N-(pent-3-yn-1-yl)aniline | 196085-16-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(pent-3-yn-1-yl)aniline
• 英文别名: N-3-Pentyn-1-ylbenzenamine；N-pent-3-ynylaniline
• CAS: 196085-16-2
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: NUJXMPBAXYYZOK-UHFFFAOYSA-N

物化性质

• 沸点：
  289.1±23.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(pent-3-yn-1-yl)aniline 在 正丁基锂 、 zirconocene methyl chloride 、 氘代硫酸 作用下， 生成 (1S,4S)-2,5-bis[(E)-1-deuterioethylidene]-N,N'-diphenyl-1,4-cyclohexanediamine
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling Reactions of Unsaturated Anilines. Diastereoselective Synthesis of Azetidines

  摘要：

  Imine complexes of zirconocene, generated by a beta-hydrogen abstraction process, which possess a carbon-carbon multiple bond, undergo inter-or intramolecular carbometalation to afford 1,4-cyclohexanediamine or cycloalkylaniline derivatives depending on the relative position of the unsaturated moiety with respect to the imine complex. A new diastereoselective synthesis of azetidines has been developed by treatment of azazirconacyclopentanes with iodine.

  DOI：

  10.1021/jo9705780
• 作为产物：
  描述：

  3-戊炔-1-醇 在 氢氧化钾 作用下， 以 乙醚 、 水 为溶剂， 生成 N-(pent-3-yn-1-yl)aniline
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling Reactions of Unsaturated Anilines. Diastereoselective Synthesis of Azetidines

  摘要：

  Imine complexes of zirconocene, generated by a beta-hydrogen abstraction process, which possess a carbon-carbon multiple bond, undergo inter-or intramolecular carbometalation to afford 1,4-cyclohexanediamine or cycloalkylaniline derivatives depending on the relative position of the unsaturated moiety with respect to the imine complex. A new diastereoselective synthesis of azetidines has been developed by treatment of azazirconacyclopentanes with iodine.

  DOI：

  10.1021/jo9705780

文献信息

• 一种铜催化的四氢吡咯并喹啉衍生物的制备 方法及应用
  申请人：杭州市第一人民医院

  公开号：CN106565709B

  公开（公告）日：2018-06-08

  本发明公开了一种四氢吡咯并喹啉衍生物的制备方法，包括如下步骤：将氯化亚铜与氨基炔、炔烃加入反应瓶中，向其中加入溶剂DMF，微波照射下，150℃反应30分钟得目标产物。该方法收率高，时间快，成本低，所用底物不局限于末端炔烃，对末端炔和非末端炔均具有良好的适用性，解决了金催化该反应的缺陷，该方法制备的部分化合物经细胞活性测试，具有肿瘤细胞增殖抑制活性，表明该方法在抗肿瘤药物发现中具有潜在的应用价值。
• Trapping rhodium carbenoids with aminoalkynes for the synthesis of diverse N-heterocycles
  作者：Arianne C. Hunter、Bilal Almutwalli、Anae I. Bain、Indrajeet Sharma

  DOI：10.1016/j.tet.2018.06.042

  日期：2018.9

  A convergent approach for the synthesis of diverse N-heterocycles is described. The reaction involves trapping of diazo-derived rhodium carbenoids with gold activated aminoalkynes, and accommodates both the donor/acceptor (D/A) as well as acceptor/acceptor (A/A) diazo carbonyls. Mechanistic investigations indicate that the Rh(II)/Au(I) catalyzed reaction of aminoalkynes with D/A diazos is concerted

  描述了一种用于合成各种N-杂环的收敛方法。该反应涉及用金活化的氨基炔捕获重氮衍生的铑类胡萝卜素，并容纳供体/受体（D / A）以及受体/受体（A / A）重氮羰基。机理研究表明，Rh（II）/ Au（I）催化氨基炔与D / A重氮的反应是协调的，而与A / A重氮的反应是逐步进行的，并进行卡宾N–H插入和随后的Conia-ene环化。
• A convenient titanium-mediated intermolecular alkyne–carbonate coupling reaction
  作者：Andrzej Wolan、Frédéric Cadoret、Yvan Six

  DOI：10.1016/j.tet.2009.07.015

  日期：2009.9

  A direct diastereoselective titanium-mediated intermolecular coupling of internal alkynes with dialkyl carbonates under Kulinkovich-type reaction conditions is presented. The influence of the structures of the coupling partners on the yields and regioselectivities of this transformation is described. (C) 2009 Elsevier Ltd. All rights reserved.
• Structure and Dynamic Behavior of Phosphine Gold(I)-Coordinated Enamines: Characterization of α-Metalated Iminium Ions
  作者：Madhavi Sriram、Yuyang Zhu、Andrew M. Camp、Cynthia S. Day、Amanda C. Jones

  DOI：10.1021/om500670z

  日期：2014.8.25
• Zirconium-Mediated Intramolecular Coupling Reactions of Unsaturated Anilines. Diastereoselective Synthesis of Azetidines
  作者：José Barluenga、Roberto Sanz、Francisco J. Fañanás

  DOI：10.1021/jo9705780

  日期：1997.8.1

  Imine complexes of zirconocene, generated by a beta-hydrogen abstraction process, which possess a carbon-carbon multiple bond, undergo inter-or intramolecular carbometalation to afford 1,4-cyclohexanediamine or cycloalkylaniline derivatives depending on the relative position of the unsaturated moiety with respect to the imine complex. A new diastereoselective synthesis of azetidines has been developed by treatment of azazirconacyclopentanes with iodine.