期刊文献+

新型α-乙氧羰基-γ-芳氧甲基-γ-丁内酯的合成

Synthesis of Novel α-Ethoxycarbonyl-γ-aroxymethyl-γ-butyrolactone Derivatives
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摘要 3-芳氧基-1,2-环氧丙烷与丙二酸二乙酯在乙醇钠存在下反应,合成了6个新型α-乙氧羰基-γ-芳氧甲基-γ-丁内酯,收率47%~89%.其结构经1H NMR, IR和MS表征. A series of novel α-ethoxycarbonyl-γ-aroxymethyl-γ-butyrolactone derivatives were synthesized in 47%~89% yields by ring opening-cyclization of 2-(aroxymethyl)oxirane derivatives with diethyl malonate and the structures were confirmed by ~1H NMR, IR and MS.
出处 《合成化学》 CAS CSCD 2005年第4期344-348,共5页 Chinese Journal of Synthetic Chemistry
基金 山东省自然科学基金资助项目(Z2002D05) 教育部重点资助项目
关键词 区域选择性 环氧丙烷 丙二酸二乙酯 Γ-丁内酯 立体异构体 合成 regioselectivity epoxy diethyl malonate γ-butyrolactone stereoisomer synthesis
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参考文献35

  • 1Kupchan S M,Dessertine A L,Blaylock B T,et al.Isolation and structural elucidation of allamandin and antileukemic iridoid lactone from allamanda cathartica[J] J Org Chem,1974,39(17):2477-2482.
  • 2Trost B M,Balkovec J M,Mao M K-T. A biomimetic approach to plumericin[J].J Am Chem Soc,1983,105(22):6755-6757.
  • 3Pour M,pulák M,Buchta V,et al. 3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones: Synthesis and biological activity of a novel group of potential antifungal drug[J].J Med Chem,2001,44(17):2701-2706.
  • 4Peterson E M,Xu K,Holland K D,et al. α-Spirocyclopentyl- and α-spirocyclopropyl-y-butyrolactones: Conformationally constrained derivatives of anticonvulsant and convulsant α,α-disubstituted γ-butyrolactones[J].J Med Chem,1994,37(2):275-286.
  • 5González A G,Silva M H,Padrón J I,et al. Synthesis and antiproliferative activity of a new compound containing an α-methylene-γ-lactone group[J].J Med Chem,2002,45(12):2358-2361.
  • 6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
  • 7Samarat A,Amri H,Landais Y. Enantioselective synthesis of functionalized γ-butyrolactones[J].Tetrahedron,2004,60(40):8949-8956.
  • 8Wayne M G,Smithers M J,Rayner J W,et al. Heterocyclic compounds as platelet aggregation inhibitors[P].WO 9 422 835,1994.
  • 9Wayne M G,Smithers M J,Rayner J W,et al. Heterocyclic derivatives as platelet aggregation inhibitors[P].WO 9 422 834,1995.
  • 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.

二级参考文献23

  • 1李祖义 金浩 石俊.Biosynthesis of Chiral Epoxides .有机化学,2001,21:247-251.
  • 2Otera 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.
  • 3Iranpoor 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.
  • 4Zhao 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).
  • 5Piantadosi C, Hall I H, Wyrick S D, Ishaq K S. Hypocholesterolemic activity of 1,3-bis (substituted phenoxy)-2-propanones [ J ]. J Med Chem, 1976, 19(2) : 222 - 229.
  • 6Taylor S K. Reaction of Epoxides with Ester, Ketone and Amide Enolates [J]. Tetrahedron, 2000, 56:1149 - 1163.
  • 7Smith J G. Synthetically useful reactions of epoxides [J]. Synthesis , 1984, 229 - 656.
  • 8Olah 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.
  • 9Posner 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.
  • 10徐嵩,徐世平,李兰敏.6-或7-(取代苯乙烯基)香豆素类化合物的合成及其抗癌活性的研究[J].药学学报,2000,35(2):103-107. 被引量:19

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