(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N,2-dimethylpentanamide | 177324-97-9

• 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: (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N,2-dimethylpentanamide
• CAS: 177324-97-9
• 化学式: C₁₄H₃₁NO₃Si
• 分子量: 289.491
• InChiKey: LKUGUTAGXPKKAR-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N,2-dimethylpentanamide 在 四丁基氟化铵 、 sodium acetate 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 (4R,5S)-(-)-4-methyl 5-hydroxy heptan 3-one
  参考文献：
  名称：

  Asymmetric aldol condensation as a route to polypropionate derived pheromones

  摘要：

  The synthesis of the polypropionate-derived pheromones sitophilate (1) and sitophilure (2) are described using an asymmetric aldol condensation as the key step to adduct 6; compound 6 was smoothly converted to the antipodes of each pheromone. This procedure can be expanded to more complicated structures with the same type of syn configuration such as stegobinone (3) and serricornin (4). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00021-1
• 作为产物：
  描述：

  (4R,5S)-N-<(2'R,3'S)-3'-hydroxy-2'-methyl-1'-oxopentyl>-4-methyl-5-phenyl-2-oxazolidinone 在 咪唑 、 三甲基铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N,2-dimethylpentanamide
  参考文献：
  名称：

  Asymmetric aldol condensation as a route to polypropionate derived pheromones

  摘要：

  The synthesis of the polypropionate-derived pheromones sitophilate (1) and sitophilure (2) are described using an asymmetric aldol condensation as the key step to adduct 6; compound 6 was smoothly converted to the antipodes of each pheromone. This procedure can be expanded to more complicated structures with the same type of syn configuration such as stegobinone (3) and serricornin (4). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00021-1

文献信息

• Asymmetric aldol condensation as a route to polypropionate derived pheromones
  作者：J DiBattista

  DOI：10.1016/0968-0896(96)00021-1

  日期：1996.3

  The synthesis of the polypropionate-derived pheromones sitophilate (1) and sitophilure (2) are described using an asymmetric aldol condensation as the key step to adduct 6; compound 6 was smoothly converted to the antipodes of each pheromone. This procedure can be expanded to more complicated structures with the same type of syn configuration such as stegobinone (3) and serricornin (4). Copyright (C) 1996 Elsevier Science Ltd