1-(tert-butyloxycarbonyl)-4-[(3-(pyridin-4-yl)phenyl)methyl]-piperazine | 1043508-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(tert-butyloxycarbonyl)-4-[(3-(pyridin-4-yl)phenyl)methyl]-piperazine
• 英文别名: tert-butyl 4-(3-(pyridin-4-yl)benzyl)piperazine-1-carboxylate；tert-butyl 4-[(3-pyridin-4-ylphenyl)methyl]piperazine-1-carboxylate
• CAS: 1043508-39-9
• 化学式: C₂₁H₂₇N₃O₂
• 分子量: 353.464
• InChiKey: ZNORULVOIWERIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.67
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(tert-butyloxycarbonyl)-4-[(3-(pyridin-4-yl)phenyl)methyl]-piperazine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以97%的产率得到N-[(3-(pyridin-4-yl)phenyl)methyl]-piperazine
  参考文献：
  名称：

  Design and evaluation of a novel series of 2,3-oxidosqualene cyclase inhibitors with low systemic exposure, relationship between pharmacokinetic properties and ocular toxicity

  摘要：

  We describe the discovery of novel potent inhibitors of 2,3-oxidosqualene: lanosterol cyclase inhibitors (OSCi) from a focused pharmacophore-based screen. Optimization of the most tractable hits gave a series of compounds showing inhibition of cholesterol biosynthesis at 2 mg/kg in the rat with distinct pharmacokinetic profiles. Two compounds were selected for toxicological study in the rat for 21 days in order to test the hypothesis that low systemic exposure could be used as a strategy to avoid the ocular side effects previously described with OSCi. We demonstrate that for this series of inhibitors, a reduction of systemic exposure is not sufficient to circumvent cataract liabilities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.034
• 作为产物：
  描述：

  3-甲酰基苯硼酸 在 palladium diacetate 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 生成 1-(tert-butyloxycarbonyl)-4-[(3-(pyridin-4-yl)phenyl)methyl]-piperazine
  参考文献：
  名称：

  通过N至C转换从吡啶合成苯

  摘要：

  杂芳烃的骨架编辑为化学词典引入了新的断开，通过选择性破坏/重建碳框架实现环系统的相互转换。我们描述了使用软亲核试剂（例如丙二酸）的亲核加成开环/闭环（ANRORC）过程将吡啶一锅转化为苯衍生物。三氟甲磺酸酐通过可分离的胺中间体激活吡啶进行 ANRORC 合成，该中间体在简单加热下芳构化。该反应已通过室温方案以及药物样、叔烷基化和同位素标记苯甲酸酯的直接合成进行了举例说明。

  DOI：

  10.1016/j.chempr.2024.05.004

文献信息

• Design and evaluation of a novel series of 2,3-oxidosqualene cyclase inhibitors with low systemic exposure, relationship between pharmacokinetic properties and ocular toxicity
  作者：Marie-Hélène Fouchet、Frédéric Donche、Christelle Martin、Anne Bouillot、Christophe Junot、Anne-Bénédicte Boullay、Florent Potvain、Sylvie Demaria Magny、Hervé Coste、Max Walker、Marc Issandou、Nérina Dodic

  DOI：10.1016/j.bmc.2008.04.034

  日期：2008.6

  We describe the discovery of novel potent inhibitors of 2,3-oxidosqualene: lanosterol cyclase inhibitors (OSCi) from a focused pharmacophore-based screen. Optimization of the most tractable hits gave a series of compounds showing inhibition of cholesterol biosynthesis at 2 mg/kg in the rat with distinct pharmacokinetic profiles. Two compounds were selected for toxicological study in the rat for 21 days in order to test the hypothesis that low systemic exposure could be used as a strategy to avoid the ocular side effects previously described with OSCi. We demonstrate that for this series of inhibitors, a reduction of systemic exposure is not sufficient to circumvent cataract liabilities. (C) 2008 Elsevier Ltd. All rights reserved.
• 10.1016/j.chempr.2024.05.004
  作者：Conboy, Aífe、Greaney, Michael F.

  DOI：10.1016/j.chempr.2024.05.004

  日期：——

  introduces new disconnections to the chemistry lexicon, enabling the interconversion of ring systems via selective breaking/re-making of the carbon framework. We describe the one-pot transformation of pyridines into benzene derivatives, using a nucleophilic addition ring-opening/ring-closing (ANRORC) process with soft nucleophiles such as malonate. Triflic anhydride activates the pyridine to ANRORC synthesis

  杂芳烃的骨架编辑为化学词典引入了新的断开，通过选择性破坏/重建碳框架实现环系统的相互转换。我们描述了使用软亲核试剂（例如丙二酸）的亲核加成开环/闭环（ANRORC）过程将吡啶一锅转化为苯衍生物。三氟甲磺酸酐通过可分离的胺中间体激活吡啶进行 ANRORC 合成，该中间体在简单加热下芳构化。该反应已通过室温方案以及药物样、叔烷基化和同位素标记苯甲酸酯的直接合成进行了举例说明。