(2R,5R)-5-<2'-(3''-Hydroxyphenyl)ethyl>proline tert-butyl ester | 1027488-63-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,5R)-5-<2'-(3''-Hydroxyphenyl)ethyl>proline tert-butyl ester
• 英文别名: tert-butyl (2R,5R)-5-[2-(3-hydroxyphenyl)ethyl]pyrrolidine-2-carboxylate
• CAS: 1027488-63-6
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: VUHVDYCGVZBXQV-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,5R)-5-<2'-(3''-Hydroxyphenyl)ethyl>proline tert-butyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 45.0 ℃ 、413.68 kPa 条件下， 反应 72.0h， 生成 (2R,5R,1''R/S,3''R/S)-5-<2'-(3''-Hydroxycyclohexyl)ethyl>proline tert-butyl ester 、 (2R,5R,1''R/S)-5-<2'-(3'',3''-Dimethoxycyclohexyl)ethyl>proline tert-butyl ester
  参考文献：
  名称：

  Conformationally Constrained Analogs of Anatoxin. Chirospecific Synthesis of s-Trans Carbonyl Ring-Fused Analogs

  摘要：

  Anatoxin is the most potent agonist known for the nicotinic acetylcholine receptor (nAChR). Although it possesses a semirigid structure, it can adopt four distinctly different conformations. Further conformationally constrained analogues of anatoxin should help to refine and discriminate among the current models for activation of this receptor. This report describes three s-trans ring-fused analogues which have been synthesized starting from D-glutamic acid and 3-hydroxyacetophenone. All of them have in common a 3-oxo-13-azatricyclo[8.2.1.0(2,7)]trideclane structure. They represent the first fully constrained analogues of anatoxin and are designed to serve as probes of the bioactive conformation of anatoxin at the acetylcholine nicotinic receptor site.

  DOI：

  10.1021/jo00084a023
• 作为产物：
  描述：

  3-苄氧基苯乙酮 在 palladium on activated charcoal 盐酸 、 乙酸异丙烯酯 、 氢气 、 pyridinium hydrobromide perbromide 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 112.2h， 生成 (2R,5R)-5-<2'-(3''-Hydroxyphenyl)ethyl>proline tert-butyl ester
  参考文献：
  名称：

  Conformationally Constrained Analogs of Anatoxin. Chirospecific Synthesis of s-Trans Carbonyl Ring-Fused Analogs

  摘要：

  Anatoxin is the most potent agonist known for the nicotinic acetylcholine receptor (nAChR). Although it possesses a semirigid structure, it can adopt four distinctly different conformations. Further conformationally constrained analogues of anatoxin should help to refine and discriminate among the current models for activation of this receptor. This report describes three s-trans ring-fused analogues which have been synthesized starting from D-glutamic acid and 3-hydroxyacetophenone. All of them have in common a 3-oxo-13-azatricyclo[8.2.1.0(2,7)]trideclane structure. They represent the first fully constrained analogues of anatoxin and are designed to serve as probes of the bioactive conformation of anatoxin at the acetylcholine nicotinic receptor site.

  DOI：

  10.1021/jo00084a023

文献信息

• Conformationally Constrained Analogs of Anatoxin. Chirospecific Synthesis of s-Trans Carbonyl Ring-Fused Analogs
  作者：Andres Hernandez、Henry Rapoport

  DOI：10.1021/jo00084a023

  日期：1994.3

  Anatoxin is the most potent agonist known for the nicotinic acetylcholine receptor (nAChR). Although it possesses a semirigid structure, it can adopt four distinctly different conformations. Further conformationally constrained analogues of anatoxin should help to refine and discriminate among the current models for activation of this receptor. This report describes three s-trans ring-fused analogues which have been synthesized starting from D-glutamic acid and 3-hydroxyacetophenone. All of them have in common a 3-oxo-13-azatricyclo[8.2.1.0(2,7)]trideclane structure. They represent the first fully constrained analogues of anatoxin and are designed to serve as probes of the bioactive conformation of anatoxin at the acetylcholine nicotinic receptor site.