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1-烷氧基-3-芳氧基-2-丙醇和1,3-二芳氧基-2-丙醇的合成 被引量:3

Synthesis of 1-Alkoxy-3-aroxy-2-propanol and 1,3-Diaroxy-2-propanol
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摘要 以 3 芳氧基 1,2 环氧丙烷与伯醇、仲醇及酚为原料 ,通过碱催化开环反应 ,区域选择性地合成 1 烷氧基 3 芳氧基 2 丙醇以及 1,3 二芳氧基 2 丙醇化合物 ,收率为 790 %~ 98% . Alkoxy 3 aroxy 2 propanol and 1,3 diaroxy 2 propanol compounds were synthesized regioselectively by base catalyzed opening reactions of 3 aroxy 1,2 epoxides with alcohol and phenol in 79~98% yields.
出处 《山东大学学报(理学版)》 CAS CSCD 北大核心 2003年第4期96-99,共4页 Journal of Shandong University(Natural Science)
基金 山东省自然科学基金资助项目 (Z2 0 0 2D0 5 ) 山东大学交叉学科预研项目基金资助项目
关键词 3-芳氧基-1 2-环氧丙烷 碱催化开环反应 1-烷氧基-3-芳氧基-2-丙醇 1 3-二芳氧基-2-丙醇 aroxy 1,2 epoxides base catalyzed opening reaction 1 Alkoxy 3 aroxy 2 propanol 1,3 diaroxy 2 propanol
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参考文献11

  • 1谭伟,沙磊,赵宝祥.环氧烷化合物在有机合成中的应用[J].合成化学,2003,11(5):384-390. 被引量:6
  • 2李祖义 金浩 石俊.Biosynthesis of Chiral Epoxides .有机化学,2001,21:247-251.
  • 3赵宝祥,王大威,左华,钱广桃,苗俊英.1-烷(苯)氧基-3-(3,4-亚甲基二氧)苯基-2-丙醇的合成与生物活性研究[J].有机化学,2003,23(9):1026-1028. 被引量:7
  • 4Taylor S K. Reaction of Epoxides with Ester, Ketone and Amide Enolates [J]. Tetrahedron, 2000, 56:1149 - 1163.
  • 5Smith J G. Synthetically useful reactions of epoxides [J]. Synthesis , 1984, 229 - 656.
  • 6Olah G A, Fang A P, Meider D. Synthetic methods and reactions; 68. Nafion-H-catalyzed hydration and methanolysis of epoxides [J]. Synthesis, 1981, 280- 281.
  • 7Posner G H, Rogers D Z, Kinzig C M, Gurria G M. Organic reactions at alumina surfaces. Displacement reactions effected by alcohols, thiols, and acetic acid on dehydrated alumina[J]. Tetrahedron Lett, 1975, 16:3597 - 3600.
  • 8Otera J, Yoshinaga Y, Hirakawa K, Nakata T. Highly regioselective ring opening of epoxides with alcohols catalyzed by organotin phosphate condensates [J]. Tetrahedron Lett, 1985, 26:3219 - 3222.
  • 9Iranpoor N, Baltork I M. 2,3-Dichloro-5, 6-Dicyano-p-Benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxides [ J ]. Tetrahedron Lett,1990, 31 : 735 - 738.
  • 10Zhao B-X, Du A-Y, Miao J-Y, et al. Effects of novel safrole oxide derivatives, 1-methoxy-3- (3,4-methylenedioxyphenyl)-2-propanol and 1-ethoxy-3-( 3, 4-methylenedioxyphenyl )-2-propanol, on apoptosis induced by deprivation of survial factors in vascular endothelial cells[ J]. General Pharmacology,2003 (in press).

