(3RS,4RS,5RS)-3,4-Epoxy-5-methyldihydro-2(3H)-furanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (3RS,4RS,5RS)-3,4-Epoxy-5-methyldihydro-2(3H)-furanone
• 英文别名: (1S,4S,5S)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-one
• 化学式: C₅H₆O₃
• 分子量: 114.101
• InChiKey: LWQJEOVXSWEZFZ-HZLVTQRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3RS,4RS,5RS)-3,4-Epoxy-5-methyldihydro-2(3H)-furanone 在 copper(l) iodide 、 正丁基锂 、 二异丙胺 作用下， 以 吡啶 、 正己烷 为溶剂， 反应 27.08h， 生成 (-)-blastmycinone
  参考文献：
  名称：

  Ortuno, R. M.; Cardellach, J.; Font, J., Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 79 - 84

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基-2(5H)-呋喃酮 在 sodium hypochlorite 作用下， 以 吡啶 为溶剂， 以54%的产率得到(3RS,4RS,5RS)-3,4-Epoxy-5-methyldihydro-2(3H)-furanone
  参考文献：
  名称：

  Highly stereo and regiocontrolled synthesis of both racemic and optically active (−)-blastmycinone

  摘要：

  DOI：

  10.1016/s0040-4039(00)94920-7

文献信息

• A convergent total synthesis of epolactaene: an application of the bridgehead oxiranyl anion strategy
  作者：Kouji Kuramochi、Seigo Nagata、Hideyoshi Itaya、Yasuaki Matsubara、Takashi Sunoki、Hiromi Uchiro、Ken-ichi Takao、Susumu Kobayashi

  DOI：10.1016/j.tet.2003.09.021

  日期：2003.12

  The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to the total synthesis of (+)-epolactaene and its analogs is described.

  描述了内酯衍生的环氧乙烷基阴离子的产生和反应。环氧内酯和醛的醛醇缩合反应通过三甲基甲硅烷基环氧内酯通过两步程序完成。描述了该方法在（+）-二十碳烯及其类似物的全合成中的应用。
• Generation and reaction of an oxiranyl anion derived from α,β-epoxy-γ-butyrolactone
  作者：Kouji Kuramochi、Hideyoshi Itaya、Seigo Nagata、Takao Ken-ichi、Susumu Kobayashi

  DOI：10.1016/s0040-4039(99)01511-7

  日期：1999.10

  Generation and reaction of an oxiranyl anion on a lactone are described. Aldol-type condensation of epoxylactone and aldehydes was accomplished by a two-step procedure via trimethylsilyl epoxylactone.

  描述了环氧乙烷基阴离子在内酯上的产生和反应。环氧内酯和醛的醛醇缩合反应通过三甲基甲硅烷基环氧内酯通过两步程序完成。
• Enantiomeric β-angelica lactone epoxides: their syntheses from suitable chiral precursors and their use in the preparation of blastmycinone
  作者：Rosa M. Ortuño、Daniel Alonso、Jaume Cardellach、Josep Font

  DOI：10.1016/s0040-4020(01)86801-0

  日期：1987.1

  Syntheses of (S)-β-angelica lactone from L-tartaric acid and (R)-γ-hydroxy-methyl-γ-butyrolactone, 5, are reported. Alternative routes to prepare 5 from S- and R-glutamic acids and D-ribonolactone, respectively, are also presented. Epoxides derived from (R)- and (S)-β-angelica lactones have been obtained and their use in the synthesis of both (+)- and (-)-blastmycinone, 24, has been established.

  报道了由L-酒石酸和（R）-γ-羟基-甲基-γ-丁内酯5合成（S）-β-当归内酯。还提出了分别由S-，R-谷氨酸和D-核糖内酯制备5的替代方法。已经获得了衍生自（R）-和（S）-β-当归内酯的环氧化物，并且已经确定了它们在合成（+）-和（-）-blastmycinone（24）中的用途。
• Structure–activity relationships of epolactaene analogs as DNA polymerases inhibitors
  作者：Kouji Kuramochi、Yoshiyuki Mizushina、Seigo Nagata、Fumio Sugawara、Kengo Sakaguchi、Susumu Kobayashi

  DOI：10.1016/j.bmc.2004.03.007

  日期：2004.5

  Epolactaene, a neuritogenic compound in human neuroblastoma cells, showed inhibitory activities against DNA polymerases alpha and beta. The synthesis and inhibitory activities of epolactaene analogs are described. The alpha,beta-epoxy-gamma-lactam moiety in the core and the length of the side chain greatly influenced the activities. Compound 5 was the strongest inhibitor of DNA polymerase a and 0 of all synthesized compounds with IC50 values of 13 and 78 muM, respectively. N- and O-alkyl derivatives that had modified core moieties showed moderate inhibition. (C) 2004 Elsevier Ltd. All rights reserved.
• Highly stereo and regiocontrolled synthesis of both racemic and optically active (−)-blastmycinone
  作者：J. Cardellach、J. Font、R.M. Ortuño

  DOI：10.1016/s0040-4039(00)94920-7

  日期：1985.1