中文 |
English |
Email Alert
烯氯化合物及其合成进展
Advances in the Synthesis of Vinyl Chloride Compounds
烯氯常见于天然产物中,并被认为是其生物活性官能团之一,在功能材料方面也多有应用,同时也是有机合成中一类重要的合成子。因而,烯氯的制备方法一直是有机合成化学和制药化学的热点研究内容之一。近年来,制备烯氯的新方法和新试剂不断出现,本文基于不同的反应类型, 对烯氯的构筑方法进行了综述,并列举了海洋天然产物malyngamides全合成中烯氯应用的重要性。
Vinyl chloride is an important functional group in many biologically and pharmaceutically active compounds, some vinyl chloride derivatives have been employed as organic materials, including polymers, and also are employed as the building block in organic synthesis. The construction of vinyl chloride is widely studied, new method and reagent are continuing to emerge in recently years. In this paper, the recent progress in the synthesis of vinyl chloride is reviewed according to the different reaction types, and its application in the total synthesis of marine natural product malyngamides is covered.
Contents
1 Introduction
2 Synthesis of vinyl chloride by Wittig reaction
3 Cr,Pd,Ti,In,Mg,and Cu-mediated reaction to synthesize vinyl chloride
3.1 Organic Cr-mediated reaction
3.2 Pd-mediated reaction
3.3 Ti-mediated reaction
3.4 In-mediated reaction
3.5 MgCl2-mediated reaction
3.6 Cu-mediated reaction
4 Using other methods to synthesize vinyl chloride
5 Studied on the synthesis of vinyl chloride and applied in marine natural product malyngamides
5.1 Synthesis of vinyl chloride by Wittig reaction in malyngamides M, O, P, Q, R
5.2 Synthesis of vinyl chloride by the reaction of n-Bu4NI with 1,2-dichloroethane in malyngamides K, L, 5-epi-C
6 Conclusion
有机合成
organic synthesis
[1] Kahnberg P, Sterner O. Tetrahedron, 2001, 57: 7181—7184
[2] Kahnberg P, Lee C W, Grubbs R H, Sterner O. Tetrahedron, 2002, 58: 5203—5208
[3] Graf K M, Tabor M G, Brown M L, Paige M. Org. Lett., 2009, 11: 5382—5385
[4] Smith A B, Razler T M, Meis R M, Pettit G R. J. Org. Chem., 2008, 73: 1201—1208
[5] Choi Y, Li L, Grill S, Gullen E, Lee C S, Gumina, G, Tsujii E, Cheng Y C, Chu C K. J. Med. Chem., 2000, 43: 5238—5246
[6] Gallimore W A, Scheuer P J. J. Nat. Prod., 2000, 63: 1422—1424
[7] Milligan K E, Márquez B, Williamson R T, Davies-Coleman M, Gerwick W H. J. Nat. Prod., 2000, 63: 965—968
[8] Gaynor S T. Macromolecular, 2012, 45: 2200—2208
[9] Li G, Wang H, Zheng H, Bai R. Journal of Polymer Science Part A: Polymer Chemistry, 2010, 48: 1348—1356
[10] Whipp C J, Turiso F G L. Tetrahedron Lett., 2008, 49: 5508—5510
[11] Esmieu W R, Worden S M, Catterick D, Wilson C, Hayes C J. J. Org. Lett., 2008, 10: 3045—3048
[12] Kao H L, Lee C F. Org. Lett., 2011, 13: 5204—5207
[13] Hu T, Shen M, Chen Q, Li C. Org. Lett., 2006, 8: 2647—2650
[14] Blackburn L, Pei C, Taylor R J K. Synlett, 2002, 215—218
[15] Shuto S, Niizuma S, Matsuda A. J. Org. Chem., 1998, 63: 4489—4493
[16] Barrett A G M, Hamprecht D, Ohkubo M. J. Org. Chem., 1997, 62: 9376—9378
[17] MacCoss R N, Balskus E P, Ley S V. Tetrahedron Lett., 2003, 44: 7779—7781