二级参考文献23

  • 1Bakalarz-Jezioma A, Helinski J, Krawiecka B J. Synthesis of Multifunctionalized Phosphonic Acid Esters via Opening of Oxiranes and Azetidinium Salts with Phosphoryl-substituted Carbanions [ J ]. Org Soc Perkin Trans ,2001,1:1086 - 1090.
  • 2Gathergood N, Zhuang W, Jφrgensen K A. Catalytic Enantioseleetive Friedel-Crafts Reactions of Aromatic Compounds with Glyoxylate: A Simple Procedure for the Synthesis of Optically Active Aromatic Mandelic Acid Esters [ J ]. J Am Chem Soc , 2000, 122 :12257 - 12522.
  • 3Bandini M, Cozzi P G, Melehiorre P, et al. In Br3-Catalyzed Friedel-Crafts Addition of Indoles to Chiral Aromatic Epoxides: A Faeih Route to Enantiopure Indolyl Derivatives [ J ]. J Org Chem , 2002, 67 :5386 - 5389.
  • 4Loefstedt J, Pettersson-Fasth H, Baeckvall J. Stereroselective Route towards 2, 5-Disubstituted Piperidine Alkaloids. Synthesis of ( + )-Pseudoconhydrine and ( + ) -epi-Pseudoconhydrin [ J ]. Tetrahedron, 2000,56:2225 - 2230.
  • 5Anson C E, Dave G, Stephenson G R. Srereocontrolled Preparation of Stereocomplementary Regioisomerie Triearbonyliron Complexes in Enantiopure Form[ J]. Tetrahedron ,2000,56:2273 - 2281.
  • 6Subburaj K, Okamoto S,Sato F. Development of New Chiral Building Blocks for Synthesis of Bicyclo [ 3.3.0] octane[ J]. J Org Chem ,2002,67 : 1024 - 1026.
  • 7Younes M R, Chaabouni M M, Baklouti A. Dimercaptoethane Oxirane Ring Opening Reaction: ??? ′-Dihydroxy Dithioether Synthesis [ J ]. Tetrahedron Letters ,2001,42:3167 - 3169.
  • 8Mordini A, Bindi S, Capperueei A, et al. Stereoselective Access to Hydroxy Oxetanes and Tetrahydrooxepines through Isomerization of Oxiranyl Ethers [ J ].J Org Chem ,2001,66:3201 -3205.
  • 9Righi G, Bovieelli Paolo, Sperandio A. An Easy Deoxygenation of Conjugated Epoxides [ J ]. Tetrahedron,2000,56 : 1733 - 1737.
  • 10Sehaus S E,Brandes B D,Larrow J F, et al. Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (Salen) Co( Ⅲ ) Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols [ J ]. J Am Chem Soc ,2002,124(7) :1307 - 1315.

共引文献10

同被引文献37

  • 1沙磊,赵宝祥,谭伟,苗俊英.细胞凋亡诱导剂研究进展[J].有机化学,2004,24(8):864-871. 被引量:4
  • 2李洁.选择性杀虫剂蚊蝇醚[J].农药,1994,33(6):30-31. 被引量:13
  • 3Collet M,Baltas M,Martinez A,et al. Addition of lithium ethyl fluoroacetate to cis and trans α,β-epoxyaldehydes. Access to C2 fluorinated butyrolactones[J].Tetrahedron Lett,2003,44(9):1891-1894.
  • 4Kim K,Okamoto S,Takayama Y,et al. Asymmetric synthesis of stereodefined α-alkyl-γ-benzyloxymethyl-β-trimethylsilyl-γ-butyrolactones that serve as an efficient precursor for constructing carbon skeletons having a tertiary or quaternary stereogenic center[J].Tetrahedron Lett,2002,43(23):4237-4239.
  • 5Maslak V,Matovic R,Saiic R N. Titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides: a new method for the synthesis of γ-butanolides[J].Tetrahedron Lett,2002,43(31):5411-5413.
  • 6Santos M R L,Barreiro E,Braz-Filho R,et al. Synthesis of functionalized γ-spirolactone and 2-oxabicyclo[3.3.0]octane derivatives from nucleophilic oxirane ring opening[J].Tetrahedron,2000,56(30):5289-5295.
  • 7Sanière M,Charvet I,Merrer Y L,et al. Enantiopure hydroxylactones from L-ascorbic and D-isoascorbic acids. Part I. Synthesis of (-)-muricatacin[J].Tetrahedron,1994,51(6):1653-1662.
  • 8Zhao B X,Du A Y,Miao J Y,et al. Effects of novel safrole oxide derivatives,1-methoxy-3-(3,4-methylenedioxyphenyl)-2-propanol and 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol,on apoptosis induced by deprivation of survival factors in vascular endothelial cells[J].Vasc Pharmacol,2003,40(3):183-187.
  • 9DePuy C H,Breitbeil F W,Eilers K L. The reaction of diethyl malonate with styrene oxide[J].J Org Chem,1964,29(9):2810-2810.
  • 10Hanessian S,Abad-Grillo T,McNaughton-Smith G. Synthesis of (4S)-hydroxymethyl-(2R)-(2-propyl)-butyrolactone: A quest for a practical route to an important hydroxyethylene isostere chiron[J].Tetrahedron,1997,53(18):6281-6294.

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