(R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-allyloxyacetamide | 1234713-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-allyloxyacetamide
• CAS: 1234713-88-2
• 化学式: C₂₁H₂₇NO₃
• 分子量: 341.45
• InChiKey: IHXPEMXLYCAORT-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-allyloxyacetamide 、 碘甲烷 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 以100%的产率得到(R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl (S)-2-allyloxypropanamide
  参考文献：
  名称：

  Alkylation and aldol reactions of acyl derivatives of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes

  摘要：

  Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates alpha-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol products with high levels of diastereoselectivity. These adducts may be reductively cleaved with LiAlH(4) to give enantiopure alpha-alkoxy-, alpha-substituted-beta-alkoxy- and alpha,beta-dialkoxyaldehydes in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.105
• 作为产物：
  描述：

  (R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-bromoacetamide 、 烯丙醇 在 sodium hydride 、 15-冠醚-5 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 以75%的产率得到(R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-allyloxyacetamide
  参考文献：
  名称：

  Alkylation and aldol reactions of acyl derivatives of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes

  摘要：

  Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates alpha-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol products with high levels of diastereoselectivity. These adducts may be reductively cleaved with LiAlH(4) to give enantiopure alpha-alkoxy-, alpha-substituted-beta-alkoxy- and alpha,beta-dialkoxyaldehydes in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.105