Methyl 3-hydroxy-2,3-dimethylhexanoate | 1248194-56-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 3-hydroxy-2,3-dimethylhexanoate
• CAS: 1248194-56-0
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: YPDWEFZWIGPMNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯丙酸甲酯 、 2-戊酮 在 tris(2,2'-bipyridine)nickel(II) tetrafluoroborate 、 四丁基溴化铵 、 zinc dibromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到Methyl 3-hydroxy-2,3-dimethylhexanoate
  参考文献：
  名称：

  Metal exchange between an electrogenerated organonickel species and zinc halide: application to an electrochemical, nickel-catalyzed Reformatsky reaction

  摘要：

  The mechanism of the electroreductive coupling of alpha-chloro esters or alpha-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques. The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the alpha-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent. The electrosynthesis of various beta-hydroxy esters, beta-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.

  DOI：

  10.1021/jo00006a012

文献信息

• Iron-Mediated Electrochemical Reaction of α-Chloroesters with Carbonyl Compounds
  作者：Muriel Durandetti、Clothilde Meignein、Jacques Périchon

  DOI：10.1021/ol0273046

  日期：2003.2.1

  Reformatsky-type reactions have been performed efficiently using an electroassisted iron-complex catalysis. Valuable product such as beta-hydroxyesters, ketones or nitriles are thus prepared with high yields.
• Metal exchange between an electrogenerated organonickel species and zinc halide: application to an electrochemical, nickel-catalyzed Reformatsky reaction
  作者：Annie Conan、Soline Sibille、Jacques Perichon

  DOI：10.1021/jo00006a012

  日期：1991.3

  The mechanism of the electroreductive coupling of alpha-chloro esters or alpha-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques. The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the alpha-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent. The electrosynthesis of various beta-hydroxy esters, beta-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.