methyl 4-(N-methyl-3-phenylpropiolamido)benzoate | 1015230-89-3

• 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: methyl 4-(N-methyl-3-phenylpropiolamido)benzoate
• CAS: 1015230-89-3
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: WEAVCZDAOGVLAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(N-methyl-3-phenylpropiolamido)benzoate 在 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate 作用下， 以 二甲基亚砜 为溶剂， 以60 %的产率得到
  参考文献：
  名称：

  电还原和氢键活化的合并用于自由基 Smiles 重排

  摘要：

  在较低负电势下化学键的还原活化为高官能团耐受性和选择性奠定了基础，是有机电合成的中心主题之一。沿着这条线，我们报告了通过将电还原与氢键激活相结合的双激活模式的设计。作为原理证明， N-苯基丙酰胺的还原电位正移了 218 mV。通过该策略，无需外部自由基前体和预官能化步骤即可完成N-芳基丙酰胺的自由基 Smiles 重排。 [DBU][HOAc]是一种易于获得的离子液体，首次被用作氢键供体和支持电解质。

  DOI：

  10.1039/d4sc02821j
• 作为产物：
  描述：

  对溴苯甲酸甲酯 、 N-methyl-3-phenylpropiolamide 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 生成 methyl 4-(N-methyl-3-phenylpropiolamido)benzoate
  参考文献：
  名称：

  钯催化的多米诺骨牌N-芳基化/卡巴钯化/ CH功能化：3-（二芳基亚甲基）氧吲哚的三组分合成

  摘要：

  已经开发了3-（二芳基亚甲基）吲哚-2-酮的钯催化的三组分合成。以一锅方式实现了一系列分子间N-芳基化/分子间碳pal化/ C–H活化/ C–C键形成，从而允许通过三个不同的催化作用构建一个C–N键和两个C–C键周期。

  DOI：

  10.1016/j.tetlet.2009.03.086

文献信息

• Palladium-Catalyzed Oxidative Carboacetoxylation of Activated Alkynes with Amino Acids
  作者：Shi Tang、Qing-Lan Li、Dong Zhou、Xin-Mei Tang、Shu-Hua Li

  DOI：10.1080/00397911.2013.835422

  日期：2014.3.4

  A palladium-catalyzed intramolecular oxidative carboacetoxylation reaction of alkynes with various amino acids has been demonstrated for the first time, forming pharmaceutically important 3-methyleneindolin-2-one. In the presence of Pd(OAc)(2) and ArI(OAc)(2), N-arylpropiolamides underwent tandem acetoxypalladation/C-H functionalization reactions with various Boc-amino acids to form corresponding methyleneindolin-2-ones bearing amino acid motifs in moderate to excellent yields. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• Synthesis of (2-Oxoindolin-3-ylidene)methyl Acetates Involving a C−H Functionalization Process
  作者：Shi Tang、Peng Peng、Zhi-Qiang Wang、Bo-Xiao Tang、Chen-Liang Deng、Jin-Heng Li、Ping Zhong、Nai-Xing Wang

  DOI：10.1021/ol8006315

  日期：2008.5.1

  [GRAPHICS]A novel palladium-catalyzed oxidative C-H functionalization protocol for the synthesis of (2-oxoindolin-3-ylidene)methyl acetates has been developed. In the presence of Pd(OAC)(2) and Phl(OAC)(2), a variety of N-arylpropiolamides underwent the C-H functionalization reaction with acids to afford the corresponding (E)-(2-oxoindolin-3-ylidene)methyl acetates selectively in moderate to excellent yields.
• Sequential Intermolecular Aminopalladation/<i>ortho</i>-Arene C−H Activation Reactions of <i>N</i>-Phenylpropiolamides with Phthalimide
  作者：Shi Tang、Peng、Shao-Feng Pi、Yun Liang、Nai-Xing Wang、Jin-Heng Li

  DOI：10.1021/ol800080w

  日期：2008.3.1

  A novel palladium-catalyzed intermolecular aminopalladation/C-H activation method for selectively synthesizing (E)-(2-oxindolin-3-ylidene)phthalimides has been developed. In the presence of Pd(OAc)(2) and Phl(OAc)(2), alkynes were difunctionalized with a phthalimide and an arene Sp(2) C-H bond to selectively synthesize (E)-(2-oxoindolin-3-ylidene)phthalimides, which products are of great potential pharmaceutical value products in many major therapeutic areas, such as oncology, inflammation, neurology, immunology, and endocrinology. To the best of our knowledge, the reaction serves as the first example of intermolecular aminopalladation/C-H activation reactions of alkynes.