(+/-)-threo-N-methyl methyl phenyl(piperidine-2-yl)acetate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-threo-N-methyl methyl phenyl(piperidine-2-yl)acetate
• 英文别名: (+/-)-threo-N-methyl methyl phenyl(piperidin-2-yl)acetate；(R)-((R)-1-Methyl-piperidin-2-yl)-phenyl-acetic acid methyl ester；methyl (2R)-2-[(2R)-1-methylpiperidin-2-yl]-2-phenylacetate
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: ZMWIDYCUFHNGLQ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-threo-N-methyl methyl phenyl(piperidine-2-yl)acetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.33h， 以96%的产率得到(+/-)-threo-N-methyl ritalinol
  参考文献：
  名称：

  (±)-苏-甲基苯基(哌啶-2-基)乙酸酯新系列哌啶环改性醇和甲基醚类似物的有效合成

  摘要：

  摘要 合成了一系列新型哌啶环改性醇和(±)-苏-甲基苯基(哌啶-2-基)乙酸酯的甲基醚类似物。该系列甲基苯基(哌啶-2-基)乙酸酯类似物是通过哌啶环烷基化和/或酰化，然后氢化铝锂还原得到醇衍生物而开发的。通过扩展标准文献程序对醇类似物进行甲基化得到相应的甲基醚衍生物。这些化合物的化学结构是根据质量和 1H NMR 光谱数据以及 CHN 元素分析数据确定的。对文献方法的一些重大修改使反应更有效，并且通常获得了良好的产率。图形概要

  DOI：

  10.1080/00397911.2011.569681
• 作为产物：
  描述：

  聚合甲醛 、 盐酸右哌甲酯 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以80%的产率得到(+/-)-threo-N-methyl methyl phenyl(piperidine-2-yl)acetate
  参考文献：
  名称：

  Further evidence for a dopamine reuptake pharmacophore. The effect of N-methylation on Threo-methylphenidate and its analogs

  摘要：

  N-methyl derivatives of methylphenidate and four analogs were synthesized and assayed for affinity at the dopamine transporter. The binding affinities of the N-methyl compounds were consistently lower by a factor ranging from 4 to 30 as compared with the corresponding secondary amine. This is consistent with the predictions of a pharmacophore model of compounds that bind to the dopamine transporter. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00193-5

文献信息

• Reversal of general anesthesia by administration of methylphenidate, amphetamine, modafinil, amantadine, and/or caffeine
  申请人：The General Hospital Corporation

  公开号：US10299720B2

  公开（公告）日：2019-05-28

  The present invention generally relates to compositions comprising anesthesia-reversing agents which facilitate or increase the time of awakening or reverse the effects of general anesthesia-induced unconsciousness. In some embodiments, the anesthesia reversing agent can be selected from any or a combination of methylphenidate (MPH), amphetamine, modafinil, amantadine, caffeine, or analogs or derivatives thereof. In some embodiments, compositions comprising at least one or more anesthesia-reversing agents can be used to facilitate awakening from anesthesia without or decreasing occurrence of delirium, and can be used in methods to treat or prevent the symptoms associated with emergence delirium, as well as treat a subject oversedated with general an esthesia. The invention also relates to methods for administering these compositions comprising anesthesia-reversing agents to subjects and for use.

  本发明一般涉及包含麻醉逆转剂的组合物，该组合物可促进或增加苏醒时间或逆转全身麻醉引起的昏迷的影响。在一些实施方案中，麻醉逆转剂可以选自哌醋甲酯（MPH）、苯丙胺、莫达非尼、金刚烷胺、咖啡因或其类似物或衍生物中的任何一种或其组合。在一些实施方案中，包含至少一种或多种麻醉逆转剂的组合物可用于促进麻醉苏醒，而不会或减少谵妄的发生，并可用于治疗或预防与出现谵妄相关的症状的方法，以及治疗全身麻醉过度兴奋的受试者。本发明还涉及向受试者施用这些包含麻醉逆转剂的组合物的方法和用途。
• Efficient Synthesis of a New Series of Piperidine Ring-Modified Analogs of (±)-<i>threo</i>-Methyl Phenyl(piperidin-2-yl)acetate
  作者：Babatunde Ojo

