(R)-O-(tert-butyl)-N-(1-(naphthalen-1-yl)ethyl)hydroxylamine ((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate | 1177266-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-O-(tert-butyl)-N-(1-(naphthalen-1-yl)ethyl)hydroxylamine ((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate
• CAS: 1177266-33-9
• 化学式: C₁₀H₁₆O₄S*C₁₆H₂₁NO
• 分子量: 475.649
• InChiKey: JUCLGMCKVJOLKA-QQUOSFJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-O-(tert-butyl)-N-(1-(naphthalen-1-yl)ethyl)hydroxylamine ((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate 、 3-苯丙酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以76%的产率得到(R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl 3-phenylpropanamide
  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：

  N-[1-(1'-naphthyl)ethyl]-O-tert-butylhydroxylamine 、 camphor-10-sulfonic acid 以 丙酮 为溶剂， 反应 12.0h， 以32.9 g的产率得到(S)-O-(tert-butyl)-N-(1-(naphthalen-1-yl)ethyl)hydroxylamine ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate
  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