rel-(2R,3R)-ethyl 3-hydroxy-2,4,4-trimethyl-2-(phenylselenyl)pentanoate | 142612-29-1

• 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: rel-(2R,3R)-ethyl 3-hydroxy-2,4,4-trimethyl-2-(phenylselenyl)pentanoate
• 英文别名: ethyl (2S,3S)-3-hydroxy-2,4,4-trimethyl-2-phenylselanylpentanoate
• CAS: 142612-29-1；142612-30-4
• 化学式: C₁₆H₂₄O₃Se
• 分子量: 343.325
• InChiKey: DLZAQLKSDWXAAG-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rel-(2R,3R)-ethyl 3-hydroxy-2,4,4-trimethyl-2-(phenylselenyl)pentanoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到rel-(2S,3R)-ethyl 3-hydroxy-2,3,4,4-tetramethylpentanoate
  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 2-(phenylselanyl)propanoate 、 特戊醛 在 lithium diisopropyl amide 作用下， 生成 ethyl (2S,3R)-3-hydroxy-2,4,4-trimethyl-2-phenylselanylpentanoate 、 rel-(2R,3R)-ethyl 3-hydroxy-2,4,4-trimethyl-2-(phenylselenyl)pentanoate
  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