(E,Z)-2-methyl-3-ethyl-2-oxiranecarboxylic acid | 80532-68-9

• 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: (E,Z)-2-methyl-3-ethyl-2-oxiranecarboxylic acid
• 英文别名: 3-Ethyl-2-methyloxirane-2-carboxylic acid
• CAS: 80532-68-9
• 化学式: C₆H₁₀O₃
• mdl: MFCD19229670
• 分子量: 130.144
• InChiKey: RZRRUPYVQGHVOX-UHFFFAOYSA-N

物化性质

• 沸点：
  221.6±33.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,Z)-2-methyl-3-ethyl-2-oxiranecarboxylic acid 在 indium(III) chloride 、 sodium azide 作用下， 以 水 为溶剂， 反应 8.0h， 生成 anti-3-Azido-2-hydroxy-2-methylpentanoic acid
  参考文献：
  名称：

  Azidolysis of α,β-Epoxycarboxylic Acids. A Water-Promoted Process Efficiently Catalyzed by Indium Trichloride at pH 4.0

  摘要：

  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.

  DOI：

  10.1021/jo015564f
• 作为产物：
  描述：

  丙醛 、 2-氯丙酸 在 lithium diisopropyl amide 作用下， 生成 2-chloro-2-methyl-3-hydroxypentanoic acid 、 (E,Z)-2-methyl-3-ethyl-2-oxiranecarboxylic acid
  参考文献：
  名称：

  Dianions derived from .alpha.-halo acids. The Darzens condensation revisited

  摘要：

  DOI：

  10.1021/jo00346a013

文献信息

• ANTIPERSPIRANT COMPOSITIONS
  申请人：Batchelor Stephen Norman

  公开号：US20120114582A1

  公开（公告）日：2012-05-10

  Antiperspirant compositions containing a pigment often exhibit a dull colour if an inorganic pigment is employed, but if many bright organic pigments are used, the pigment is subject to photodegradation and accordingly fades. By incorporating selected types of polycyclic organic pigment, namely an organic pigment containing condensed aromatic or heterocyclic ring system that is free from an azo substituent and does not comprise, a di or th-arylcarbonium, or a xanthene based pigment, the antiperspirant composition comprises a bright pigment that is resistant to photodegradation. The composition is preferably anhydrous and advantageously a firm stick.
• [EN] ANTIPERSPIRANT COMPOSITIONS<br/>[FR] COMPOSITIONS ANTISUDORIFIQUES
  申请人：UNILEVER PLC

  公开号：WO2010149531A2

  公开（公告）日：2010-12-29

  Antiperspirant compositions containing a pigment often exhibit a dull colour if an inorganic pigment is employed, but if many bright organic pigments are used, the pigment is subject to photodegradation and accordingly fades. By incorporating selected types of polycyclic organic pigment, namely an organic pigment containing condensed aromatic or heterocyclic ring system that is free from an azo substituent and does not comprise, a di or th-arylcarbonium, or a xanthene based pigment, the antiperspirant composition comprises a bright pigment that is resistant to photodegradation. The composition is preferably anhydrous and advantageously a firm stick.
• Dianions derived from .alpha.-halo acids. The Darzens condensation revisited
  作者：Carl R. Johnson、Thomas R. Bade

  DOI：10.1021/jo00346a013

  日期：1982.3
• 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.