(S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl propionate | 850452-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl propionate
• 英文别名: tert-butyl (3S)-3-(propanoyloxymethyl)piperidine-1-carboxylate
• CAS: 850452-56-1
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: KOSCCKXOYGPRRN-NSHDSACASA-N

物化性质

• 沸点：
  339.2±15.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl propionate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (S)-piperidin-3-ylmethyl propionate
  参考文献：
  名称：

  N-[¹⁸F]Fluoroethylpiperidin-4ylmethyl Acetate, a Novel Lipophilic Acetylcholine Analogue for PET Measurement of Brain Acetylcholinesterase Activity

  摘要：

  The reduction of acetylcholinesterase (AChE) activity in the brain has been measured in dementia disorders such as Alzheimer's disease and dementia with Lewy bodies using C-11-labeled acetylcholine analogues, N-[C-11]methylpiperidin-4-yl acetate and propionate, and positron emission tomography (PET). Our aim was to develop an F-18-labeled acetylcholine analogue useful for brain AChE mapping with PET, since F-18, with a longer half-life, has advantages over C-11. In a preliminary study, a series of N-[C-14]ethylpiperidin-3-yl or -4yl-methanol esters (acetyl and propionyl esters) were newly designed and evaluated in vitro regarding the reactivity with and specificity to AChE using purified human enzymes, leading to a novel F-18-labeled acetylcholine analogue, N-[F-18]fluoroethylpiperidin-4-ylmethyl acetate. In rat experiments, the F-18-labeled candidate showed desirable properties for PET AChE measurement: high brain uptake of the authentic ester, high AChE specificity, a moderate hydrolysis rate, and low membrane permeability (metabolic trapping) of the metabolite.

  DOI：

  10.1021/jm049100w
• 作为产物：
  描述：

  1-Boc-3-羟甲基哌啶 在 吡啶 、 sodium hydroxide 、 Lipase PS 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 7.0h， 生成 (S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl propionate
  参考文献：
  名称：

  N-[¹⁸F]Fluoroethylpiperidin-4ylmethyl Acetate, a Novel Lipophilic Acetylcholine Analogue for PET Measurement of Brain Acetylcholinesterase Activity

  摘要：

  The reduction of acetylcholinesterase (AChE) activity in the brain has been measured in dementia disorders such as Alzheimer's disease and dementia with Lewy bodies using C-11-labeled acetylcholine analogues, N-[C-11]methylpiperidin-4-yl acetate and propionate, and positron emission tomography (PET). Our aim was to develop an F-18-labeled acetylcholine analogue useful for brain AChE mapping with PET, since F-18, with a longer half-life, has advantages over C-11. In a preliminary study, a series of N-[C-14]ethylpiperidin-3-yl or -4yl-methanol esters (acetyl and propionyl esters) were newly designed and evaluated in vitro regarding the reactivity with and specificity to AChE using purified human enzymes, leading to a novel F-18-labeled acetylcholine analogue, N-[F-18]fluoroethylpiperidin-4-ylmethyl acetate. In rat experiments, the F-18-labeled candidate showed desirable properties for PET AChE measurement: high brain uptake of the authentic ester, high AChE specificity, a moderate hydrolysis rate, and low membrane permeability (metabolic trapping) of the metabolite.

  DOI：

  10.1021/jm049100w