5-chloro-2-(hex-1-yn-1-yl)aniline

• 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: 5-chloro-2-(hex-1-yn-1-yl)aniline
• 英文别名: 5-Chloro-2-hex-1-ynylaniline
• 化学式: C₁₂H₁₄ClN
• 分子量: 207.703
• InChiKey: BECAOKKRBHRMRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(hex-1-yn-1-yl)aniline 在 盐酸 、 水 、 sodium nitrite 作用下， 反应 0.17h， 以86%的产率得到3-n-butyl-7-chloro-1H-cinnolin-4-one
  参考文献：
  名称：

  A convenient and efficient protocol for the synthesis of 4(1H)-cinnolones, 1,4-dihydrocinnolines, and cinnolines in aqueous medium: application for detection of nitrite ions

  摘要：

  3-Aryl/alkyl-4(1H)-cinnolones are obtained in one step from 2-aryl/alkylethynyl aniline by reaction with sodium nitrite and dilute hydrochloric acid via Richter cyclization. The alkyl cinnolones on reduction with Sn/HCl furnish 1,4-dihydro-3-alkylcinnolines, which are converted to 3-alkylcinnolines by treatment with NaNO2/HCl/KI. The whole process is carried out in aqueous medium at ambient temperature within a short reaction period. The reaction of 2-phenylethynyl aniline exhibits yellow color with UV absorbance at 391 nm and has been successfully tested for the detection of nitrite ions in water at parts per million concentration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.016
• 作为产物：
  描述：

  5-氯-2-碘苯胺 、 1-己炔 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II) dichloride 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-chloro-2-(hex-1-yn-1-yl)aniline
  参考文献：
  名称：

  Simple Indole Synthesis by One-Pot Sonogashira Coupling-NaOH-Mediated Cyclization

  摘要：

  在标准Sonogashira条件下，将o-碘苯胺与末端炔烃偶联，并在常规加热或微波辐照下进一步处理NaOH，通常可以获得高产率的2-取代吲哚。在反应条件下，卤素、硝基和氰基等功能团均可耐受。

  DOI：

  10.1055/s-0028-1083624

文献信息

• Simple Indole Synthesis by One-Pot Sonogashira Coupling-NaOH-Mediated Cyclization
  作者：Roberto Sanz、Verónica Guilarte、M. Castroviejo

  DOI：10.1055/s-0028-1083624

  日期：2008.12

  Coupling of o-iodoanilines with terminal alkynes under standard Sonogashira conditions, and further treatment with NaOH under conventional heating or microwave irradiation, afford 2-substituted indoles in usually high yields. Functionalities such as halides, nitro, and cyano groups are tolerated under the reaction conditions.

  在标准Sonogashira条件下，将o-碘苯胺与末端炔烃偶联，并在常规加热或微波辐照下进一步处理NaOH，通常可以获得高产率的2-取代吲哚。在反应条件下，卤素、硝基和氰基等功能团均可耐受。
• Crossover-Annulation/Oxygenation Approach to Functionalized Phenanthridines by Palladium–Copper Relay Catalysis
  作者：Xiang Liu、Renjie Mao、Cheng Ma

  DOI：10.1021/acs.orglett.7b03427

  日期：2017.12.15

  A tandem crossover-annulation and oxygenation process of conjugated enediyne-acids and ortho-alkynylanilines was achieved by palladium-copper relay catalysis under an oxygen atmosphere, giving access to the three-component assembly of 9-acylphenanthridine compounds.
• A Robust, Well-Defined Homogeneous Silver(I) Catalyst for Mild Intramolecular Hydroamination of 2-Ethynylanilines Leading to Indoles
  作者：James McNulty、Kunal Keskar

  DOI：10.1002/ejoc.201301368

  日期：2014.3

  A highly efficient, chemically stable and well-defined homogeneous silver(I) catalyst is reported for the room temperature, intramolecular hydroamination of 2-alkynylanilines leading to indole derivatives.

  据报道，一种高效、化学稳定且定义明确的均相银 (I) 催化剂可用于室温下 2-炔基苯胺的分子内加氢胺化，从而生成吲哚衍生物。
• A convenient and efficient protocol for the synthesis of 4(1H)-cinnolones, 1,4-dihydrocinnolines, and cinnolines in aqueous medium: application for detection of nitrite ions
  作者：Raju Dey、Brindaban C. Ranu

  DOI：10.1016/j.tet.2011.09.016

  日期：2011.11

  3-Aryl/alkyl-4(1H)-cinnolones are obtained in one step from 2-aryl/alkylethynyl aniline by reaction with sodium nitrite and dilute hydrochloric acid via Richter cyclization. The alkyl cinnolones on reduction with Sn/HCl furnish 1,4-dihydro-3-alkylcinnolines, which are converted to 3-alkylcinnolines by treatment with NaNO2/HCl/KI. The whole process is carried out in aqueous medium at ambient temperature within a short reaction period. The reaction of 2-phenylethynyl aniline exhibits yellow color with UV absorbance at 391 nm and has been successfully tested for the detection of nitrite ions in water at parts per million concentration. (C) 2011 Elsevier Ltd. All rights reserved.