4-amino-3-undec-10-en-1-yl-1,2,3,4-tetrahydrophenanthrene | 142634-69-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4-amino-3-undec-10-en-1-yl-1,2,3,4-tetrahydrophenanthrene
• 英文别名: 3-Undec-10-enyl-1,2,3,4-tetrahydrophenanthren-4-amine
• CAS: 142634-69-3；142634-70-6
• 化学式: C₂₅H₃₅N
• 分子量: 349.56
• InChiKey: GTWQQUXTTZRPCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-amino-3-undec-10-en-1-yl-1,2,3,4-tetrahydrophenanthrene 在 dihydrogen hexachloroplatinate 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-[(3R,4R)-3-[11-[ethoxy(dimethyl)silyl]undecyl]-1,2,3,4-tetrahydrophenanthren-4-yl]-3,5-dinitrobenzamide
  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 在 乙酸铵 、 二环己烷并-18-冠醚-6 、 potassium tert-butylate 、 sodium cyanoborohydride 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 水 、 异丙醇 、 苯 为溶剂， 反应 31.75h， 生成 4-amino-3-undec-10-en-1-yl-1,2,3,4-tetrahydrophenanthrene
  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

• US5256293A
  申请人：——

  公开号：US5256293A

  公开（公告）日：1993-10-26
• US5387338A
  申请人：——

  公开号：US5387338A

  公开（公告）日：1995-02-07
• US5484530A
  申请人：——

  公开号：US5484530A

  公开（公告）日：1996-01-16
• US5674387A
  申请人：——

  公开号：US5674387A

  公开（公告）日：1997-10-07
• [EN] SEPARATION OF ENANTIOMERS OF NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND CHIRAL SELECTOR THEREFOR
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：WO1993006080A1

  公开（公告）日：1993-04-01

  (EN) The invention relates to a chiral selector useful in separating underivatized enantiomers of non-steroidal anti-inflammatory agents, particularly naproxen and other arylacetic acid compounds, and relates to a process for achieving such separation utilizing the chiral selector, which is also useful in achieving the enantiomeric separation of amines, alcohol derivatives, epoxides and sulfoxides. The invention is also directed to an apparatus which comprises the chiral selectors.(FR) Sélecteur chiral utile dans la séparation d'énantiomères non dérivés d'agents anti-inflammatoires non stéroidiens, notamment du naproxène et d'autres composés de l'acide arylacétique. L'invention décrit aussi un procédé permettant d'effectuer cette séparation en utilisant le sélecteur chiral, ce procédé étant également utile dans la séparation énantiomère d'amines, de dérivés d'alcool, d'époxydes et de sulfoxydes. L'invention se rapporte également à un appareil comprenant les sélecteurs chiraux.