004106315, 2004[Chem. Abstr. 2005, 142, 38133].

[15] Chen, Q.-H.; Geng, Z.; Huang, B. Tetrahedron: Asymmetry 1995, 6, 401.

[16] Kurbangalieva, A. R.; Devyatova, N. F.; Bogdanov, A. V.; Berdnikov, E. A.; Mannafov, T. G.; Krivolapov, D. B.; Litvinov, I. A.; Chmutova, G. A. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 607.

[17] Devyatova, N. F.; Kosolapova, L. S.; Kurbangalieva, A. R.;Berdnikov, E. A.; Lodochnikova, O. A.; Litvinov, I. A.; Chmutova, G. A. Russ. J. Org. Chem. 2008, 44, 1225.

[18] Kurbangalieva, A. R.; Devyatova, N. F.; Kosolapova, L. S.; Lodochnikova, O. A.; Berdnikov, E. A.; Litvinov, I. A.; Chmutova, G. A. Russ. Chem. Bull. 2009, 58, 126.

[19] Polezhaeva, N. A.; Volodina, Yu. M.; Kalinina, I. V.; Sakhibullina, V. G.; Chmutova, G. A.; Galkin, V. I.; Cherkasov, R. A. Russ. J. Gen. Chem. 2002, 72, 1202.

[20] Kurbangalieva, A. R.; Bogdanov, A. V.; Movchan, A. I.; Chmutova, G. A. Russ. J. Org. Chem. 2004, 40, 1216.

[21] Teitei, T. Aust. J. Chem. 1986, 39, 503.

[22] Mellor, J. M.; Wagland, A. M. J. Chem. Soc., Perkin Trans. 1 1989, 997.

[23] Dawson, J. R.; Mellor, J. M. Tetrahedron Lett. 1995, 36, 9043.

[24] Beccalli, E. M.; Marchesini, A. Tetrahedron 1995, 51, 2353.

[25] Hashmi, A. S. K.; Grundl, M. A.; Nass, A. R.; Naumann, F.; Bats, J. W.; Bolte, M. Eur. J. Org. Chem. 2001, 4705.

[26] Iyer, V. K.; Horwitz, J. P. J. Org. Chem. 1982, 47, 644.

[27] Morlender-Vais, N.; Mandelbaum. A. J. Mass Spectrom. 1999, 34, 637.

[28] Xu, Y.; Zhu, S. Z. Tetrahedron 2001, 57, 3909.

[29] Abe, M.; Hattori, M.; Takegami, A.; Masuyama, A.; Hayashi, T.; Seki, S.; Tagawa, S. J. Am. Chem. Soc. 2006, 128, 8008.

[30] Briehl, H.; Lukosch, A.; Wentrup C. J. Org. Chem. 1984, 49, 2772.

[31] Rickborn, B. Org. React. 1998, 52.

[32] Bibas, H.; Moloney, D. W. J.; Neumann, R.; Shtaiwi, M.; Bernhardt, P. V.; Wentrup, C. J. Org. Chem. 2002, 67, 2619.

[33] Chiang, Y.; Gaplovsky, M.; Kresge, A. J.; Leung, K. H.; Ley, C.; Mac, M.; Persy, G.; Phillips, D. L.; Popik, V. V.; Roedig, C.; Wirz, J.; Zhu, Y. J. Am. Chem. Soc. 2003, 125, 12872.

[34] Finnerty J. J.; Wentrup C. J. Org. Chem. 2004, 69, 1909.

[35] Halton, B.; Dixon, G. M.; Jones, C. S.; Parkin, C. T.; Veedu, R. N.; Bornemann, H.; Wentrup, C. Org. Lett. 2005, 7, 949.

[36] Veedu, R. N.; Kokas, O. J.; Couturier-Tamburelli, I.; Koch, R.; Aycard, J.-P.; Borget, F.; Wentrup, C. J. Phys. Chem. A 2008, 112, 9742.

[37] Fulloon, B. E.; Wentrup, C. Aust. J. Chem. 2009, 62, 115.

[38] Alvarez, M. A.; García, M. E.; Martínez, M. E.; Menéndez, S.; Ruiz, M. A. Organometallics 2010, 29, 710.

5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究

Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines

PDF

可视化

被引次数

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 4

编辑推荐

相关统计

本文评价

[1]	叶斌, 莫广珍, 关丽涛, 吴彦城, 陈任宏, 汪朝阳. 3-卤-4-脂肪胺基-5-联苯氧基-2(5H)-呋喃酮的合成[J]. 有机化学, 2015, 35(11): 2420-2428.
[2]	陈任宏, 傅建花, 李国良, 谭越河, 汪朝阳, 袁萍. 5-烷氧基-3,4-二卤-2(5H)-呋喃酮与不饱和胺的反应研究[J]. 有机化学, 2012, 32(01): 95-103.
[3]	谭越河, 汪朝阳, 郝志峰, 李建晓. (5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮与氨基酸的串联反应[J]. 有机化学, 2011, 31(08): 1222-1229.
[4]	宋秀美, 谭越河, 李建晓, 汪朝阳. 无保护α-氨基酸合成多手性中心2(5H)-呋喃酮化合物[J]. 有机化学, 2010, 30(12): 1890-1897.