(2S,1'R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-(ortho-bromobenzyl)propanamide | 1177266-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,1'R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-(ortho-bromobenzyl)propanamide
• 英文别名: (2S)-3-(2-bromophenyl)-2-methyl-N-[(2-methylpropan-2-yl)oxy]-N-[(1R)-1-naphthalen-1-ylethyl]propanamide
• CAS: 1177266-23-7
• 化学式: C₂₆H₃₀BrNO₂
• 分子量: 468.434
• InChiKey: SURBXQCNICPTHT-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (2S,1'R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-(ortho-bromobenzyl)propanamide 在 叔丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以85%的产率得到(S)-2-methyl-1-indanone
  参考文献：
  名称：

  The Chiral Auxiliary N-1-(1′-Naphthyl)ethyl-O-tert-butylhydroxylamine: A Chiral Weinreb Amide Equivalent

  摘要：

  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.

  DOI：

  10.1021/ol901174t
• 作为产物：
  描述：

  (R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethylpropanamide 、 2-溴溴苄 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以71%的产率得到(2S,1'R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 2-(ortho-bromobenzyl)propanamide
  参考文献：
  名称：

  The Chiral Auxiliary N-1-(1′-Naphthyl)ethyl-O-tert-butylhydroxylamine: A Chiral Weinreb Amide Equivalent

  摘要：

  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.

  DOI：

  10.1021/ol901174t

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.