cis-2,3-epoxybutane-1,4-diacetate | 136258-90-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-2,3-epoxybutane-1,4-diacetate
• 英文别名: [(2R,3S)-3-(acetyloxymethyl)oxiran-2-yl]methyl acetate
• CAS: 136258-90-7
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: ZCNLOFYSBLYNSY-OCAPTIKFSA-N

物化性质

• 沸点：
  252.4±15.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-2,3-epoxybutane-1,4-diacetate 在 吡啶盐酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到Acetic acid 4-acetoxy-2-chloro-3-hydroxy-butyl ester
  参考文献：
  名称：

  Cotterill, Ian C.; Shelton, Michael C.; Machemer, Daniel E. W., Journal of the Chemical Society. Perkin transactions I, 1998, # 7, p. 1335 - 1341

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-1,4-二乙酰氧基-2-丁烯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以98%的产率得到cis-2,3-epoxybutane-1,4-diacetate
  参考文献：
  名称：

  Pheromone Synthesis; CXXXIX.¹Enzymatic Preparation of (2S,3R)-4-Acetoxy-2,3-epoxybutan-1-ol and Its Conversion to the Epoxy Pheromones of the Gypsy Moth and the Ruby Tiger Moth

  摘要：

  在猪胰脂肪酶催化下，1, 4-二乙酰氧基-顺式-2,3-环氧丁烷发生不对称水解，生成 (2S,3R) -4-乙酰氧基-2,3-环氧布坦-1-醇，并转化为两种天然环氧化物： 吉普赛蛾信息素 disparlure [(7R,8S)-7,8-epoxy-2-methyloctadecane] 和红宝石虎蛾信息素 [(6Z,9S,10R)-9,10-epoxy-6-henicosene]。

  DOI：

  10.1055/s-1992-26290

文献信息

• EPOXIDATION OF OLEFINS AT LOW TEMPERATURE USING <i>m</i>-CHLOROPERBENZOIC ACID*
  作者：R. Srinivasan、M. Chandrasekharam、P. V. S. N. Vani、A. Seema Chida、A. K. Singh

  DOI：10.1081/scc-120004069

  日期：2002.1.1

  Epoxidation of olefins using m-chloroperbenzoic acid in dichloromethane without catalyst at low temperature Is described.
• Mori, Kenji, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 5, p. 393 - 406
  作者：Mori, Kenji

  DOI：——

  日期：——
• Influence of ester chain length, enzyme, and physical parameters on lipase-catalysed hydrolyses of meso-oxiranedimethanol esters. Part 2
  作者：Jonathan D Moseley、James Staunton

  DOI：10.1016/s0957-4166(00)00276-7

  日期：2000.8

  A range of meso-oxiranedimethanol diesters were prepared and subjected to hydrolysis by a selection of microbial and porcine-derived lipases. The best chain length was then subjected to a wider range of lipases. The physical reaction parameters were further investigated for the best enzyme/substrate combination. The results revealed the effects of ester chain length, choice of enzyme, and physical reaction parameters on the enzymic hydrolysis. Using a combination of the these three variables, it is demonstrated that this is a versatile approach for the optimisation of an enzymic hydrolysis for a given substrate. Additionally, we also report on an efficient, multigram synthesis of oxiranedimethanol diesters from cheap achiral precursors, their successful enzymic hydrolyses to alcohols in good chemical yield and e.e., and their conversion to synthetically useful aldehydes in high yield. Both enantiomeric series can readily be accessed from a single enzymic hydrolysis result. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Influence of ester chain length on lipase catalysed hydrolyses of meso-oxiranedimethanol esters
  作者：Jonathan D. Moseley、James Staunton

  DOI：10.1016/s0957-4166(98)00374-7

  日期：1998.10

  A range of meso-oxiranedimethanol diesters have been hydrolysed by a selection of microbial and porcine derived lipases. The results reveal the effects of ester substitution, particularly chain length, on the hydrolyses. General conclusions are made which demonstrate that ester chain length can be 'tuned' to achieve optimum enantiomeric enrichment for a given substrate. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of optically pure cis epoxyalcohols via an enzymatic route; an alternative to the sharpless epoxidation.
  作者：D. Grandjean、P. Pale、J. Chuche

  DOI：10.1016/0040-4039(91)80682-v

  日期：1991.6

  Optically pure (2S, 3R)-4-butyryloxy-2,3-epoxybutan-1-ol 2b and (2R, 3S)-4-tert-butyldiphenylsilyoxy-2,3-epoxybutan-1-ol 5, starting materials for the synthesis of enantiomeric epoxyalcohols 3 and 4 were obtained after enzymatic hydrolysis of meso cis-2,3-epoxybutane-1,4-diol diesters 1b.