methyl α,β-epoxycyclohexanecarboxylate | 17550-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: methyl α,β-epoxycyclohexanecarboxylate
• 英文别名: Methyl 1,2-epoxycyclohexanecarboxylate；1,2-epoxy-cyclohexanecarboxylic acid methyl ester；Methyl 7-oxabicyclo[4.1.0]heptane-1-carboxylate
• CAS: 17550-59-3
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: AJMGIOJRUFPGTD-UHFFFAOYSA-N

物化性质

• 沸点：
  73-76 °C(Press: 6 Torr)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  methyl α,β-epoxycyclohexanecarboxylate 在 1-羧甲基-3-甲基咪唑溴盐 作用下， 反应 1.5h， 以85%的产率得到2-bromo-1-hydroxycyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Ionic Liquid as Reagent. A Green Procedure for the Regioselective Conversion of Epoxides to Vicinal-Halohydrins Using [AcMIm]X under Catalyst- and Solvent-Free Conditions

  摘要：

  A variety of structurally diverse epoxides undergo facile cleavages by ionic liquid, [AcMIm]X without any catalyst and solvent to produce the corresponding vicinal halohydrins in high yields. The cleavages are considerably fast and highly regioselective.

  DOI：

  10.1021/jo0500885
• 作为产物：
  描述：

  环己甲酸甲酯 在 苯基氯化硒 、 4,4'-硫联二(6-叔丁基-2-甲基苯酚) 、 双氧水 、 溶剂黄146 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 methyl α,β-epoxycyclohexanecarboxylate
  参考文献：
  名称：

  氮丙啶-2-羧酸酯的便捷合成

  摘要：

  用叠氮化钠处理由使用Sharpless环氧化的烯丙基醇制备的旋光环氧乙烷-2-羧酸酯。随后通过与三苯基膦反应以高收率和高光学纯度将获得的叠氮基醇转化为氮丙啶-2-羧酸酯。使各种外消旋环氧乙烷-2-羧酸酯进行相同的反应顺序。

  DOI：

  10.1002/recl.19921110101

文献信息

• Method for producing polydienes and polydiene copolymers with reduced cold flow
  申请人：BRIDGESTONE CORPORATION

  公开号：US10301397B2

  公开（公告）日：2019-05-28

  A method for preparing a coupled polymer, the method comprising the steps of (i) polymerizing monomers to form a reactive polymer, and (ii) reacting the reactive polymer with a glycidic ester.

  一种制备偶联聚合物的方法，该方法包括以下步骤：(i) 单体聚合形成活性聚合物，(ii) 活性聚合物与缩水甘油酯反应。
• Preparation of allylic alcohols from epoxides using iodotrimethylsilane
  作者：George A. Kraus、Kevin Frazier

  DOI：10.1021/jo01301a006

  日期：1980.6
• Azidolysis of α,β-Epoxycarboxylic Acids. A Water-Promoted Process Efficiently Catalyzed by Indium Trichloride at pH 4.0
  作者：Francesco Fringuelli、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/jo015564f

  日期：2001.5.1

  The catalytic efficiency of InCl3, Yb(OTf)(3), and Sc(OTf)(3) in the azidolysis of alpha,beta -epoxycarboxylic acids has been studied in water and in organic solvents, for comparison using NaN3 and Me3SiN3 as the source of the azido group. In water, the catalytic effectiveness of these metal salts strongly depends on the pH of the aqueous medium and on the type of Lewis acid catalyst. In water their catalytic activity is mostly due to the corresponding aqua ion species, the concentration of which becomes significant when the pH of the aqueous medium is below the corresponding pK(1,1) hydrolysis constant. The process is more efficient in water than in organic solvents. At pH 4.0, InCl3 is a far better catalyst than Yb(OTf)(3) or Sc(OTf)(3) and allows the highly regio- and diasteroselective preparation of beta -azido-alpha -hydroxycarboxylic acids, which can be isolated in pure form in very high yields.
• KRAUS G. A.; FRAZIER K., J. ORG. CHEM., 1980, 45, NO 13, 2579-2581
  作者：KRAUS G. A.、 FRAZIER K.

  DOI：——

  日期：——
• Method for isomerization a glycidate derivative
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0153692B1

  公开（公告）日：1992-07-29