2-methyl-N-(3-phenylprop-2-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: 2-methyl-N-(3-phenylprop-2-yn-1-yl)aniline
• 英文别名: 2-methyl-N-(3-phenylprop-2-ynyl)aniline
• 化学式: C₁₆H₁₅N
• mdl: MFCD17057068
• 分子量: 221.302
• InChiKey: GDINGGFNHYPIFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 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：

  2-methyl-N-(3-phenylprop-2-yn-1-yl)aniline 在 silver(I) nitrite 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到3-phenyl-1-(o-tolyl)-1H-pyrazole 2-oxide
  参考文献：
  名称：

  AgNO₂ as the NO Source for the Synthesis of Substituted Pyrazole N-Oxides from N-Propargylamines

  摘要：

  A straightforward method for synthesizing the pyrazole N-oxides from N-propargylamines and AgNO2, through oxidation/cyclization reaction had been developed. AgNO2, was used as the NO source for the first time to synthesize pyrazole N-oxides. Various substituted groups on N-propargylamines proceeded smoothly, and the desired products were obtained in good yields.

  DOI：

  10.1021/acs.orglett.6b03021
• 作为产物：
  描述：

  邻甲苯胺 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， 反应 12.08h， 生成 2-methyl-N-(3-phenylprop-2-yn-1-yl)aniline
  参考文献：
  名称：

  AgNO₂ as the NO Source for the Synthesis of Substituted Pyrazole N-Oxides from N-Propargylamines

  摘要：

  A straightforward method for synthesizing the pyrazole N-oxides from N-propargylamines and AgNO2, through oxidation/cyclization reaction had been developed. AgNO2, was used as the NO source for the first time to synthesize pyrazole N-oxides. Various substituted groups on N-propargylamines proceeded smoothly, and the desired products were obtained in good yields.

  DOI：

  10.1021/acs.orglett.6b03021

文献信息

• 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。
• Ag-Catalyzed or Ag/PPh₃-Catalyzed Chemoselective Switchable Cascade Reactions of <i>N</i>-Propargyl Thiocarbamoyl Fluorides and Malonate Esters
  作者：Zhongliang Cai、Junyi Zhou、Miao Yu、Liqin Jiang

  DOI：10.1021/acs.orglett.1c03950

  日期：2022.1.14

  The divergent chemoselective synthesis of 2-methylene-2,3-dihydrothiazoles and 4-benzylidene pyrrolidine-2-thiones (most with E stereoselectivity) from N-propargyl thiocarbamoyl fluorides and malonate esters in moderate to excellent yields with a broad substrate scope and functional group tolerance has been accomplished. AgNTf2 catalyst at 60 °C in dichloroethane provided 4-benzylidene pyrrolidine-2-thiones

  从N-炔丙基硫代氨基甲酰氟和丙二酸酯以中等至优异的产率，具有广泛的底物范围和功能性，不同的化学选择性合成 2-亚甲基-2,3-二氢噻唑和 4-亚苄基吡咯烷-2-硫酮（大多数具有 E 立体选择性）群体容忍度已经完成。AgNTf 2催化剂在 60 °C 下在二氯乙烷中提供 4-亚苄基吡咯烷-2-硫酮。AgOTf 催化剂和 PPh 3配体在回流乙腈中导致形成的 α,α-二酯硫代酰胺中间体的反应性发生完全转换，随后异构化得到 2-亚甲基-2,3-二氢噻唑。