tert-butyl (S)-4-benzyl-3-(3-hydroxypropyl)piperazine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl (S)-4-benzyl-3-(3-hydroxypropyl)piperazine-1-carboxylate
• 英文别名: tert-butyl (3S)-4-benzyl-3-(3-hydroxypropyl)piperazine-1-carboxylate
• 化学式: C₁₉H₃₀N₂O₃
• 分子量: 334.459
• InChiKey: AEZOLAAHPJDDSF-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-谷氨酸 在 palladium on activated charcoal sodium hydroxide 、 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 、 水 、 丙酮 、 正戊烷 为溶剂， 66.0 ℃ 、101.3 kPa 条件下， 反应 89.17h， 生成 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

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.