(S)-naproxen undec-10-en-1-yl ester | 142634-66-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-naproxen undec-10-en-1-yl ester
• 英文别名: undec-10-enyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
• CAS: 142634-66-0
• 化学式: C₂₅H₃₄O₃
• 分子量: 382.543
• InChiKey: XUMPUEXJUTUDJA-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二甲基一氯硅烷 、 乙醇 、 (S)-naproxen undec-10-en-1-yl ester 在 dihydrogen hexachloroplatinate 三乙胺 作用下， 生成 (S)-10-(dimethylethoxysilyl)undecyl naproxenate
  参考文献：
  名称：

  Design, synthesis, and evaluation of an improved enantioselective naproxen selector

  摘要：

  The design, synthesis, and evaluation of an improved selector for the enantiomers of the nonsteroidal anti-inflammatory drug, naproxen, are described. So as to utilize the principle of reciprocity, two chiral stationary phases (CSPs) derived from (S)-naproxen were produced and HPLC techniques were used to screen candidate naproxen selectors. By determining how the structural features of the candidates influence enantioselective recognition by naproxen, a hypothetical chiral recognition mechanism for enantioselective recognition of naproxen was developed and used to design a selector which was incorporated into a new CSP. This comparatively simple CSP shows significant improvement in the separation of underivatized naproxen enantiomers relative to previous methods. Related compounds such as ibuprofen, ketoprofen, cicloprofen, fenoprofen, etc. are also resolved into their component enantiomers by this CSP.

  DOI：

  10.1021/jo00040a026
• 作为产物：
  描述：

  10-十一烯-1-醇 、 萘普生 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以99%的产率得到(S)-naproxen undec-10-en-1-yl ester
  参考文献：
  名称：

  Design, synthesis, and evaluation of an improved enantioselective naproxen selector

  摘要：

  The design, synthesis, and evaluation of an improved selector for the enantiomers of the nonsteroidal anti-inflammatory drug, naproxen, are described. So as to utilize the principle of reciprocity, two chiral stationary phases (CSPs) derived from (S)-naproxen were produced and HPLC techniques were used to screen candidate naproxen selectors. By determining how the structural features of the candidates influence enantioselective recognition by naproxen, a hypothetical chiral recognition mechanism for enantioselective recognition of naproxen was developed and used to design a selector which was incorporated into a new CSP. This comparatively simple CSP shows significant improvement in the separation of underivatized naproxen enantiomers relative to previous methods. Related compounds such as ibuprofen, ketoprofen, cicloprofen, fenoprofen, etc. are also resolved into their component enantiomers by this CSP.

  DOI：

  10.1021/jo00040a026

文献信息

• Design, synthesis, and evaluation of an improved enantioselective naproxen selector
  作者：William H. Pirkle、Christopher J. Welch、Bo Lamm

  DOI：10.1021/jo00040a026

  日期：1992.7

  The design, synthesis, and evaluation of an improved selector for the enantiomers of the nonsteroidal anti-inflammatory drug, naproxen, are described. So as to utilize the principle of reciprocity, two chiral stationary phases (CSPs) derived from (S)-naproxen were produced and HPLC techniques were used to screen candidate naproxen selectors. By determining how the structural features of the candidates influence enantioselective recognition by naproxen, a hypothetical chiral recognition mechanism for enantioselective recognition of naproxen was developed and used to design a selector which was incorporated into a new CSP. This comparatively simple CSP shows significant improvement in the separation of underivatized naproxen enantiomers relative to previous methods. Related compounds such as ibuprofen, ketoprofen, cicloprofen, fenoprofen, etc. are also resolved into their component enantiomers by this CSP.