(R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-bromoacetamide | 1234713-90-6

• 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-bromoacetamide
• 英文别名: 2-bromo-N-[(2-methylpropan-2-yl)oxy]-N-[(1R)-1-naphthalen-1-ylethyl]acetamide
• CAS: 1234713-90-6
• 化学式: C₁₈H₂₂BrNO₂
• 分子量: 364.282
• InChiKey: XTUQJINJCXTUBF-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-bromoacetamide 、 3,4-二甲氧基苄醇 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74%的产率得到(S)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-(3''',4'''-dimethoxybenzyloxy)acetamide
  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：

  溴乙酰溴 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以100%的产率得到(R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-bromoacetamide
  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

文献信息

• 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
  作者：Alexander N. Chernega、Stephen G. Davies、Ai M. Fletcher、Christopher J. Goodwin、David Hepworth、R. Shyam Prasad、Paul M. Roberts、Edward D. Savory、Andrew D. Smith、James E. Thomson

  DOI：10.1016/j.tet.2010.03.105

  日期：2010.6

  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.