methyl (2S*,3S*)-3-methoxy-2-methylbutanoate | 39788-68-6

• 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 (2S*,3S*)-3-methoxy-2-methylbutanoate
• 英文别名: methyl (2S,3S)-3-methoxy-2-methylbutanoate
• CAS: 39788-68-6
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: QBVNKCPJUNWGOJ-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  惕各酸甲酯 在 三乙基硼 、 溴 、 三正丁基氢锡 、 silver nitrate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl (2S*,3S*)-3-methoxy-2-methylbutanoate
  参考文献：
  名称：

  The Use of Lewis Acids in Radical Chemistry. Chelation-Controlled Radical Reductions of Substituted α-Bromo-β-alkoxy Esters and Chelation-Controlled Radical Addition Reactions

  摘要：

  The radical reduction of a series of alpha-bromo-beta-alkoxy esters under chelation-controlled conditions is reported. Proceeding with high stereoselectivity in the presence of MgBr2. OEt2, reductions give access to syn, products. Systematic variations in substrate substituents show that these reactions tolerate a wide variety of alkyl functionalities at positions 2 and 3 and are relatively unaffected by the nature of the ester group. Changes to the alkoxy function indicate that a bidentate chelate is involved in the reaction and that an excess of MgBr2. OEt2 is required for optimum selectivity by favoring this species in preference to the anti-selective monodentate or nonchelated pathways. Competition experiments suggest that the monodentate pathway is kinetically favored over the bidentate one. The suppressibility of the reaction by radical chain inhibitors and the need for initiation indicate the intermediacy of radicals. Further support for this mechanism includes both radical addition to alpha,beta-unsaturated esters and reduction of bromides conducted in the presence of a Lewis acid.

  DOI：

  10.1021/jo980636x

文献信息

• Stereoselective demercuration of α-mercuriocarboxylates
  作者：Frederick H. Gouzoules、Ralph Allen Whitney

  DOI：10.1016/s0040-4039(00)98659-3

  日期：1985.1
• The palladium(II) catalyzed olefin carbonylation reaction. The stereochemistry of methoxypalladation
  作者：D. E. James、L. F. Hines、J. K. Stille

  DOI：10.1021/ja00423a027

  日期：1976.3
• Factors affecting diastereoselectivity in the protiodemercuration of .alpha.-mercurio carbonyl compounds
  作者：Frederick H. Gouzoules、Ralph Allen Whitney

  DOI：10.1021/jo00361a016

  日期：1986.5