N,N-dibenzyl-2-phenylcyclopropanamine | 220247-82-5

• 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: N,N-dibenzyl-2-phenylcyclopropanamine
• 英文别名: N,N-dibenzyl-N-(2-phenylcyclopropyl)-amine；(Z)-N,N-dibenzyl-(2-phenylcyclopropyl)-amine；N,N-dibenzyl-2-phenylcyclopropan-1-amine
• CAS: 220247-82-5
• 化学式: C₂₃H₂₃N
• 分子量: 313.442
• InChiKey: NGAFEPCWKQXDCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyl-2-phenylcyclopropanamine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 2-苯基环丙胺
  参考文献：
  名称：

  The Kulinkovich Reaction in the Synthesis of Constrained N,N-Dialkyl Neurotransmitter Analogues

  摘要：

  An intermolecular Ti(IV)-mediated cyclopropanation reaction has been used to synthesize substituted 2-phenylcyclopropylamines and constrained analogues of the neurotransmitters histamine and tryptamine. Many hydroxy- and methoxy-substituted phenylcyclopropylamines are known to inhibit monoamine oxidase and have been shown to mimic hallucinogens. These compounds were made in 1 to 5 steps from readily available starting materials.

  DOI：

  10.1021/ol0705907
• 作为产物：
  描述：

  苯乙烯 、 N,N-二苄基甲酰胺 在 三异丙氧基氯化钛 、 环戊基溴化镁 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到N,N-dibenzyl-2-phenylcyclopropanamine
  参考文献：
  名称：

  The Kulinkovich Reaction in the Synthesis of Constrained N,N-Dialkyl Neurotransmitter Analogues

  摘要：

  An intermolecular Ti(IV)-mediated cyclopropanation reaction has been used to synthesize substituted 2-phenylcyclopropylamines and constrained analogues of the neurotransmitters histamine and tryptamine. Many hydroxy- and methoxy-substituted phenylcyclopropylamines are known to inhibit monoamine oxidase and have been shown to mimic hallucinogens. These compounds were made in 1 to 5 steps from readily available starting materials.

  DOI：

  10.1021/ol0705907

文献信息

• VERFAHREN ZUR HERSTELLUNG VON CYCLOPROPYLAMINEN
  申请人：BAYER AG

  公开号：EP0938466A1

  公开（公告）日：1999-09-01
• US6043393A
  申请人：——

  公开号：US6043393A

  公开（公告）日：2000-03-28
• [DE] VERFAHREN ZUR HERSTELLUNG VON CYCLOPROPYLAMINEN<br/>[EN] METHOD FOR PREPARING CYCLOPROPYLAMINES<br/>[FR] PROCEDE DE PREPARATION DE CYCLOPROPYLAMINES
  申请人：——

  公开号：WO1998022425A1

  公开（公告）日：1998-05-28

  [EN] Method for producing cyclopropylamines by making a carbonic acid amide react with an olefin under the influence of alkylmagnesium halogenides or zinc alkyl compounds and orthometallates.
  [FR] L'invention concerne un procédé de préparation de cyclopropylamines par réaction d'un amide d'acide carboxylique avec une oléfine, sous l'effet d'halogénure de magnésium d'alkyle ou de composés d'alkyle de zinc et d'orthométallates.
  [DE] Verfahren zur Herstellung von Cyclopropylaminen durch Umsetzung eines Carbonsäureamids mit einem Olefin unter der Einwirkung von Alkylmagnesiumhalogeniden oder Zinkalkylverbindungen und von Orthometallaten.
• The Kulinkovich Reaction in the Synthesis of Constrained <i>N,N</i>-Dialkyl Neurotransmitter Analogues
  作者：Catherine A. Faler、Madeleine M. Joullié

  DOI：10.1021/ol0705907

  日期：2007.5.1

  An intermolecular Ti(IV)-mediated cyclopropanation reaction has been used to synthesize substituted 2-phenylcyclopropylamines and constrained analogues of the neurotransmitters histamine and tryptamine. Many hydroxy- and methoxy-substituted phenylcyclopropylamines are known to inhibit monoamine oxidase and have been shown to mimic hallucinogens. These compounds were made in 1 to 5 steps from readily available starting materials.