1,4-Ethano-2-oxo-N-ω-undecenyl-1,2,3,4-tetrahydronaphthalene-9,10-endo-dicarboximide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,4-Ethano-2-oxo-N-ω-undecenyl-1,2,3,4-tetrahydronaphthalene-9,10-endo-dicarboximide
• 英文别名: (1S,8R,9R,13S)-11-undec-10-enyl-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-10,12,14-trione
• 化学式: C₂₅H₃₁NO₃
• 分子量: 393.526
• InChiKey: GFIZVJLBLOROOQ-SNJCGAMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-Ethano-2-oxo-N-ω-undecenyl-1,2,3,4-tetrahydronaphthalene-9,10-endo-dicarboximide 在 ammonium acetate 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 (1R,2R,4S,9R,10S)-(+)-1,4-Ethano-2-endo-(3,5-dinitrobenzamido)-N-ω-undecenyl-1,2,3,4-tetrahydronaphthalene-9,10-endo-dicarboximide
  参考文献：
  名称：

  Design, Synthesis, Resolution, Determination of Absolute Configuration, and Evaluation of a Chiral Naproxen Selector

  摘要：

  A rigid chiral selector intended to differentiate between the enantiomers of alpha-arylpropionic acids (profens) has been designed and synthesized. The pi-acidic, hydrogen bond donor, and pi-basic interaction sites deemed essential to chiral recognition are supported on a [2.2.2]bicyclooctane framework to form a cleft-like ''active site'' in which enantiodiscrimination occurs. The racemic selector has been resolved chromatographically and the absolute configurations of the enantiomers have been established by a combination of HPLC and NMR methods. Immobilized on silica, this selector affords a chiral stationary phase which shows appreciable levels of enantioselectivity toward the profens, members of an important group of nonsteroidal antiinflammatory drugs. Immobilization has been accomplished in two ways. The selector has been hydrosilylated with either dimethylchlorosilane or with polymethylhydrosiloxane. The former leads to a brush-type CSP whereas the latter leads to a polymeric CSP coated and bonded to the silica support. The polysiloxane-based phase exhibits higher enantioselectivity and shorter retention times than does its brush-type counterpart. A mechanistic hypothesis advanced to account for the enantiodiscrimination observed suggests that relatively simple changes in the structure of the selector might further improve its enantioselectivity.

  DOI：

  10.1021/jo00102a013
• 作为产物：
  描述：

  undec-10-enamide 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 28.0h， 生成 1,4-Ethano-2-oxo-N-ω-undecenyl-1,2,3,4-tetrahydronaphthalene-9,10-endo-dicarboximide
  参考文献：
  名称：

  Design, Synthesis, Resolution, Determination of Absolute Configuration, and Evaluation of a Chiral Naproxen Selector

  摘要：

  A rigid chiral selector intended to differentiate between the enantiomers of alpha-arylpropionic acids (profens) has been designed and synthesized. The pi-acidic, hydrogen bond donor, and pi-basic interaction sites deemed essential to chiral recognition are supported on a [2.2.2]bicyclooctane framework to form a cleft-like ''active site'' in which enantiodiscrimination occurs. The racemic selector has been resolved chromatographically and the absolute configurations of the enantiomers have been established by a combination of HPLC and NMR methods. Immobilized on silica, this selector affords a chiral stationary phase which shows appreciable levels of enantioselectivity toward the profens, members of an important group of nonsteroidal antiinflammatory drugs. Immobilization has been accomplished in two ways. The selector has been hydrosilylated with either dimethylchlorosilane or with polymethylhydrosiloxane. The former leads to a brush-type CSP whereas the latter leads to a polymeric CSP coated and bonded to the silica support. The polysiloxane-based phase exhibits higher enantioselectivity and shorter retention times than does its brush-type counterpart. A mechanistic hypothesis advanced to account for the enantiodiscrimination observed suggests that relatively simple changes in the structure of the selector might further improve its enantioselectivity.

  DOI：

  10.1021/jo00102a013

文献信息

• Design, Synthesis, Resolution, Determination of Absolute Configuration, and Evaluation of a Chiral Naproxen Selector
  作者：William H. Pirkle、Yuelong Liu

  DOI：10.1021/jo00102a013

  日期：1994.11

  A rigid chiral selector intended to differentiate between the enantiomers of alpha-arylpropionic acids (profens) has been designed and synthesized. The pi-acidic, hydrogen bond donor, and pi-basic interaction sites deemed essential to chiral recognition are supported on a [2.2.2]bicyclooctane framework to form a cleft-like ''active site'' in which enantiodiscrimination occurs. The racemic selector has been resolved chromatographically and the absolute configurations of the enantiomers have been established by a combination of HPLC and NMR methods. Immobilized on silica, this selector affords a chiral stationary phase which shows appreciable levels of enantioselectivity toward the profens, members of an important group of nonsteroidal antiinflammatory drugs. Immobilization has been accomplished in two ways. The selector has been hydrosilylated with either dimethylchlorosilane or with polymethylhydrosiloxane. The former leads to a brush-type CSP whereas the latter leads to a polymeric CSP coated and bonded to the silica support. The polysiloxane-based phase exhibits higher enantioselectivity and shorter retention times than does its brush-type counterpart. A mechanistic hypothesis advanced to account for the enantiodiscrimination observed suggests that relatively simple changes in the structure of the selector might further improve its enantioselectivity.