2-hydroxy-N-[(2-methoxyphenyl)methyl]benzamide | 930471-98-0

• 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: 2-hydroxy-N-[(2-methoxyphenyl)methyl]benzamide
• CAS: 930471-98-0
• 化学式: C₁₅H₁₅NO₃
• mdl: MFCD09322256
• 分子量: 257.289
• InChiKey: CIKWAJVEIUUWSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-[(2-methoxyphenyl)methyl]benzamide 在 叔丁基过氧化氢 、 caesium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以79%的产率得到2-hydroxy-2-(2-methoxyphenyl)-2,3-dihydro-4H-benzo-[e][1,3]oxazin-4-one
  参考文献：
  名称：

  与酰胺氮原子相邻的C（sp 3）H键的分子内官能化：2-羟基-苯并恶嗪酮衍生物的无金属合成

  摘要：

  一个分子内的C（sp 3）H键功能与酰胺氮原子相邻已成功开发了在环境友好的条件下合成2-羟基苯并恶嗪酮衍生物。该方法无金属催化剂，底物范围宽，收率高。此外，在反应过程中还提出了自由基机理。另外，大多数目标化合物对MCF-7和Hela细胞表现出有效的抗增殖活性。

  DOI：

  10.1016/j.tet.2017.09.001
• 作为产物：
  描述：

  2-甲氧基-N-(2-甲氧基苄基)苯甲酰胺 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到2-hydroxy-N-[(2-methoxyphenyl)methyl]benzamide
  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

• 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.
• Intramolecular functionalization of C(sp 3 ) H bonds adjacent to an amide nitrogen atom: Metal-free synthesis of 2-hydroxy-benzoxazinone derivatives
  作者：Biao Gao、Kaili Chen、Xiaoling Bi、Jinxin Wang

  DOI：10.1016/j.tet.2017.09.001

  日期：2017.12

  An intramolecular C(sp3)H bond functionalization adjacent to an amide nitrogen atom was successfully developed for synthesis of 2-hydroxybenzoxazinone derivatives under environment-friendly conditions. The method featured no metal catalyst, broad substrate scopes and high yields. Besides, a radical mechanism was proposed in the reaction process. Additionally, most of target compounds exhibited potent

  一个分子内的C（sp 3）H键功能与酰胺氮原子相邻已成功开发了在环境友好的条件下合成2-羟基苯并恶嗪酮衍生物。该方法无金属催化剂，底物范围宽，收率高。此外，在反应过程中还提出了自由基机理。另外，大多数目标化合物对MCF-7和Hela细胞表现出有效的抗增殖活性。