N,N-diisopropyl-8-(tert-butyldimethylsilyloxy)-2-hydroxy-1-naphthamide | 676566-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-diisopropyl-8-(tert-butyldimethylsilyloxy)-2-hydroxy-1-naphthamide
• 英文别名: 8-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 676566-15-7
• 化学式: C₂₃H₃₅NO₃Si
• 分子量: 401.621
• InChiKey: RZNUMPYSUNVREI-UHFFFAOYSA-N

物化性质

• 沸点：
  497.6±30.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diisopropyl-8-(tert-butyldimethylsilyloxy)-2-hydroxy-1-naphthamide 在 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (+)-(aS,1'S,4'R)-N,N-diisopropyl-8-methoxy-2-{4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo[2.2.1]heptanecarbonyloxy}-1-naphthamide
  参考文献：
  名称：

  Synthesis of atropisomeric 2,8-dioxygenated N,N-diisopropyl-1-naphthamides via kinetic resolution under Sharpless asymmetric dihydroxylation conditions

  摘要：

  A kinetic resolution approach under Sharpless asymmetric dihydroxylation conditions was used to synthesize enantio-enriched atropisomeric N,N-diisopropyl-1-naphthamides possessing oxygenated functionalities at both the C2 and C8 positions. A significant influence of the substrate structures on the efficiency of the kinetic resolution was observed. (+)-(aS)-N,N-Diisopropyl-2[2'-(E)-butenoyloxy]-8-methoxy-1-naphthamide is obtained in 35% yield with 94.3% ee after treating the racemate with 3.5 mol% each of Os and (DHQD)(2)-PHAL at 0degreesC for 22 h. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.039
• 作为产物：
  描述：

  N,N-diisopropyl-8-hydroxy-1-naphthamide 在 咪唑 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 N,N-diisopropyl-8-(tert-butyldimethylsilyloxy)-2-hydroxy-1-naphthamide
  参考文献：
  名称：

  Synthesis of atropisomeric 2,8-dioxygenated N,N-diisopropyl-1-naphthamides via kinetic resolution under Sharpless asymmetric dihydroxylation conditions

  摘要：

  A kinetic resolution approach under Sharpless asymmetric dihydroxylation conditions was used to synthesize enantio-enriched atropisomeric N,N-diisopropyl-1-naphthamides possessing oxygenated functionalities at both the C2 and C8 positions. A significant influence of the substrate structures on the efficiency of the kinetic resolution was observed. (+)-(aS)-N,N-Diisopropyl-2[2'-(E)-butenoyloxy]-8-methoxy-1-naphthamide is obtained in 35% yield with 94.3% ee after treating the racemate with 3.5 mol% each of Os and (DHQD)(2)-PHAL at 0degreesC for 22 h. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.039

文献信息

• Synthesis of atropisomeric 2,8-dioxygenated N,N-diisopropyl-1-naphthamides via kinetic resolution under Sharpless asymmetric dihydroxylation conditions
  作者：Wei-Min Dai、Yan Zhang、Ye Zhang

  DOI：10.1016/j.tetasy.2003.11.039

  日期：2004.2

  A kinetic resolution approach under Sharpless asymmetric dihydroxylation conditions was used to synthesize enantio-enriched atropisomeric N,N-diisopropyl-1-naphthamides possessing oxygenated functionalities at both the C2 and C8 positions. A significant influence of the substrate structures on the efficiency of the kinetic resolution was observed. (+)-(aS)-N,N-Diisopropyl-2[2'-(E)-butenoyloxy]-8-methoxy-1-naphthamide is obtained in 35% yield with 94.3% ee after treating the racemate with 3.5 mol% each of Os and (DHQD)(2)-PHAL at 0degreesC for 22 h. (C) 2003 Elsevier Ltd. All rights reserved.