N-(2-Hydroxyphenyl)-3-methylbenzamide

• 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-(2-Hydroxyphenyl)-3-methylbenzamide
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: OTUMFOHWIGPQKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-Hydroxyphenyl)-3-methylbenzamide 在 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 23.0h， 以90%的产率得到2-(3-甲基苯基)-1,3-苯并恶唑
  参考文献：
  名称：

  以PPh3-DDQ为脱水剂方便合成2-恶唑啉和2-苯并恶唑

  摘要：

  用三苯基膦-2,3-二氯-5,6-二氰基苯并醌（PPh 3 -DDQ）作为脱水和活化试剂分别从酰基氨基醇和酰基氨基苯酚分别以高收率合成了2-恶唑啉和2-苯并恶唑。该合成在中性条件下完成。

  DOI：

  10.1002/cjoc.201190190
• 作为产物：
  描述：

  2-氨基苯酚 、 间甲基苯甲酸 在 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 丙酮 为溶剂， 以74 %的产率得到N-(2-Hydroxyphenyl)-3-methylbenzamide
  参考文献：
  名称：

  作为选择性 COX-2 抑制剂的白藜芦醇酰胺衍生物的合成及生物学评价

  摘要：

  选择性 COX-2 抑制剂已被认为是 tNSAID 的可靠替代品，但由于存在心脏病发作和中风的风险，其中大部分已退出市场。因此，迫切需要开发一种高效低毒的新型选择性COX-2抑制剂。受白藜芦醇心血管保护和抗炎活性的启发，我们合成了 38 种白藜芦醇酰胺衍生物并评估了它们的 COX-1/COX-2 抑制活性。化合物8a、6a、8c和13c显示出对 COX-2 的重要抑制活性 (IC 50 = 0.42–2.54 μM)，具有明确的选择性 (SI = 48–83)。分子对接研究表明，这些化合物部分进入 COX-2 活性位点的 2° 口袋，并与负责 COX-2 选择性的氨基酸残基相互作用，其方向和结合相互作用与罗非昔布相似。进一步对这些活性化合物进行体内抗炎活性评价，发现化合物8a无胃溃疡毒性，50 mg/kg 3次口服均显示出明显的抗炎作用（水肿抑制45.95%），值得重视进一步研究。此外，化

  DOI：

  10.1016/j.cbi.2023.110522

文献信息

• A Convenient Synthesis of 2-Oxazolines and 2-Benoxazoles with PPh3-DDQ as the Dehydrating Reagent
  作者：Quancai Xu、Zhengning Li、Huiying Chen

  DOI：10.1002/cjoc.201190190

  日期：2011.5

  2‐benoxazoles were synthesized in high yields from acylamino alcohols and acylamino‐ phenols, respectively, with triphenylphosphine‐2,3‐dichloro‐5,6‐dicyanobenzoquinone (PPh3‐DDQ) as the dehydrating and activating reagent. The synthesis was accomplished under neutral conditions.

  用三苯基膦-2,3-二氯-5,6-二氰基苯并醌（PPh 3 -DDQ）作为脱水和活化试剂分别从酰基氨基醇和酰基氨基苯酚分别以高收率合成了2-恶唑啉和2-苯并恶唑。该合成在中性条件下完成。
• Multicomponent Synthesis of Isoindolinone Frameworks via Rh^III-Catalysed in situ Directing Group-Assisted Tandem Oxidative Olefination/Michael Addition
  作者：Liang Wang、Xi Liu、Jian-biao Liu、Jun Shen、Qun Chen、Ming-yang He

  DOI：10.1002/asia.201800120

  日期：2018.4.4

  A RhIII‐catalysed three‐component synthesis of isoindolinone frameworks via direct assembly of benzoyl chlorides, o‐aminophenols and activated alkenes has been developed. The process involves in situ generation of o‐aminophenol (OAP)‐based bidentate directing group (DG), RhIII‐catalysed tandem ortho C−H olefination and subsequent cyclization via aza‐Michael addition. This protocol exhibits good chemoselectivity

  通过苯甲酰氯，邻氨基苯酚和活性烯烃的直接组装，Rh III催化的异吲哚啉酮骨架的三组分合成。该过程涉及原位生成基于邻氨基苯酚（OAP）的双齿指导基团（DG），Rh III催化的串联邻位C-H烯化反应以及随后通过氮杂-Michael加成反应的环化反应。该协议显示出良好的化学选择性和官能团耐受性。计算研究表明，N-芳基环上羟基的存在可以增强反应的化学选择性。
• Supported Pd-catalyzed ring opening and chemoselective aminocarbonylative coupling of benzoxazoles with aryl iodides
  作者：Pushkar Mehara、Ajay Kumar Sharma、Ashish Kumar、Poonam Sharma、Pralay Das

  DOI：10.1039/d4cy00070f

  日期：——

  A tandem approach using polystyrene supported Pd catalyzed ring opening aminocarbonylative coupling of benzoxazoles with aryl iodides has been developed for the synthesis of N-(2-hydroxyphenyl)benzamides using solid oxalic acid as the CO source.

  以固体草酸为 CO 源，开发了一种串联方法，利用聚苯乙烯支撑的钯催化苯并恶唑与芳基碘化物的开环氨基羰基偶联合成 N-(2-羟基苯基)苯甲酰胺。
• Biochemical and Structural Evaluation of Highly Selective 2-Arylbenzoxazole-Based Transthyretin Amyloidogenesis Inhibitors
  作者：Steven M. Johnson、Stephen Connelly、Ian A. Wilson、Jeffery W. Kelly

  DOI：10.1021/jm0708735

  日期：2008.1.1

  To develop potent transthyretin (TTR) amyloidogenesis inhibitors that also display high binding selectivity in blood, it proves useful to systematically optimize each of the three substructural elements that comprise a typical inhibitor: the two aryl rings and the linker joining them. In the first study, described herein, structural modifications to one aryl ring were evaluated by screening a library of 2-arylbenzoxazoles bearing thyroid hormone-like aryl substituents on the 2-aryl ring. Several potent and highly selective amyloidogenesis inhibitors were identified that exhibit minimal thyroid hormone nuclear receptor and COX-1 binding. High resolution crystal structures (1.3-1.5 angstrom) of three inhibitors (2f, 4f, and 4d) in complex with TTR were obtained to characterize their binding orientation. Collectively, the results demonstrate that thyroid hormone-like substitution patterns on one aryl ring lead to potent and highly selective TTR amyloidogenesis inhibitors that lack undesirable thyroid hormone receptor or COX-1 binding.
• Synthesis, antimicrobial, and QSAR studies of substituted benzamides
  作者：Anil Kumar、Balasubramanian Narasimhan、Devinder Kumar

  DOI：10.1016/j.bmc.2007.03.074

  日期：2007.6

  A series of new substituted benzamides were synthesized and tested in vitro for their antibacterial activity against Grampositive and Gram-negative bacteria and as well for antifungal activity. The compounds 8i and 9 showed better activity among the different benzamides synthesized. The structural characteristics governing antibacterial activities of substituted benzamides were studied using QSAR methodology. The results showed that the antimicrobial activity could be modeled using the topological descriptors, molecular connectivity indices ((2)chi(v) and (2)chi) and Kiers shape index (kappa alpha(1)). The low residual activity and high cross-validated r(2) values (r(cv)(2)) observed indicated the predictive ability of the developed QSAR models. (C) 2007 Elsevier Ltd. All rights reserved.