N-(3-butynyl)-N-methylaniline | 137273-33-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-butynyl)-N-methylaniline
• 英文别名: N-(but-3-ynyl)-N-methylaniline；but-3-ynyl-methyl-phenyl-amine；Benzenamine, N-3-butynyl-N-methyl-；N-but-3-ynyl-N-methylaniline
• CAS: 137273-33-7
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: YVSNCSAARRCSPB-UHFFFAOYSA-N

物化性质

• 沸点：
  245.3±23.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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-(3-butynyl)-N-methylaniline 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Gold or No Gold: One-Pot Synthesis of Tetrahydrobenz[b]azepin-4-ones from Tertiary N-(But-3-ynyl)anilines

  摘要：

  Depending on the tertiary aniline substrates, an efficient, one-pot synthesis of tetrahydrobenz[b]azepin-4-ones needs either gold catalysts or no catalyst at all. In the reaction, the aniline nitrogen plays a unique role in relaying "O" from m-CPBA to a tethered C-C triple bond, which is inert to the oxidant under the mild reaction conditions.

  DOI：

  10.1021/ol900027h
• 作为产物：
  描述：

  N-甲基苯胺 在 bismuth(III) chloride 、 氢化铝 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N-(3-butynyl)-N-methylaniline
  参考文献：
  名称：

  Water-tolerant unstabilized carbanion equivalents: Bismuth(III) chloride-aluminum promoted alkylations of immonium cations to amines in aqueous Media

  摘要：

  In the presence of bismuth(III) chloride-metallic aluminum, alkyl as well as allyl halides react with N-(alkylamino)benzotriazoles at 20-degrees-C in THF-water to give the corresponding homoalkylated amines in high yields.

  DOI：

  10.1016/s0040-4039(00)92139-7

文献信息

• Gold(<scp>i</scp>)-catalyzed formation of dihydroquinolines and indoles from N-aminophenyl propargyl malonates
  作者：Colombe Gronnier、Yann Odabachian、Fabien Gagosz

  DOI：10.1039/c0cc00033g

  日期：——

  The use of [XPhosAu(NCMe)]SbF(6) in nitromethane at 100 degrees C allows the rapid and efficient formation of variously substituted dihydroquinolines, which can be subsequently converted into indoles by a rare photochemical rearrangement.

  在100℃的硝基甲烷中使用[XPhosAu（NCMe）] SbF（6）可以快速有效地形成各种取代的二氢喹啉，随后可通过罕见的光化学重排将其转化为吲哚。
• Gold(I)-Catalyzed Oxidative Amination of β-Amino-ynones to Quaternary Ammonium-olate Salts: The Benefit of a P,N-Bidentate Ligand
  作者：Jing Guo、Zi-Sheng Chen、Wen-Shuai Chen、Xin Zhao、Kegong Ji

  DOI：10.1021/acs.orglett.1c03382

  日期：2021.11.19

  A novel P,N-bidentate ligand-assisted gold-catalyzed oxidative amination of β-amino-ynones has been developed, allowing the simple and efficient construction of various quaternary ammonium-olate salts in good to excellent yields. These unprecedented quaternary ammonium-olate salts can be isolated and purified via simple suction filtration. The broad substrate scope, easy purification, easy further

  已经开发了一种新型的 P,N-二齿配体辅助金催化的 β-氨基炔酮氧化胺化，可以简单有效地构建各种季铵盐，收率良好。这些前所未有的季铵盐可以通过简单的抽滤分离和纯化。广泛的底物范围、易于纯化、易于进一步转化和温和的条件使其成为合成各种季铵盐的可行替代品。
• Silver‐Catalyzed Tandem Cyclization for Syntheses of Azaoxa‐ and Diazaspirocycles**
  作者：Momoka Shimaoka、Masahiro Sai

  DOI：10.1002/ejoc.202201404

  日期：2023.3

  Therefore, researchers have tried to develop efficient catalytic systems to access this scaffold. This work reports the synthesis of various azaoxa- and diazaspirocycles from alkynes bearing two pendant nitrogen- and oxygen-based nucleophiles under silver catalysis.

  1-Azaspirocycles 代表在许多批准的药物和天然产品中发现的重要结构基序。因此，研究人员试图开发有效的催化系统来访问该支架。这项工作报道了在银催化下，从带有两个悬垂的氮基和氧基亲核试剂的炔烃中合成各种氮杂氧杂环和二氮杂螺环。
• Gallium Mediated Allylation and Propargylation of 1-(α-Aminoalkyl)benzotriazole: An Alternative Route to Homoallylic and Homopropargyl Amines
  作者：Weiliang Bao、Yongmin Zhang

  DOI：10.1080/00397919708003333

  日期：1997.2

  Mediated by gallium metal 1-(alpha-aminoalkyl)benzotriazole reacted with allylic and propargyl bromide to give homoallylic and homopropargyl amines in moderate to good yields.
• Gold or No Gold: One-Pot Synthesis of Tetrahydrobenz[<i>b</i>]azepin-4-ones from Tertiary <i>N</i>-(But-3-ynyl)anilines
  作者：Li Cui、Guozhu Zhang、Yu Peng、Liming Zhang

  DOI：10.1021/ol900027h

  日期：2009.3.19

  Depending on the tertiary aniline substrates, an efficient, one-pot synthesis of tetrahydrobenz[b]azepin-4-ones needs either gold catalysts or no catalyst at all. In the reaction, the aniline nitrogen plays a unique role in relaying "O" from m-CPBA to a tethered C-C triple bond, which is inert to the oxidant under the mild reaction conditions.