(S)-3-(1-benzylpiperazin-2-yl)propan-1-ol | 433285-25-7

• 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: (S)-3-(1-benzylpiperazin-2-yl)propan-1-ol
• 英文别名: 3-[(2S)-1-benzylpiperazin-2-yl]propan-1-ol
• CAS: 433285-25-7
• 化学式: C₁₄H₂₂N₂O
• 分子量: 234.341
• InChiKey: OZWKIFSLFPQPBF-AWEZNQCLSA-N

物化性质

• 沸点：
  367.0±22.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (S)-3-(1-benzylpiperazin-2-yl)propan-1-ol 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以59%的产率得到tert-butyl (S)-4-benzyl-3-(3-hydroxypropyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives

  摘要：

  Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxo-piperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of Ne-benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for sigma(1)-receptors (K-i=66.1 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01212-1
• 作为产物：
  描述：

  L-谷氨酸 在 palladium on activated charcoal sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium azide 、 氢气 、 sodium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 正戊烷 为溶剂， 66.0 ℃ 、101.3 kPa 条件下， 反应 73.17h， 生成 (S)-3-(1-benzylpiperazin-2-yl)propan-1-ol
  参考文献：
  名称：

  Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives

  摘要：

  Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxo-piperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of Ne-benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for sigma(1)-receptors (K-i=66.1 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01212-1

文献信息

• Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives
  作者：Manuela Weigl、Bernhard Wünsch

  DOI：10.1016/s0040-4020(01)01212-1

  日期：2002.2

  Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxo-piperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of Ne-benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for sigma(1)-receptors (K-i=66.1 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.