N-[1-(benzotriazol-1-yl)butyl]-N-methylaniline | 132553-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-[1-(benzotriazol-1-yl)butyl]-N-methylaniline
• CAS: 132553-21-0
• 化学式: C₁₇H₂₀N₄
• 分子量: 280.373
• InChiKey: NDNOLSCDORFCSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[1-(benzotriazol-1-yl)butyl]-N-methylaniline 、 3-戊酮 在 samarium diiodide 、 2-<α-(phenylmethylamino)butyl>benzotriazole 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 4.0h， 以25%的产率得到N-甲基苯胺
  参考文献：
  名称：

  N-(α-Aminoalkyl)benzotriazoles:  Novel “Nonstabilized” α-Aminocarbanion Synthons

  摘要：

  C-Benzotriazole bonds were selectively transformed to give the corresponding alpha-aminocarbanions when N-(alpha-aminoalkyl)benzotriazoles were reacted with either Li/LiBr or SmI2 in the presence of representative electrophiles. The ranges of applicability of the two reagents complement each other, and together the two protocols provide a general route from readily available crystalline starting materials to a variety of ''nonstabilized'' alpha-aminocarbanions that can be trapped in moderate to good yields.

  DOI：

  10.1021/jo962247d
• 作为产物：
  描述：

  T406石油添加剂 、 正丁醛 、 N-甲基苯胺 以 乙醚 为溶剂， 生成 2-<α-(phenylmethylamino)butyl>benzotriazole 、 N-[1-(benzotriazol-1-yl)butyl]-N-methylaniline
  参考文献：
  名称：

  苯并三唑辅助合成烯胺

  摘要：

  分两步完成新的简便的烯胺制备：（i）由等摩尔量的苯并三唑，醛和仲胺容易地形成N-（α-氨基烷基）苯并三唑衍生物（ii）在四氢呋喃（THF）中用氢化钠消除衍生物中的苯并三唑。该方法基于所用胺的量提供了良好的总收率的烯胺。

  DOI：

  10.1016/s0040-4020(01)81471-x

文献信息

• Lewis acid assisted reactions of<i>N</i>-(α- aminoalkyl)benzotriazoles and unactivated alkenes for the facile synthesis of 4-, 2,4-, and 3,4-substituted 1,2,3,4-tetrahydroquinolines
  作者：Alan R. Katritzky、Daniel A. Nichols、Ming Qi、Baozhen Yang

  DOI：10.1002/jhet.5570340428

  日期：1997.7

  A range of substituted tetrahydroquinolines have been synthesized from benzotriazole derivatives and unactivated alkenes in the presence of a Lewis acid. These reactions utilize readily available starting materials and mild reaction conditions, and give high yields. The reaction mechanisms are discussed.

  在路易斯酸的存在下，由苯并三唑衍生物和未活化的烯烃合成了一系列取代的四氢喹啉。这些反应利用容易获得的原料和温和的反应条件，并获得高收率。讨论了反应机理。
• Benzotriazole-assisted synthesis of enamines
  作者：Alan R. Katritzky、Qiu-He Long、Ping Lue、Andrzej Jozwiak

  DOI：10.1016/s0040-4020(01)81471-x

  日期：——

  A new, facile preparation of enamines was achieved via a two-step sequence: (i) the ready formation of an N-(α-aminoalkyl)benzotriazole derivative from equimolar amounts of benzotriazole, an aldehyde, and a secondary amine, (ii) the elimination of benzotriazole from the derivative by sodium hydride in tetrahydrofuran (THF). The method provides enamines in good overall yields based on the quantity of

  分两步完成新的简便的烯胺制备：（i）由等摩尔量的苯并三唑，醛和仲胺容易地形成N-（α-氨基烷基）苯并三唑衍生物（ii）在四氢呋喃（THF）中用氢化钠消除衍生物中的苯并三唑。该方法基于所用胺的量提供了良好的总收率的烯胺。
• <i>N</i>-(α-Aminoalkyl)benzotriazoles:  Novel “Nonstabilized” α-Aminocarbanion Synthons
  作者：Alan R. Katritzky、Ming Qi、Daming Feng、Daniel A. Nichols

  DOI：10.1021/jo962247d

  日期：1997.6.13

  C-Benzotriazole bonds were selectively transformed to give the corresponding alpha-aminocarbanions when N-(alpha-aminoalkyl)benzotriazoles were reacted with either Li/LiBr or SmI2 in the presence of representative electrophiles. The ranges of applicability of the two reagents complement each other, and together the two protocols provide a general route from readily available crystalline starting materials to a variety of ''nonstabilized'' alpha-aminocarbanions that can be trapped in moderate to good yields.