o-(N-methylamino)-N'-prop-2-inylbenzamide | 35727-71-0

• 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: o-(N-methylamino)-N'-prop-2-inylbenzamide
• 英文别名: propargyl N-methyl anthranilamide；PMA；2-Methylamino-benzoesaeure-；2-(Methylamino)-N-(prop-2-yn-1-yl)benzamide；2-(methylamino)-N-prop-2-ynylbenzamide
• CAS: 35727-71-0
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: INICZKWGLIMWFW-UHFFFAOYSA-N

物化性质

• 沸点：
  374.4±27.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  o-(N-methylamino)-N'-prop-2-inylbenzamide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以65%的产率得到2-(2'-N-methylaminophenyl)-5-methyloxazole
  参考文献：
  名称：

  Reisch; Usifoh; Okoh, Pharmazie, 1992, vol. 47, # 1, p. 18 - 20

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基苯唑 、 炔丙胺 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到o-(N-methylamino)-N'-prop-2-inylbenzamide
  参考文献：
  名称：

  Reisch; Usifoh; Okoh, Pharmazie, 1992, vol. 47, # 1, p. 18 - 20

  摘要：

  DOI：

文献信息

• Copper-catalyzed one-pot process to construct triazole-linked urea derivatives
  作者：Kung-Kai Kuo、Siva Senthil Kumar Boominathan、Jaya Kishore Vandavasi、Jia-Shing Hsiao、Jeh-Jeng Wang、Wan-Ping Hu

  DOI：10.1080/00397911.2016.1218896

  日期：2016.10.1

  ABSTRACT A new one-pot synthetic methodology has been developed to construct the triazole-linked urea derivatives. In the same step, triazole forms from azide and alkyne via click reaction and urea forms from addition reaction of amines and isocyanates. The notable features of this work include wide substrate scope, atom economy, environmental friendliness, and easily accessible starting materials

  摘要开发了一种新的一锅合成方法来构建三唑连接的尿素衍生物。在同一步骤中，叠氮化物和炔烃通过点击反应形成三唑，胺和异氰酸酯的加成反应形成尿素。这项工作的显着特点包括广泛的底物范围、原子经济性、环境友好性和易于获取的起始材料。合成化合物的初步生物筛选在基底细胞癌 (BCC) 细胞系中显示出有希望的细胞毒活性。图形概要
• Mantyl tagged oligo α (1 → 2) mannosides as Candida albicans β-mannosyl transferases substrates: a comparison between synthetic strategies
  作者：Marilyne Pourcelot、Laurent Cattiaux、Ghenima Sfihi-Loualia、Emeline Fabre、Frédéric Krzewinski、Chantal Fradin、Daniel Poulain、Florence Delplace、Yann Guérardel、Jean-Maurice Mallet

  DOI：10.1039/c3ra43340d

  日期：——

  Fluorescent oligomannosides are important tools for the evaluation of mannosyl transferase activities and selectivities. In a project dealing with Candida albicans β-mannosyl transferases, three mantyl tagged α (1 → 2) oligomannosides were prepared by different ways: using all ester strategy compatible with the presence of an azido group suitable for direct click chemistry; and alternatively using the more classic benzyl protecting groups. Although more elegant, the all ester strategy has shown important limitations: reduced reactivity of mannosyl donors, and 3 → 2 ester migration. Preliminary enzymatic studies have shown that the synthetic oligomannosides are efficient substrate of β-mannosyl transferases.

  荧光寡甘露糖苷是评估甘露基转移酶活性和选择性的重要工具。在一个研究白色念珠菌δ-甘露糖基转移酶的项目中，通过不同的方法制备了三种曼特基标记的δ（1â2）低聚甘露糖苷：使用与叠氮基团兼容的全酯策略，适合直接点击化学；或者使用更经典的苄基保护基团。尽管全酯策略更为优雅，但也显示出重要的局限性：甘露糖苷供体的反应性降低，以及 3 - 2 酯迁移。初步的酶学研究表明，合成的低聚甘露糖苷是δ-甘露糖苷转移酶的有效底物。
• Facile, Selective, and Regiocontrolled Synthesis of Oxazolines and Oxazoles Mediated by ZnI₂ and FeCl₃
  作者：Gopal Chandru Senadi、Wan-Ping Hu、Jia-Shing Hsiao、Jaya Kishore Vandavasi、Chung-Yu Chen、Jeh-Jeng Wang

  DOI：10.1021/ol301980g

  日期：2012.9.7

  An expedient method for a direct approach to the selective and regiocontrolled synthesis of 2-oxazolines and 2-oxazoles mediated by ZnI2 and FeCl3 is described. A Lewis acid promoted cyclization of acetylenic amide with various functionalities was well tolerated to give 2-oxazolines and 2-oxazoles in good to excellent yields under mild reaction conditions.