Convenient synthesis of β-allenic α-difluoromethylenephosphonic acid monoesters:Potential synthons for cyclic phosphate mimics
Convenient synthesis of β-allenic α-difluoromethylenephosphonic acid monoesters:Potential synthons for cyclic phosphate mimics
摘要
β-Allenic α-difluoromethylenephosphonic acid monoesters were prepared under mild conditions for the first time by hydrolyzing the corresponding diethyl phosphonates in aqueous sodium hydroxide solution.
β-Allenic α-difluoromethylenephosphonic acid monoesters were prepared under mild conditions for the first time by hydrolyzing the corresponding diethyl phosphonates in aqueous sodium hydroxide solution.
基金
We thank the National Natural Science Foundation of China for financial support(No.20572124).
参考文献7
-
1[1](a) J.Nieschalk,A.S.Batsanov,D.O'Hagan,et al.Tetrahedron 52 (1996) 165;(b) R.D.Chambers,D.O'Hagan,R.B.Lamont,et al.J.Chem.Soc.,Chem.Commun.(1990) 1053;(c) R.D.Chambers,R.Jaouhari,D.O'Hagan,Tetrahedron 45 (1989) 5101;(d) G.M.Blackburn,D.Brown,S.J.Martin,et al.J.Chem.Soc.,Perkin Trans.1 (1987) 181;(e) G.M.Blackburn,D.E.Kent,J.Chem.Soc.,Perkin Trans.1 (1986) 913;(f) G.M.Blackburn,D.Brown,S.J.Martin,J.Chem.Res.,Synop.(1985) 92;(g) G.M.Blackburn,D.A.England,F.J.Kolkman,J.Chem.Soc.,Chem.Commun.17 (1981) 930. 被引量：1
-
2[2](a) A.M.Kawamoto,M.M.Campbell,J.Chem.Soc.,Perkin Trans.1 8 (1997) 1249;(b) N.A.Caplan,C.I.Pogson,D.J.Hayes,et al.J.Chem.Soc.,Perkin Trans.1 3 (2000) 421;(c) T.Yokomatsu,Y.Hayakawa,T.Kihara,et al.Bioorg.Med.Chem.8 (2000) 2571;(d) Y.Xu,G.D.Prestwich,Org.Lett.4 (2002) 4021;(e) G.Hum,J.Lee,S.D.Taylor,Bioorg.Med.Chem.Lett.12 (2002) 3471;(f) E.Pfund,T.Lequeux,S.Masson,M.Vazeux,Org.Lett.4 (2002) 843;(g) T.Yokomatsu,J.Kato,C.Sakuma,S.Shibuya,Synlett (2003) 1407;(h) T.Murano,Y.Yuasa,H.Kobayakawa,et al.Tetrahedron 59 (2003) 10223;(i) X.F.Li,A.Bhandari,C.P.Holmes,A.K.Szardenings,Bioorg.Med.14 (2004) 4301;(j) A.Gautier,G.Garipova,C.Salcedo,et al.Angew.Chem.Int.Ed.43 (2004) 5963. 被引量：1
-
3[3](a) M.Frederickson,R.Grigg,Org.Prep.Proced.Int.29 (1997) 33;(b) R.Zimmer,C.U.Dinesh,E.Nandanan,F.A.Khan,Chem.Rev.100 (2000) 3067;(c) S.Ma,Chem.Rev.105 (2000) 2829. 被引量：1
-
4[4]T.Y.Okomatsu,A.Ichimura,J.Kato,S.Shibuya,Synlett (2001) 287. 被引量：1
-
5[5]E.R.H.Jones,G.H.Whitham,M.C.Whiting,J.Chem.Soc.(1954) 3201. 被引量：1
-
6[6]A.E.Feiring,M.C.Hovey,S.D.Arthur,J.Fluorine Chem.24 (1984) 125. 被引量：1
-
7[7]Typical procedure for the synthesis of 2a.To a mixture of 1a (1.27 g,5 mmol),EtOH (5 mL) and water (10 mL) was added 1 mol/L NaOH solution (10 mL) slowly.The mixture was stirred at room temperature for about 0.5 h to the completion of the reaction (monitored by TLC).Then the reaction mixture was diluted with water (15 mL),acidified with 10% HCl to pH 2-3 and extracted with EtOAc (20 mL (3).The organic layer was washed with saturated NaCl solution and dried over anhydrous Na2SO4.After removal of solvent in vacuo,2a (1.05 g,93% yield) was obtained as an oil without further purification.IR (film):2250,1979,1640,1233,1033 cm (1; 1H-NMR (CDCl3,300 MHz) δppm:10.4 (s,1H),5.30-5.23 (m,1 H),4.27-4.18 (m,2 H),1.75 (s,6 H),1.35 (t,3 H,J = 7.2 Hz); 13C-NMR (CDCl3,125 MHz) δppm:204.3-204.0 (m),116.7 (td,JC-F = 247.1 Hz,JC-P = 189.1 Hz),102.3,84.9 (td,JC-F = 26.7 Hz,JC-P = 15.9 Hz),64.8 (d,JC-P = 6.6 Hz),19.4,16.2; 19F-NMR (CDCl3,282 MHz) δppm:(106.9 (dd,JP-F = 117.0 Hz,JH-F = 10.1 Hz); 13P-NMR (CDCl3,121 MHz) δppm:6.97 (t,JP-F = 117.0 Hz); EIMS m/z (%):227(M+ + 1,21.16),206(43.86),134(59.72),119(73.56),117(43.58),97(100.00),96(44.83),77(88.85),65(58.65).HRMS (MALDI):calcd.for C8H13F2O3PNa(M+ + Na):249.0471,found:249.0462. 被引量：1
-
1陈俊华,赵东兵,张孝琴,罗美明.六齿咪唑鎓盐的合成[J].化学研究与应用,2006,18(4):413-414.
-
2娄本勇,林棋.Synthesis and Crystal Structure of a Ca~Ⅱ Coordination Polymer of H_2Adefovir (H_2Adefovir={[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl}phosphonic Acid)[J].Chinese Journal of Structural Chemistry,2011,30(7):1059-1063.
-
3Hong Wu HE,Jun Wang,Zhao Jie LIU (Institute of Organic Synthesis, Central China Normal University, Wuhan 430070).SYNTHESIS OF α-(SUBSTITUTED PHENOXY ACETOXY) ALKYL PHOSPHONATES[J].Chinese Chemical Letters,1994,5(1):35-38. 被引量：1
-
4Jun WANG,Hong Wu HE and Zhao Jie LIU(Institute of Organic Synthesis, Central China Normal University, Wuhan, 430070)(Department of Chemistry, Xiaogan Teachers College, Hubei, 432100).Synthesis of α-[2-(2, 4-Dichlorophenoxy) Propionyloxy] Alkyl Phosphonates[J].Chinese Chemical Letters,1997,8(11):943-944.
-
5SU Feng yu,LI Yan,TANG Jun,TIAN Yan qing,ZHAO Ying ying,ZHOU En le.Synthesis and Investigation of Monoesters of Polymaleic Acids with Azo-Group[J].Chemical Research in Chinese Universities,1997,13(4):70-74.
-
6赵玉春,姚林山,李建月,于颖慧,侯广峰,高金胜.Two Cobalt(Ⅱ)Coordination Polymers Based on Tetrazylphosphonate and Tetrazylphosphonic Acid Ligands[J].Chinese Journal of Structural Chemistry,2017,36(3):453-462. 被引量：1
-
7Zhou, J,Chen, RY.Synthesis and Stereochemistry of New Cyclic Phosphate-phosphonates[J].Chinese Chemical Letters,1997,8(1):11-12.
-
8ZHOU Jia CHEN Ru Yu (Institute of Elemento Organic Chemistry, State Key Laboratory of Elemento Organic Chemistry, Nankai University, Tianjin, 300071) WANG Hong Gen (Central Laboratory, Nankai University, Tianjin, 300071).Crystal Structure of cis-2-〔(P,P-Diethoxy)phosphono(m-nitro)benzyloxy〕-4-Phenyl-5,5-Dimethyl-1,3,2-Dioxaphosphorinane 2-Sulfide[J].Chinese Journal of Structural Chemistry,1999,18(2):23-27.
-
9陆军,孟淑兰,李德谦,叶伟贞.Rare Earth Separation with 1-Hexyl-4-Ethyloctyl Isopropylphosphonic Acid Extractant[J].Journal of Rare Earths,2000,18(4):258-261. 被引量：3
-
10周春辉,周杰,胡振原,金矿,胡劲松.Three New Coordination Polymers Constructed by Adjusting the Angles of Pyridyl or Imidazolyl-based Synthons： Structures and Solid UV-vis Properties[J].Chinese Journal of Structural Chemistry,2016,35(8):1245-1252.
