(2S,3R)-3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)oxirane-2-carbaldehyde | 256494-35-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R)-3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)oxirane-2-carbaldehyde
• 英文别名: (2S,3R)-3-[3-[tert-butyl(diphenyl)silyl]oxypropyl]oxirane-2-carbaldehyde
• CAS: 256494-35-6
• 化学式: C₂₂H₂₈O₃Si
• 分子量: 368.548
• InChiKey: QUTRQILZSUMMSK-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  醋酸叔丁酯 、 (2S,3R)-3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)oxirane-2-carbaldehyde 在 lithium diisopropyl amide 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 生成 (3R,4R,5R)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate 、 (3S,4R,5R)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate
  参考文献：
  名称：

  Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes

  摘要：

  Aldol condensations on alpha-,beta-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and sny gamma,delta-epoxy beta-hydroxyesters and their NMR and IR spectrostroscopic properties. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00844-3
• 作为产物：
  描述：

  (E)-6-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)hex-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 pyridine-SO3 complex 、 二甲基亚砜 、 (-)-diethyl tartrate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,3R)-3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)oxirane-2-carbaldehyde
  参考文献：
  名称：

  Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes

  摘要：

  Aldol condensations on alpha-,beta-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and sny gamma,delta-epoxy beta-hydroxyesters and their NMR and IR spectrostroscopic properties. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00844-3

文献信息

• Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes
  作者：Kassoum Nacro、Michel Baltas、Liliane Gorrichon

  DOI：10.1016/s0040-4020(99)00844-3

  日期：1999.12

  Aldol condensations on alpha-,beta-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and sny gamma,delta-epoxy beta-hydroxyesters and their NMR and IR spectrostroscopic properties. (C) 1999 Elsevier Science Ltd. All rights reserved.