3-methyl-N-(3-phenylprop-2-yn-1-yl)aniline | 121194-52-3

• 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: 3-methyl-N-(3-phenylprop-2-yn-1-yl)aniline
• 英文别名: 3-methyl-N-(3-phenylprop-2-ynyl)aniline
• CAS: 121194-52-3
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: SDKPIMNCSQEEIM-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：
  0.12
• 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：

  3-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77%的产率得到3-phenyl-1-(m-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：

  3-甲基苯胺 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 3-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

• 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。
• Visible-Light-Induced Multicomponent Cascade Cycloaddition of <i>N</i>-Propargyl Aromatic Amines, Cyclobutanone Oxime Esters, and K₂S₂O₅: Access to Cyanoalkylsulfonylated Quinolines
  作者：Nengneng Zhou、Ziqin Xia、Sixin Wu、Kaimo Kuang、Qiankun Xu、Man Zhang

  DOI：10.1021/acs.joc.1c01866

  日期：2021.11.5

  A visible-light-induced cascade cyanoalkylsulfonylation/cyclization/aromatization of N-propargyl aromatic amines with K2S2O5 and cyclobutanone oxime esters for the construction of cyanoalkylsulfonylated quinolines is developed. This cascade transformation features mild reaction conditions, a broad substrate scope, and excellent functional group compatibility, providing a convenient route toward cy

  开发了N-炔丙基芳香胺与 K 2 S 2 O 5和环丁酮肟酯的可见光诱导级联氰烷基磺酰化/环化/芳构化，用于构建氰烷基磺酰化喹啉。这种级联转化具有反应条件温和、底物范围广、官能团兼容性好等特点，通过一步形成一个 C-C 键和两个 C-S 键，提供了一条通往氰基烷基磺酰化喹啉的便捷途径。
• Copper‐Catalyzed Electrophilic Cyclization of <i>N</i> ‐Propargylamines with Sodium Sulfinate for the Synthesis of 3‐Sulfonated Quinolines
  作者：Ling Li、Xing‐Guo Zhang、Bo‐Lun Hu、Xiao‐Hong Zhang

  DOI：10.1002/asia.201901298

  日期：2019.12.2

  A convenient and effective protocol for the synthesis of 3-sulfonated quinolines via copper-catalyzed electrophilic cyclization of N-propargylamines has been developed, in which cheap and stable sodium sulfinates were utilized as green sulfonylation reagents. This cascade transformation involves radical addition, cyclization and dehydrogenative aromatization processes in a one-pot reaction under mild

  通过铜催化的N-炔丙基胺的亲电子环化反应，合成了一种方便，有效的3-磺化喹啉的方法，其中廉价，稳定的亚磺酸钠被用作绿色磺酰化试剂。这种级联转化包括在温和条件下的一锅反应中的自由基加成，环化和脱氢芳构化过程。
• 3-磺酰喹啉衍生物的合成方法
  申请人：温州大学

  公开号：CN110467572B

  公开（公告）日：2022-07-08

  本发明涉及一种3‑磺酰喹啉衍生物的合成方法，包括以下步骤：以N‑芳丙炔芳胺和芳基(烷基)亚磺酸钠为底物，叔丁基过氧化氢作氧化剂，CuI为催化剂，四丁基硫酸氢铵和冰乙酸作添加剂，1,2‑二氯乙烷作溶剂，于70℃～90℃搅拌反应10～12小时。反应结束后，过滤反应液，并将滤液用旋转蒸发仪除去溶剂获得剩余物，通过硅胶柱对剩余物进行柱层分离，并经洗脱液进行淋洗，收集含有目标产物的流出液，合并流出液并经过真空浓缩除去溶剂获得目标产物。本发明具有原料简单易得，制备工艺新颖、简单、污染少、耗能低、产率高、反应时间短的优点。