ethyl 2-deuterio-3-hydroxybutanoate | 163980-39-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 2-deuterio-3-hydroxybutanoate
• 英文别名: Ethyl 2-deutero-3-hydroxybutanoate
• CAS: 163980-39-0
• 化学式: C₆H₁₂O₃
• 分子量: 133.152
• InChiKey: OMSUIQOIVADKIM-QYKNYGDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trimethoxonium tetrafluoroborate 、 ethyl 2-deuterio-3-hydroxybutanoate 在 1,8-双二甲氨基萘 作用下， 以 二氯甲烷 为溶剂， 生成 rel-(2R,3S)-ethyl 2-deuterio-3-methoxybutanoate 、 rel-(2S,3S)-ethyl 2-deuterio-3-methoxybutanoate
  参考文献：
  名称：

  Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates

  摘要：

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.

  DOI：

  10.1021/jo00042a029
• 作为产物：
  描述：

  ethyl 3-hydroxybutyrate 在 偶氮二异丁腈 、 triphenylstannane-d₁ 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 2-deuterio-3-hydroxybutanoate
  参考文献：
  名称：

  Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates

  摘要：

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.

  DOI：

  10.1021/jo00042a029

文献信息

• 1,2-Asymmetric induction in radical reactions. Deuteration and allylation reactions of β-oxy-α-bromo esters
  作者：Dennis P. Curran、P.S. Ramamoorthy

  DOI：10.1016/s0040-4020(01)80402-6

  日期：1993.5

  Chiral radicals were generated by halogen abstraction reactions of β-oxy-α-bromo esters and their asymmetric deuteration and allylation reactions were studied.

  通过β-氧基-α-溴代酸酯的卤素抽象反应生成手性自由基，并研究了它们的不对称氘代和烯丙基化反应。