(1R)-N-[(2-methylpropan-2-yl)oxy]-1-naphthalen-1-ylethanamine | 1177266-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R)-N-[(2-methylpropan-2-yl)oxy]-1-naphthalen-1-ylethanamine
• CAS: 1177266-32-8
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: AZFJRZYPVPWZCF-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-N-tert-butoxy-N-1-(1-naphthyl)ethyl (2S,3R)-2-allyloxy-3-methoxy-3-phenylpropanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(1R)-N-[(2-methylpropan-2-yl)oxy]-1-naphthalen-1-ylethanamine
  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

• The Chiral Auxiliary <i>N</i>-1-(1′-Naphthyl)ethyl-<i>O</i>-<i>tert</i>-butylhydroxylamine: A Chiral Weinreb Amide Equivalent
  作者：Alexander N. Chernega、Stephen G. Davies、Christopher J. Goodwin、David Hepworth、Wataru Kurosawa、Paul M. Roberts、James E. Thomson

  DOI：10.1021/ol901174t

  日期：2009.8.6

  The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in >98% ee, on a multigram (>25 g) scale. Conversion to a range of N-acyl derivatives, followed by highly diastereoselective alkylation (>= 94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (>98% de) after chromatography. Reductive cleavage with LlAlH(4) allows direct access to chiral aldehydes, and treatment with MeLi gives chiral methyl ketones in excellent enantiopurity (>= 94% ee). The auxiliary can be recovered in >98% ee and recycled.
• 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.