[18] Takai K, Kurcda T, Nakatsukasa S, Oshima K, Nozaki H. Tetrahedron Lett., 1985, 26: 5585—5588
[19] Takai K, Nitta K, Utimoto K. J. Am. Chem. Soc., 1986, 108: 7408—7410
[20] Takai K, Kokumai R, Nobunaka T. Chem. Commun., 2001, 1128—1129
[21] Concellón J M, Rodríguez-Solla H, Méjica C. Tetrahedron Lett., 2004, 45: 2977—2979
[22] Concellón J M, Bernad P L, Méjica C. Tetrahedron Lett., 2006, 46: 569—571
[23] Bckvall J E, Nilsson Y I M, Andersson P G, Gatti R G P, Wu J. Tetrahedron Lett., 1994, 35: 5713—5716
[24] Nilsson Y I M, Gatti R G P, Andersson P G, Bckvall J E. Tetrahedron, 1996, 52: 7511—7523
[25] Holzapfel C W, Marais L. Tetrahedron Lett., 1998, 39: 2179—2182
[26] Jiang H, Ma S, Zhu G, Lu X. Tetrahedron, 1996, 52: 10945—10954
[27] Keck D, Vanderheiden S, Brse S. Eur. J. Org. Chem., 2006, 4916—4923
[28] Steinhagen H, Corey E J. Org. Lett., 1999, 1: 823—824
[29] Métay E, Hu Q, Negishi E I. Org. Lett., 2006, 8: 5773—5776
[30] Kim S, Kim S, Lee T, Ko H, Kim D. Org. Lett., 2004, 6: 3601—3604
[31] Takeda T, Sasaki R, Fujiwara T. J. Org. Chem., 1998, 63: 7286—7288
[32] Takeda T, Endo Y, Reddy A C S, Sasak R, Fujiwara T. Tetrahedron, 1999, 55: 2475—2486
[33] Takeda T, Nozaki N, Fujiwara T. Tetrahedron Lett., 1998, 39: 3533—3536
[34] Wei H X, Gao J J, Li G. Tetrahedron Lett., 2001, 42: 9119—9122
[35] Tsai C C, Chien C C, Chang Y C, Lin H C, Yan T H. J. Org. Chem., 2005, 70: 5745—5747
[36] Cook G R, Hayashi R. Org. Lett., 2006, 8: 1045—1048
[37] Tsuji H, Fujimoto T, Endo K, Nakamura M, Nakamura E. Org. Lett., 2008, 10: 1219—1221
[38] Wang Y, Lam H W. J. Org. Chem., 2009, 74: 1353—1355
[39] Ma S, Zhang J, Cai Y, Lu L. J. Am. Chem. Soc., 2003, 125: 13954—13955
[40] Bejot R, Tisserand S, Reddy L M, Barma D K, Baati R, Falck J R, Mioskowski C. Angew. Chem. Int. Ed., 2005, 44: 2008—2011
[41] Baati R, Barma D, Krishna U M, Mioskowski C, Falck J R. Tetrahedron Lett., 2002, 43: 959—961
[42] Baati R, Barma D K, Falck J R, Mioskowski C. J. Am. Chem. Soc., 2001, 123: 9196—9197
[43] Ram R N, Meher N K. Org. Lett., 2003, 5: 145—147
[44] Ram R N, Manoj T P. Org. Lett., 2008, 10: 2243—2246
[45] Barluenga J, Baragaa B, Concellón J M. J. Org. Chem., 1999, 64: 2843—2846
[46] Kataoka T, Kinoshita H, Kinoshika S, Iwamura T, Watanabe S. Angew. Chem. Int. Ed., 2000, 39: 2358—2360
[47] Moreno-Dorado F J, Guerra F M, Manzano F L, Aladro F J, Jorge Z D, Massanet G M. Tetrahedron Lett., 2003, 44: 6691—6693
[48] Lebrun M E, Marquand P L, Berthelette C. J. Org. Chem., 2006, 71: 2009—2013
[49] Lemay A B, Vulic K S, Ogilvie W W. J. Org. Chem., 2006, 71: 3615—3618
[50] Banwell M G, Phillis A T, Willis A C. Org. Lett., 2006, 8: 5341—5344
[51] Chen J, Shi Z F, Zhou L, Xie A L, Cao X P. Tetrahedron Lett., 2010, 66: 3499—3507
[52] Chen J, Fu X G, Zhou L, Zhang J T, Qi X L. J. Org. Chem., 2009, 74: 4149—4157
[53] Zhang J T, Qi X L, Chen J, Li B S, Zhou Y B. J. Org. Chem., 2011, 76: 3946—3959
/
| 〈 |
|
〉 |
PDF
(1441KB)
