4-methoxy-N-(3-phenylprop-2-yn-1-yl)aniline | 1217436-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxy-N-(3-phenylprop-2-yn-1-yl)aniline
• 英文别名: 4-methoxy-N-(3-phenylprop-2-ynyl)aniline
• CAS: 1217436-55-9
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: SYGAVEXEEBIXAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(3-phenylprop-2-yn-1-yl)aniline 在 碘 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Heterocyclic Iodoniums for the Assembly of Oxygen-Bridged Polycyclic Heteroarenes with Water as the Oxygen Source

  摘要：

  A diverse set of novel heterocyclic iodoniums was synthesized for the first time. The reactions of these unique iodoniums with environmentally benign water as the oxygen source provided structurally complex oxygen-incorporated heteropolycycles that are essential motifs in natural products and biologically active compounds. The transformation only required low-cost copper acetate. Further derivatization of the obtained polycycles expanded the structural diversity, which is important in the building of chemical libraries for drug discovery.

  DOI：

  10.1021/acs.orglett.8b01969
• 作为产物：
  描述：

  甲氧苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-methoxy-N-(3-phenylprop-2-yn-1-yl)aniline
  参考文献：
  名称：

  Heterocyclic Iodoniums for the Assembly of Oxygen-Bridged Polycyclic Heteroarenes with Water as the Oxygen Source

  摘要：

  A diverse set of novel heterocyclic iodoniums was synthesized for the first time. The reactions of these unique iodoniums with environmentally benign water as the oxygen source provided structurally complex oxygen-incorporated heteropolycycles that are essential motifs in natural products and biologically active compounds. The transformation only required low-cost copper acetate. Further derivatization of the obtained polycycles expanded the structural diversity, which is important in the building of chemical libraries for drug discovery.

  DOI：

  10.1021/acs.orglett.8b01969

文献信息

• Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines
  作者：Xiaoxia Zhang、Tuanli Yao、Marino A. Campo、Richard C. Larock

  DOI：10.1016/j.tet.2009.12.012

  日期：2010.2

  A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr, and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the

  通过 ICl、I 2、Br 2、PhSeBr 和p -O 2 NC 6 H对N -(2-炔基)苯胺进行6-内位亲电环化，可以在温和的反应条件下轻松合成各种取代的喹啉。4 SCl。该反应在各种官能团存在下以中等至良好的产率提供含3-卤素、硒和硫的喹啉。通过Hg(OTf) 2催化这些相同的炔基苯胺的闭环，已经合成了在3-位带有氢的类似喹啉。
• Synthesis of 3-sulfonylquinolines by visible-light promoted metal-free cascade cycloaddition involving <i>N</i>-propargylanilines and sodium sulfinates
  作者：Jing-Mei Yuan、Jinnan Li、Heyang Zhou、Jiali Xu、Fengting Zhu、Qiuli Liang、Zhiping Liu、Guobao Huang、Jun Huang

  DOI：10.1039/c9nj05248h

  日期：——

  A visible-light promoted radical cascade reaction of N-propargylanilines with sodium sulfinates as sulfonyl radical precursors was developed under metal-free conditions.

  开发了一种在无金属条件下，可见光促进的以亚砜基自由基前体为硫醇基自由基前体的N-丙炔基苯胺的自由基级联反应。
• Visible-light-induced multicomponent cascade cycloaddition involving <i>N</i>-propargyl aromatic amines, diaryliodonium salts and sulfur dioxide: rapid access to 3-arylsulfonylquinolines
  作者：Deli Sun、Kun Yin、Ronghua Zhang

  DOI：10.1039/c7cc09410h

  日期：——

  A visible-light-induced, Eosin Y catalyzed three-component synthesis of 3-arylsulfonylquinoline derivatives through N-propargyl aromatic amines, diaryliodonium salts and sulfur dioxide has been discovered. This transformation represents an efficient and attractive method for the straightforward synthesis of 3-arylsulfonylquinoline derivatives via the formation of C–S bonds and quinolines in one step

  已经发现了可见光诱导的曙红Y通过N-炔丙基芳族胺，二芳基碘鎓盐和二氧化硫催化的3-芳基磺酰基喹啉衍生物的三组分合成。这种转变代表了通过一步形成C–S键和喹啉直接合成3-芳基磺酰基喹啉衍生物的一种有效且有吸引力的方法。另外，它表现出良好的底物范围和官能团耐受性。易处理的二芳基碘鎓盐，二氧化硫源和廉价的光催化剂曙红Y的使用以及在室温下的简便操作，使该方案非常实用。
• Electrooxidative tandem cyclization of <i>N</i>-propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives
  作者：Jie Liu、Min Wang、Laiqiang Li、Lei Wang

  DOI：10.1039/d1gc00171j

  日期：——

  A series of N-propargylanilines (0.2 mmol) and sulfinic acids (0.5 mmol) afforded 3-arylsulfonylquinoline derivatives in high yields (70–93%) and low current efficiencies upon electrooxidation. Electrolyses were carried out in a one-compartment cell, under constant current and ambient conditions, in methanol-nBu4NBF4 containing pyridine (0.4 mmol), without any added chemical oxidant. A scale-up electrolysis

  一系列N-炔丙基苯胺（0.2 mmol）和亚磺酸（0.5 mmol）以高收率（70-93％）和低电氧化效率提供了3-芳基磺酰基喹啉衍生物。在恒定电流和环境条件下，在单隔室的电解池中，在不添加任何化学氧化剂的，含有吡啶（0.4 mmol）的甲醇-n Bu 4 NBF 4中进行电解。在5mmol的N-炔丙基苯胺1a上进行放大电解，得到3-芳基磺酰基喹啉3aa，产率为65％，电流效率为56％。提出了机械学假说。
• A visible-light-induced oxidative cyclization of <i>N</i>-propargylanilines with sulfinic acids to 3-sulfonated quinoline derivatives without external photocatalysts
  作者：Yicheng Zhang、Wei Chen、Xueshun Jia、Lei Wang、Pinhua Li

  DOI：10.1039/c8cc10235j

  日期：——

  A visible-light-induced oxidative cyclization of N-propargyl anilines with sulfinic acids was developed under external photocatalyst-free conditions. The reaction provides a straightforward route to 3-sulfonated quinoline derivatives with good functional group tolerance, excellent yields and high regio-selectivity.

  在无外部光催化剂的条件下，可见光诱导了亚磺酸与N-炔丙基苯胺的氧化环化反应。该反应提供了具有良好的官能团耐受性，优异的产率和高的区域选择性的3-磺化喹啉衍生物的直接途径。