(1S,2R)-1-phenyl-2-[(S)-1-hydroxypropyl]-N,N-dipropylcyclopropanecarboxamide | 459143-46-5

• 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: (1S,2R)-1-phenyl-2-[(S)-1-hydroxypropyl]-N,N-dipropylcyclopropanecarboxamide
• CAS: 459143-46-5
• 化学式: C₁₉H₂₉NO₂
• 分子量: 303.445
• InChiKey: DQFIZNIZIYQBMK-JENIJYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-phenyl-2-[(S)-1-hydroxypropyl]-N,N-dipropylcyclopropanecarboxamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以61%的产率得到(1S,4S,5R)-2-oxo-4-ethyl-1-phenyl-3-oxabicyclo[3.1.0]hexane
  参考文献：
  名称：

  Synthesis of (1S,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC) Derivatives Modified at the Carbamoyl Moiety As a New Class of NMDA Receptor Antagonists

  摘要：

  (IS,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC, 4a), which is a conformationally restricted analogue of the antidepressant milnacipran [(+/-)-1], represents a new class of potent NMDA receptor antagonists. A series of PPDC analogues modified at the carbamoyl moiety were synthesized. Among these, (IS,2R)-l-phenyl-2-[(S)-l-aminopropyl]-N,N-dipropylcyclopropanecarboxamide (4d) was identified as the most potent NMDA receptor antagonist in this series and clearly reduced the MMDA receptor mediated potentiation of rat hippocampal slices, a model of long-term potentiation (LTP). The three-dimensional structure of 4d was also analyzed in detail to clarify the receptor-binding conformation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00030-5
• 作为产物：
  描述：

  二正丙胺 在 三氯化铝 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (1S,2R)-1-phenyl-2-[(S)-1-hydroxypropyl]-N,N-dipropylcyclopropanecarboxamide
  参考文献：
  名称：

  Synthesis of (1S,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC) Derivatives Modified at the Carbamoyl Moiety As a New Class of NMDA Receptor Antagonists

  摘要：

  (IS,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC, 4a), which is a conformationally restricted analogue of the antidepressant milnacipran [(+/-)-1], represents a new class of potent NMDA receptor antagonists. A series of PPDC analogues modified at the carbamoyl moiety were synthesized. Among these, (IS,2R)-l-phenyl-2-[(S)-l-aminopropyl]-N,N-dipropylcyclopropanecarboxamide (4d) was identified as the most potent NMDA receptor antagonist in this series and clearly reduced the MMDA receptor mediated potentiation of rat hippocampal slices, a model of long-term potentiation (LTP). The three-dimensional structure of 4d was also analyzed in detail to clarify the receptor-binding conformation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00030-5