  DOI：10.1080/00397911.2010.543305

  日期：2012.6.15

  A series of novel piperidine ring modified analogs of (+/-)-threo-methyl phenyl (piperidin-2-yl)acetate was synthesized by direct alkylation and reductive amination procedure, using sodium borohydride over molecular sieves. The chemical structures of these compounds were established based on mass spectra, H-1 NMR spectra, and CHN elemental analysis data. Several significant modifications in the literature methodologies were made to make the reaction more efficient, and good yields were generally obtained.
• Reversal of General Anesthesia by Administration of Methylphenidate, Amphetamine, Modafinil, Amantadine, and/or Caffeine
  申请人：The General Hospital Corporation

  公开号：US20200029892A1

  公开（公告）日：2020-01-30

  The present invention generally relates to compositions comprising anesthesia-reversing agents which facilitate or increase the time of awakening or reverse the effects of general anesthesia-induced unconsciousness. In some embodiments, the anesthesia reversing agent can be selected from any or a combination of methylphenidate (MPH), amphetamine, modafinil, amantadine, caffeine, or analogues or derivatives thereof. In some embodiments, compositions comprising at least one or more anesthesia-reversing agents can be used to facilitate awakening from anesthesia without or decreasing occurrence of delirium, and can be used in methods to treat or prevent the symptoms associated with emergence delirium, as well as treat a subject oversedated with general anesthesia. The invention also relates to methods for administering these compositions comprising anesthesia-reversing agents to subjects and for use.
• Further evidence for a dopamine reuptake pharmacophore. The effect of N-methylation on Threo-methylphenidate and its analogs
  作者：Mark Froimowitz、Howard M. Deutsh、Quing Shi、Kuo-Ming Wu、Robert Glaser、Itay Adin、Clifford George、Margaret M. Schweri

  DOI：10.1016/s0960-894x(97)00193-5

  日期：1997.5

  N-methyl derivatives of methylphenidate and four analogs were synthesized and assayed for affinity at the dopamine transporter. The binding affinities of the N-methyl compounds were consistently lower by a factor ranging from 4 to 30 as compared with the corresponding secondary amine. This is consistent with the predictions of a pharmacophore model of compounds that bind to the dopamine transporter. (C) 1997 Elsevier Science Ltd.
• Efficient Synthesis of a New Series of Piperidine Ring–Modified Alcohol and Methyl Ether Analogs of (±)-<i>threo</i>-Methyl Phenyl(piperidin-2-yl)acetate
  作者：Babatunde Ojo

  DOI：10.1080/00397911.2011.569681

  日期：2012.10

  Abstract A series of novel piperidine ring–modified alcohol and methyl ether analogs of (±)-threo-methyl phenyl(piperidin-2-yl)acetate was synthesized. This series of methyl phenyl(piperidin-2-yl)acetate analogs was developed by piperidine ring alkylation and/or acylation followed by lithium aluminum hydride reduction to give alcohol derivatives. Methylation of the alcohol analogs by extension of standard

  摘要 合成了一系列新型哌啶环改性醇和(±)-苏-甲基苯基(哌啶-2-基)乙酸酯的甲基醚类似物。该系列甲基苯基(哌啶-2-基)乙酸酯类似物是通过哌啶环烷基化和/或酰化，然后氢化铝锂还原得到醇衍生物而开发的。通过扩展标准文献程序对醇类似物进行甲基化得到相应的甲基醚衍生物。这些化合物的化学结构是根据质量和 1H NMR 光谱数据以及 CHN 元素分析数据确定的。对文献方法的一些重大修改使反应更有效，并且通常获得了良好的产率。图形概要