N-(3,4-dimethoxyphenyl)-2-phenylacetamide | 169120-65-4

• 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: N-(3,4-dimethoxyphenyl)-2-phenylacetamide
• 英文别名: N-(3,4-dimethoxyphenyl)benzeneacetamide；phenyl-acetic acid-(3,4-dimethoxy-anilide)；Phenyl-essigsaeure-(3,4-dimethoxy-anilid)
• CAS: 169120-65-4
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: DJLKJMRCOASVMD-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C(Solv: ethanol (64-17-5))
• 沸点：
  469.2±45.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxyphenyl)-2-phenylacetamide 在 三氟甲磺酸 、 5% palladium on Al₂O₃ 作用下， 反应 4.0h， 以87%的产率得到N,N’-(4,4’5,5’-tetramethoxy[1,1’-biphenyl]-2,2’-diyl)bisbenzeneacetamide
  参考文献：
  名称：

  异质金属催化剂对苯甲酸酯的需氧氧化均偶联反应

  摘要：

  我们已经开发了在氧气氛下二甲氧基苯胺的非均相催化氧化均偶联反应。所得的均二聚体可用于杂环的构建，证明了多相金属催化剂的潜力。

  DOI：

  10.1016/j.tetlet.2017.01.075
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 、 五氯化磷 作用下， 生成 N-(3,4-dimethoxyphenyl)-2-phenylacetamide
  参考文献：
  名称：

  Farooq; Rahman; Ilyas, Chemische Berichte, 1959, vol. 92, p. 2555,2558

  摘要：

  DOI：

文献信息

• Tyrphostins. 5. Potent Inhibitors of Platelet-Derived Growth Factor Receptor Tyrosine Kinase:  Structure−Activity Relationships in Quinoxalines, Quinolines, and Indole Tyrphostins
  作者：Aviv Gazit、Harald App、Gerald McMahon、Jefferey Chen、Alexander Levitzki、Frank D. Bohmer

  DOI：10.1021/jm950727b

  日期：1996.1.1

  3-arylquinoxalines were prepared and tested for inhibition of platelet-derived growth factor receptor tyrosine kinase (PDGF-RTK) activity. The potency of the inhibitors was found to be quinoxalines > quinolines > indoles. Lipophilic groups (methyl, methoxy) in the 6 and 7 positions and phenyl at the 3 position of quinoxalines and quinolines were essential for potency, in contrast to the hydrophilic catechol

  制备了一系列3-吲哚丙烯腈酪氨酸酪蛋白，2-氯-3-苯基喹啉和3-芳基喹喔啉，并测试了其对血小板衍生的生长因子受体酪氨酸激酶（PDGF-RTK）活性的抑制作用。发现抑制剂的效力为喹喔啉>喹啉>吲哚。喹喔啉和喹啉在6和7位上的亲脂基团（甲基，甲氧基）和3位上的苯基对于效价至关重要，而酪蛋白中的亲水邻苯二酚基团在不同位点具有抑制EGFR激酶活性。抑制剂对PDGF具有选择性，对EGF受体和HER-2 / c-ErbB-2受体无活性。
• Hydrative syntheses of amides from alkynes catalyzed by an Au(I) complex containing pyridyl-functionalized NHC ligand
  作者：Kuldeep Singh、Nilay Kumar Pal、Chirajyoti Guha、Jitendra K. Bera

  DOI：10.1016/j.jorganchem.2019.02.011

  日期：2019.4

  the ligand scaffold is synthesized and its catalytic efficacy for the direct synthesis of the amide from alkyne and sodium azide in acidic water is evaluated. Catalyst 1 readily converts a wide range of internal and terminal alkynes to the corresponding amides with low catalyst loading in TFA/DCE (2 mL, 1:1 v/v) at room temperature in short reaction time (2 h) and without the use of Ag(I) additive. A

