N-Benzyl-2-(2-methoxy-phenyl)-acetamide | 82082-46-0

• 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: N-Benzyl-2-(2-methoxy-phenyl)-acetamide
• 英文别名: N-benzyl-2-(2-methoxyphenyl)acetamide
• CAS: 82082-46-0
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: SUYYCPSFUNZQFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Benzyl-2-(2-methoxy-phenyl)-acetamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到N-苄基-2-(2-羟基苯基)乙酰胺
  参考文献：
  名称：

  New amido derivatives as potential BKCa potassium channel activators. XI

  摘要：

  The vasorelaxing effects of exogenous activators of large-conductance calcium-activated potassium channels (BK channels) can furnish the pharmacological rational basis for the treatment of hypertension and/or other diseases related with an impaired contractility of vessels. Since in previous works some benzanilide derivatives showed BK channel-induced vasorelaxing activity, in this paper we have taken into consideration the introduction of methylene spacer(s) between the amide linker and one or both the aromatic substituents, to evaluate the pharmacological effect caused by these lengthenings and to obtain possible useful information about structure-activity relationships. Overall, the main findings of this work suggest that the introduction of one or two methylene group(s) in the amide linker exerts a negative influence on the BK-opening properties, which can be due to an excessive lengthening of the spacer between the two aromatic rings and/or to further degrees of conformational freedom. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.06.005
• 作为产物：
  描述：

  苄胺 、 邻甲氧基苯乙酰氯 在 TEA 作用下， 以85%的产率得到N-Benzyl-2-(2-methoxy-phenyl)-acetamide
  参考文献：
  名称：

  New amido derivatives as potential BKCa potassium channel activators. XI

  摘要：

  The vasorelaxing effects of exogenous activators of large-conductance calcium-activated potassium channels (BK channels) can furnish the pharmacological rational basis for the treatment of hypertension and/or other diseases related with an impaired contractility of vessels. Since in previous works some benzanilide derivatives showed BK channel-induced vasorelaxing activity, in this paper we have taken into consideration the introduction of methylene spacer(s) between the amide linker and one or both the aromatic substituents, to evaluate the pharmacological effect caused by these lengthenings and to obtain possible useful information about structure-activity relationships. Overall, the main findings of this work suggest that the introduction of one or two methylene group(s) in the amide linker exerts a negative influence on the BK-opening properties, which can be due to an excessive lengthening of the spacer between the two aromatic rings and/or to further degrees of conformational freedom. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.06.005

文献信息

• Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides
  作者：Ningbo Li、Lingxiao Wang、Liting Zhang、Wenjie Zhao、Jie Qiao、Xinhua Xu、Zhiwu Liang

  DOI：10.1002/cctc.201800590

  日期：2018.8.21

  Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air‐stable and water‐tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8

  双（五甲基环戊二烯基）全氟辛烷磺酸锆是一种空气稳定且耐水的路易斯酸。该配合物表现出良好的热稳定性和在极性有机溶剂中的高溶解度。该化合物表现出相对强酸性，具有0.8 <的酸强度何通过羧酸与胺的反应≤3.3，和高的催化效率为N-取代的酰胺的合成，与醇腈的Ritter反应，和胺化含酰胺的醇类。而且，该复合物具有良好的可重用性。该催化体系为合成N-取代的酰胺提供了一种简单而有效的方法。
• Direct amidation of non‐activated carboxylic acid and amine derivatives catalyzed by TiCp ₂ Cl ₂
  作者：Hui Wang、Wei Dong、Zhipeng Hou、Lidan Cheng、Xiufen Li、Longjiang Huang

  DOI：10.1002/aoc.5568

  日期：2020.5

  carboxylic acid and amine derivatives catalyzed by TiCp2Cl2. Arylacetic acid derivatives reacted with different amines to afford the corresponding amides in good to excellent yield except of aniline. Aryl formic acids failed to react with aniline but smoothly reacted with aliphatic amines and benzylamine in moderate to good yield, fatty acids reacting with benzyl and aliphatic amines give amides in good

  本文描述了由TiCp 2 Cl 2催化的非活化羧酸和胺衍生物的温和有效直接酰胺化反应。丁二酸衍生物与不同的胺反应以除苯胺以外的良好至优异的产率提供相应的酰胺。芳基甲酸不能与苯胺反应，但是可以与脂肪胺和苄胺平滑反应，收率中等至良好；脂肪酸与苄基和脂肪胺反应可以得到酰胺，收率很好。手性氨基酸衍生物无需外消旋就可以中等产率转化为酰胺。TiCp 2 Cl 2催化直接酰胺化的可能机理进行了讨论。该催化方法非常适用于低位阻芳基丙烯酸，除苯胺以外的具有不同低位阻胺的脂肪酸的酰胺化，以及芳基甲酸与苄基和脂族胺的酰胺化。
• Potential central nervous system active agents. 2. Synthesis of N-benzylphenylacetamides
  作者：Vincent C. Agwada

  DOI：10.1021/je00030a036

  日期：1982.10
• AGWADA, V. C., J. CHEM. AND ENG. DATA, 1982, 27, N 4, 481-483
  作者：AGWADA, V. C.

  DOI：——

  日期：——
• New amido derivatives as potential BKCa potassium channel activators. XI
  作者：Vincenzo Calderone、Francesca Lidia Fiamingo、Gabriella Amato、Irene Giorgi、Oreste Livi、Alma Martelli、Enrica Martinotti

  DOI：10.1016/j.ejmech.2007.06.005

  日期：2008.4

  The vasorelaxing effects of exogenous activators of large-conductance calcium-activated potassium channels (BK channels) can furnish the pharmacological rational basis for the treatment of hypertension and/or other diseases related with an impaired contractility of vessels. Since in previous works some benzanilide derivatives showed BK channel-induced vasorelaxing activity, in this paper we have taken into consideration the introduction of methylene spacer(s) between the amide linker and one or both the aromatic substituents, to evaluate the pharmacological effect caused by these lengthenings and to obtain possible useful information about structure-activity relationships. Overall, the main findings of this work suggest that the introduction of one or two methylene group(s) in the amide linker exerts a negative influence on the BK-opening properties, which can be due to an excessive lengthening of the spacer between the two aromatic rings and/or to further degrees of conformational freedom. (c) 2007 Elsevier Masson SAS. All rights reserved.