(2R,3R)-2,3-环氧-3-甲基丙酸乙酯 | 118712-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: (2R,3R)-2,3-环氧-3-甲基丙酸乙酯
• 英文名称: ethyl (2R,3R)-3-methyloxirane-2-carboxilate
• 英文别名: ethyl (2R,3R)-3-methyloxirane-2-carboxylate；Ethyl (2R,3R)-2,3-epoxybutanoate
• CAS: 118712-09-7
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: VYXHEFOZRVPJRK-RFZPGFLSSA-N

物化性质

• 沸点：
  172-174°C/760mmHg
• 稳定性/保质期：

  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (2R,3R)-2,3-环氧-3-甲基丙酸乙酯 以72%的产率得到
  参考文献：
  名称：

  LARCHEVEQUE, M.;PETIT, Y., JANSSEN CHIM. ACTA., 8,(1990) N, C. 10-11

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-bis<(trimethylsilyl)oxy>-1-ethoxy-butene 在 三乙胺 、 zinc(II) chloride 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 生成 (2R,3R)-2,3-环氧-3-甲基丙酸乙酯
  参考文献：
  名称：

  Synthesis and reactions of 3-hydroxy-2-nosyloxy esters produced by the stereoselective reduction of 2-nosyloxy-3-keto esters

  摘要：

  The reduction of 2-nosyloxy-3-keto esters is an effective method for the preparation of 3-hydroxy-2-nosyloxy esters. The reduction is stereoselective for the syn isomer. The anti isomer can be produced as the major product by the addition of p-nitrobenzenesulfonyl peroxide to ketene bis-silyl acetal derivatives of 3-hydroxy esters. The diastereomers are separable chromatographically and can be converted stereospecifically to glycidic esters and 2-azido-3-hydroxy esters. As such they appear to have excellent potential as versatile synthetic intermediates for the synthesis of 1,2,3-trifunctional substances.

  DOI：

  10.1021/jo00024a013

文献信息

• The Synthesis of Solvent-Free Glycidic Esters from Diazoesters and Carbonyl Compounds Catalysed by Lanthanide Triflates
  作者：Massimo Curini、Francesco Epifano、Maria Carla Marcotullio、Ornelio Rosati

  DOI：10.1002/1099-0690(200205)2002:9<1562::aid-ejoc1562>3.0.co;2-q

  日期：2002.5

  and carbonyl compounds catalysed by lanthanide triflates are described. Aldehydes, and α-unsubstituted and α-monosubstituted cyclohexanones react to give the selective formation of α,β-epoxy esters (glycidic esters), whereas other ketones are unreactive. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  描述了重氮化镧三氟甲磺酸酯催化的重氮乙酸乙酯与羰基化合物之间反应的结果。醛与α-未取代和α-单取代的环己酮反应生成α，β-环氧酯（缩水甘油酯）的选择性形成，而其他酮则没有反应性。（©Wiley-VCH Verlag GmbH，69451 Weinheim，Germany，2002）
• [EN] ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：HAPLOGEN GMBH

  公开号：WO2018050631A1

  公开（公告）日：2018-03-22

  The present invention relates to novel compounds of general formula (I) wherein the groups X, and R1 to R4 have the meanings given in the description and claims, process for preparing these compounds and their use as for treating, preventing or ameliorating viral infections and their use for treating, preventing or ameliorating diseases which are associated with PLA2G16.

  本发明涉及一般式（I）的新化合物，其中X和R1至R4基团的含义如描述和索赔中所述，制备这些化合物的方法以及它们作为治疗、预防或改善病毒感染的用途，以及用于治疗、预防或改善与PLA2G16相关的疾病的用途。
• A Convenient Synthesis of Enantiomerically Pure (2<i>R</i>,3<i>S</i>)- and (2<i>S</i>,3<i>R</i>)-3-Hydroxy-2-methylbutanoic Esters
  作者：Yves Petit、Caroline Sanner、Marc Larchevêque

  DOI：10.1055/s-1988-27629

  日期：——

  Both enantiomers of erythro methyl or ethyl 3-hydroxy-2-methylbutanoate were prepared by reaction of lithium dimethylcuprate with enantiomerically pure cis-2,3-epoxybutanoic esters derived from L- or D- threonine.

  两种对映体的赤霉醇或乙基3-羟基-2-甲基丁酸酯是通过锂二甲基铜盐与来源于L-或D-苏氨酸的对映体纯的顺式-2,3-环氧丁酸酯的反应制备的。
• Diastereocontrolled Synthesis of (-)-Codonopsinine
  作者：Marc Larchevêque、Mansour Haddad

  DOI：10.1055/s-2003-36777

  日期：——

  An efficient process is described for the total synthesis of the alkaloid (-)-codonopsinine. The synthetic strategy is based on the diastereoselective hydrocyanation of a 2,3-dialkoxyaldehyde derived from L-threonine followed by a reductive alkylation of the nitrile function with a Grignard compound and sodium borohydride. The resulting aminotriol was then cyclized into the target molecule after selective

  描述了生物碱 (-)-codonopsinine 的全合成的有效方法。合成策略基于衍生自 L-苏氨酸的 2,3-二烷氧基醛的非对映选择性氢氰化，然后用格氏化合物和硼氢化钠对腈官能团进行还原烷基化。得到的氨基三醇在选择性甲磺酰化后环化成目标分子。
• 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.