Ethyl (2R,3R)-3-methyl-2-oxiranecarboxylate | 19780-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: Ethyl (2R,3R)-3-methyl-2-oxiranecarboxylate
• 英文别名: ethyl (2S,3S)-3-methyloxirane-2-carboxylate；ethyl trans-3-methyl-1-oxirane-2-carboxylate；ethyl 3-methyloxirane-2-carboxylate；ethyl (2R,3S)- and (2S,3S)-2,3-epoxybutanoate
• CAS: 19780-35-9；25834-24-6；36099-48-6；38053-37-1；58917-48-9；82769-14-0；110508-08-2；118712-09-7；136889-93-5
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: VYXHEFOZRVPJRK-ROLXFIACSA-N

物化性质

• 沸点：
  77 °C (20 mmHg)
• 密度：
  1.099±0.06 g/cm3(Predicted)
• 闪点：
  45 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  Ethyl (2R,3R)-3-methyl-2-oxiranecarboxylate 生成 (-)-(2R,3S)-2,3-epoxybutyric acid
  参考文献：
  名称：

  Determination of absolute structure of (−)-oudemansin b

  摘要：

  DOI：

  10.1016/s0040-4039(00)85221-1
• 作为产物：
  描述：

  2-氯乙酰乙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 Ethyl (2R,3R)-3-methyl-2-oxiranecarboxylate
  参考文献：
  名称：

  Determination of absolute structure of (−)-oudemansin b

  摘要：

  DOI：

  10.1016/s0040-4039(00)85221-1

文献信息

• Practical Synthesis of Optically Pure Methyl (2<i>R</i>,3<i>S</i>)-2,3-Epoxybutanoate via Microbial Asymmetric Reduction of α-Chloroacetoacetate
  作者：Hiroyuki Akita、Reiko Todoroki、Hiroshi Endo、Yoshinobu Ikari、Takeshi Oishi

  DOI：10.1055/s-1993-25895

  日期：——

  Asymmetric reduction of ethyl α-chloroacetoacetate (3) with Baker's yeast followed by treatment with sodium ethoxide afforded a mixture of ethyl (2R,3S)-( 8) and (2S,3S)-2,3-epoxybutanoate (9) (8/9, 85:15), which could be converted into the optically pure methyl (2R,3S)-2,3-epoxybutanoate (25) via one recrystallization of the brucine salt of the diastereomeric mixture of the corresponding epoxy acid.

  用贝克酵母不对称还原δ-氯乙酰乙酸乙酯（3），然后用乙醇钠处理，得到(2R,3S)-( 8)和(2S,3S)-2,3-环氧丁酸乙酯（9）的混合物（8/9，85：通过对相应环氧酸非对映异构体混合物的布鲁氨酸盐进行一次重结晶，可将其转化为光学纯度较高的 (2R,3S)-2,3-环氧丁酸甲酯 (25)。
• Reaction of caesium 4-chlorophenate and chlorohydrins from threonines: synthesis of clofibrate analogues
  作者：Maria Grazia Perrone、Ernesto Santandrea、Leonardo Di Nunno、Antonio Scilimati、Vincenzo Tortorella、Francesco Capitelli、Valerio Bertolasi

  DOI：10.1016/j.tetasy.2005.01.006

  日期：2005.2

  Clofibrate is a well-known peroxisome prolifierator-activated receptor-alpha (PPARalpha) agonist, used in the treatment of hyperlipaemias and atherosclerosis and to prevent heart failure. Herein, the preparation of the four enantiomerically pure stereoisomers of ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate as clofibrate analogues is described. Biological evaluation of these new compounds was performed by a transactivation assay in a transiently transfected monkey kidney fibroblast cell line. All four diastereomers were inactive even at 300 muM, where clofibrate showed an evident activity, suggesting that the designed clofibrate molecular structural modifications in the analogues caused the loss of peroxisome proliferator-activated receptor-alpha (PPARalpha) activity. (C) 2005 Elsevier Ltd. All rights reserved.