tert-butyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-phenylselanylpropanoate | 199384-37-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: tert-butyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-phenylselanylpropanoate
• CAS: 199384-37-7
• 化学式: C₁₈H₂₆O₄Se
• 分子量: 385.362
• InChiKey: YVUMMLMFAFBESK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-phenylselanylpropanoate 在 三乙基硼 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 tert-butyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate 、
  参考文献：
  名称：

  The Exocyclic Effect:  Protecting Group Strategy to Enhance Stereoselectivity in Hydrogen Transfer Reactions of Acyclic Free Radicals

  摘要：

  To enhance the diastereoselectivity of the hydrogen transfer reaction of acyclic substrates bearing 1,2- or 1,3-diols, the feasibility of a strategy employing bifunctional protecting groups has been demonstrated. This strategy is based upon the "exocyclic effect" or the significant improvement of anti-selectivity exhibited by the reductions of substrates in which the two substituents (R-1 and Y) at the stereogenic center alpha to the radical center are linked together. A rationale for the excellent facial discrimination of these exocyclic radicals is offered based on an analysis of transition state models, which considers both steric and electronic factors.

  DOI：

  10.1021/jo971595s
• 作为产物：
  描述：

  2-溴丙酸叔丁酯 在 sodium tetrahydroborate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 反应 1.33h， 生成 tert-butyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-phenylselanylpropanoate
  参考文献：
  名称：

  The Exocyclic Effect:  Protecting Group Strategy to Enhance Stereoselectivity in Hydrogen Transfer Reactions of Acyclic Free Radicals

  摘要：

  To enhance the diastereoselectivity of the hydrogen transfer reaction of acyclic substrates bearing 1,2- or 1,3-diols, the feasibility of a strategy employing bifunctional protecting groups has been demonstrated. This strategy is based upon the "exocyclic effect" or the significant improvement of anti-selectivity exhibited by the reductions of substrates in which the two substituents (R-1 and Y) at the stereogenic center alpha to the radical center are linked together. A rationale for the excellent facial discrimination of these exocyclic radicals is offered based on an analysis of transition state models, which considers both steric and electronic factors.

  DOI：

  10.1021/jo971595s