(2RS,3SR)-3-methoxy-2-methyl-butyric acid methyl ester | 39788-67-5

• 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: (2RS,3SR)-3-methoxy-2-methyl-butyric acid methyl ester
• 英文别名: methyl (2S,3R)-3-methoxy-2-methylbutanoate
• CAS: 39788-67-5
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: QBVNKCPJUNWGOJ-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-3-methoxy-2-methyl-butyric acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (+)-erythro-3-Methoxy-2-methylbutanol-(1)
  参考文献：
  名称：

  甲氧基苯硫醚的立体化学

  摘要：

  邻苯二酚RCH（OMe）·CHMe·[CH 2 ] 4 ·CH（OH）·CH 2 ·CH（OH）·[CH 2 ] n Me（R = Et或Me，n = 20和22），组成通过用H代替每个OH，可将一部分结核脂质转化为相应的甲氧基苯硫醚铈烷A和B（分别为R = Et或Me）。已经合成了后者的旋光性非对映异构体和与结构相关的模型化合物。通过比较甲氧基苯硫杂环戊烷与合成产物，将带有甲氧基和甲基支链的不对称中心分配为苏-构型，按照在JCS Perkin I中定义的意义使用苏-，1973，109。

  DOI：

  10.1039/p19730001117
• 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 (2RS,3SR)-3-methoxy-2-methyl-butyric acid methyl ester
  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

• Studies in the stereochemistry of 2-alkyl-3-hydroxy- and 2-alkyl-3-methoxy-butyric acids
  作者：K. Maskens、N. Polgar

  DOI：10.1039/p19730000109

  日期：——

  3-hydroxy-2-methyl- and 3-methoxy-2-methyl-butyric acids resulting on demercuriation of mercuric acetate adducts of 2-methylbut-2-enoic acids have been studied, and their i.r., n.m.r., and mass spectrometric properties compared with those of the diastereoisomeric ethyl 2-allyl-3-hydroxy- and 3-hydroxy-2-propylbutyrates. Demercuriation of the mercuric acetate adducts of tiglic acid with sodium borohydride is found to

  研究了由2-甲基丁-2-烯酸的乙酸汞加合物去汞而生成的非对映异构体3-羟基-2-甲基-和3-甲氧基-2-甲基-丁酸，其ir，nmr和质谱与非对映异构体2-烯丙基-3-羟基-和3-羟基-2-丙基丁酸酯的性质相比。已发现，叔丁基酸的乙酸汞的乙酸加合物与硼氢化钠的脱汞得到非对映异构体产物的混合物，而与硫化氢的脱汞基本上仅产生这些非对映异构体中的一种。提供了有关这些产品配置的证据。解决了3-甲氧基-2-甲基丁酸的非对映异构体，该异构体通过硫化氢脱汞而形成了叔丁酸的乙酸汞乙酸加合物通过奎宁盐。
• 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
• 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
  作者：Yvan Guindon、J. Rancourt

  DOI：10.1021/jo980636x

  日期：1998.9.1

  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.