(2S,1'R)-N-tert-Butoxy-N-1'-(1''-naphthyl)ethyl 2-benzylpent-4-enamide | 1177266-29-3

• 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-benzylpent-4-enamide
• 英文别名: (2S)-2-benzyl-N-[(2-methylpropan-2-yl)oxy]-N-[(1R)-1-naphthalen-1-ylethyl]pent-4-enamide
• CAS: 1177266-29-3
• 化学式: C₂₈H₃₃NO₂
• 分子量: 415.576
• InChiKey: APHXIYIDCHRHAJ-QPPBQGQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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-benzylpent-4-enamide 在 水 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以92%的产率得到trans-2-(benzyl)-4-(iodomethyl)-γ-butyrolactone
  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)ethyl pent-4-enamide 、 溴甲苯 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以91%的产率得到(2S,1'R)-N-tert-Butoxy-N-1'-(1''-naphthyl)ethyl 2-benzylpent-4-enamide
  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.