(S)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl (R)-2-benzyloxyheptanamide | 1234714-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl (R)-2-benzyloxyheptanamide
• CAS: 1234714-06-7
• 化学式: C₃₀H₃₉NO₃
• 分子量: 461.645
• InChiKey: QMQULNFBBWUXRL-NEKDWFFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-碘戊烷 、 (S)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-benzyloxyacetamide 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到(S)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl (R)-2-benzyloxyheptanamide
  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