[(R)-1-((1R,2S)-2-Diethylcarbamoyl-2-phenyl-cyclopropyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester | 213018-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(R)-1-((1R,2S)-2-Diethylcarbamoyl-2-phenyl-cyclopropyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R)-1-[(1R,2S)-2-(diethylcarbamoyl)-2-phenylcyclopropyl]-2-hydroxyethyl]carbamate
• CAS: 213018-90-7
• 化学式: C₂₁H₃₂N₂O₄
• 分子量: 376.496
• InChiKey: ZLZPYSCHMDAVCB-XGHQBKJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(R)-1-((1R,2S)-2-Diethylcarbamoyl-2-phenyl-cyclopropyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester 在 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 5.0h， 生成 tert-butyl N-[(1S)-1-[(1R,2S)-2-(diethylcarbamoyl)-2-phenylcyclopropyl]prop-2-enyl]carbamate
  参考文献：
  名称：

  Synthesis and Biological Activity of Conformationally Restricted Analogues of Milnacipran:  (1S,2R)-1-Phenyl-2-[(R)-1-amino-2-propynyl]-N,N- diethylcyclopropanecarboxamide Is a Novel Class of NMDA Receptor Channel Blocker

  摘要：

  Conformationally restricted analogues of (+/-)-(Z)-2-aminomethyl-1-phenyl-N, N-diethylcyclopropanecarboxamide [milnacipran, (+/-)-1] were designed on the basis of its characteristic cyclopropane structure and were synthesized enantioselectively to develop efficient NMDA receptor antagonists. Among these analogues, (1S,2R)-1-phenyl-2-[(R)-1-amino-2-propynyl]- N,N-diethylcyclopropanecarboxamide (2d) had one of the most potent affinities for the receptor, with a K-i value of 0.29 mu M. The blockade of NMDA receptor channels expressed by Xenopus oocytes by 2d was investigated in detail, and 2d was identified as a new class of open channel blocker against this receptor.

  DOI：

  10.1021/jm980238m
• 作为产物：
  描述：

  (1S,2R)-2-((R)-Amino-cyano-methyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide; hydrochloride 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 17.5h， 生成 [(R)-1-((1R,2S)-2-Diethylcarbamoyl-2-phenyl-cyclopropyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Biological Activity of Conformationally Restricted Analogues of Milnacipran:  (1S,2R)-1-Phenyl-2-[(R)-1-amino-2-propynyl]-N,N- diethylcyclopropanecarboxamide Is a Novel Class of NMDA Receptor Channel Blocker

  摘要：

  Conformationally restricted analogues of (+/-)-(Z)-2-aminomethyl-1-phenyl-N, N-diethylcyclopropanecarboxamide [milnacipran, (+/-)-1] were designed on the basis of its characteristic cyclopropane structure and were synthesized enantioselectively to develop efficient NMDA receptor antagonists. Among these analogues, (1S,2R)-1-phenyl-2-[(R)-1-amino-2-propynyl]- N,N-diethylcyclopropanecarboxamide (2d) had one of the most potent affinities for the receptor, with a K-i value of 0.29 mu M. The blockade of NMDA receptor channels expressed by Xenopus oocytes by 2d was investigated in detail, and 2d was identified as a new class of open channel blocker against this receptor.

  DOI：

  10.1021/jm980238m