  合成了在配体骨架上带有吡啶基的Au（I）-NHC络合物[L 1 AuBr]（1），并评估了其在酸性水中由炔烃和叠氮化钠直接合成酰胺的催化效果。催化剂1在TFA / DCE（2 mL，1：1 v / v）中催化剂负载量低的情况下，很容易将各种内部和末端炔烃转化为相应的酰胺）在室温下以较短的反应时间（2 h）进行，并且不使用Ag（I）添加剂。不含吡啶基片段的相关催化剂显示出明显较低的活性，说明了启动子配体对水活化的作用。机理研究表明，炔烃最初会水合成酮，然后进行Schmidt反应生成酰胺。
• One-step synthesis of 4-methyl-2-substituted quinazoline-3-oxides via polyphosphoric acid catalyzed acylation of electron-rich anilides with nitroethane
  作者：Igor Yu Grishin、Alexander V. Aksenov、Nicolai A. Aksenov、Yuriy I. Grishin、Alexander V. Leontiev、Dmitrii A. Aksenov

  DOI：10.1016/j.tet.2023.133784

  日期：2024.1

  A diverse set of 4-methyl-2-substituted quinazoline-3-oxides has been prepared using polyphosphoric acid both as a reaction medium and a Brønsted-acid catalyst. The reaction proceeds in a domino fashion via the formation of a corresponding oxime followed by exo-trig cyclization and elimination of a water molecule which leads, ultimately, to the target N-oxide heterocycles.

  使用多磷酸作为反应介质和布朗斯台德酸催化剂，制备了多种 4-甲基-2-取代的喹唑啉-3-氧化物。该反应以多米诺骨牌方式进行通过形成相应的肟，然后形成exo-trig 环化并消除水分子，最终形成目标N-氧化物杂环。
• Treatment of platelet derived growth factor related disorders such as cancers using inhibitors of platelet derived growth receptor
  申请人：Sugen, Inc.

  公开号：EP1000617A2

  公开（公告）日：2000-05-17

  The present invention concerns compounds which can inhibit platelet derived growth factor receptor (PDGF-R) activity, preferably such compounds also inhibit the activity of other members of the PDGF-R super family and are selective for members of the PDGF-R super family. The PDGF-R super family includes PDGF-R and PDGF-R related kinases Flt, and KDR. The featured compounds are active on cell cultures to reduce the activity of the PDGF-R and preferably one or more PDGF-R related kinases. An example of a featured compound, A10 (see Figure 1A), and its ability to inhibit growth of tumor cells in vivo is described below. Using the present application as guide, other compounds able to inhibit PDGF-R and preferably Flt and/or KDR can be obtained. Such compounds are preferably used to treat patients suffering from cell proliferative disorders characterized by inappropriate PDGF-R activity.

  本发明涉及可抑制血小板衍生生长因子受体（PDGF-R）活性的化合物，最好此类化合物还能抑制 PDGF-R 超家族其他成员的活性，并对 PDGF-R 超家族成员具有选择性。PDGF-R 超家族包括 PDGF-R、PDGF-R 相关激酶 Flt 和 KDR。特色化合物对细胞培养物具有活性，可降低 PDGF-R，最好是一种或多种 PDGF-R 相关激酶的活性。下面将举例说明特色化合物 A10（见图 1A）及其抑制体内肿瘤细胞生长的能力。以本申请为指导，可以获得其他能够抑制 PDGF-R，最好是 Flt 和/或 KDR 的化合物。此类化合物最好用于治疗以不适当的 PDGF-R 活性为特征的细胞增殖性疾病患者。
• Dithiocarbamate and DBU-promoted amide bond formation under microwave condition
  作者：Katari Naresh Kumar、Kintali Sreeramamurthy、Sadananda Palle、Khagga Mukkanti、Parthasarathi Das

  DOI：10.1016/j.tetlet.2009.11.127

  日期：2010.2

  Dithiocarbamate and DBU-promoted amide bond formation under microwave condition has been reported. The versatility of this synthetic protocol has been demonstrated with various carboxylic acids and different dithiocarbamates. The products thus obtained have been characterized by mp, IR, H-1 NMR, and mass spectroscopy. (C) 2009 Elsevier Ltd. All rights reserved.