(1S,2R)-1-phenyl-2-formyl-N,N-dipropylcyclopropanecarboxamide | 459143-38-5

• 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-formyl-N,N-dipropylcyclopropanecarboxamide
• CAS: 459143-38-5
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: WKXJLPZSUVLJPJ-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-phenyl-2-formyl-N,N-dipropylcyclopropanecarboxamide 在 palladium on activated charcoal 四溴化碳 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 为溶剂， 反应 27.5h， 生成 (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-dipropylcyclopropanecarboxamide hydrochloride
  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 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1S,2R)-1-phenyl-2-formyl-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