2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxy-N-(4-methoxybenzyl)propanamide | 1414962-83-6

• 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-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxy-N-(4-methoxybenzyl)propanamide
• 英文别名: 2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxy-N-[(4-methoxyphenyl)methyl]propanamide
• CAS: 1414962-83-6
• 化学式: C₁₉H₂₀F₃NO₃
• 分子量: 367.368
• InChiKey: CDUIOAPJMUBDHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溴甲烷 、 2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxy-N-(4-methoxybenzyl)propanamide 在 四丁基溴化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.25h， 生成 N-p-methoxybenzyl-2-methoxy-3,3,3-trifluoro-2-p-ethylphenylpropanamide
  参考文献：
  名称：

  一种新型O-取代三氟内酰胺衍生物的合成、晶体结构、DFT分析及杀菌活性

  摘要：

  摘要 合成了一系列O-取代的三氟atrolactamide衍生物，并通过1H NMR、13C NMR、19F NMR、HRMS和X射线衍射分析对其进行了充分表征。对这些化合物的杀真菌活性进行了评价，结果表明，其中一些化合物对白粉病和稻瘟病菌表现出有效的体外杀真菌活性。使用密度泛函理论计算研究了它们的结构-性能关系。这些化合物之一的 X 射线晶体结构采用具有以下晶胞参数的单斜空间群：a = 24.285 (13) A, b = 9.006 (5) A, c = 9.794 (5) A, β = 92.110 (9)o, V = 2140.6 (19) A3 和 Z = 4。这些实验结果与理论值的比较表明两组数据之间有很好的一致性。

  DOI：

  10.1016/j.molstruc.2016.09.020
• 作为产物：
  描述：

  N-(4-甲氧基苄基)甲酰胺 在 三光气 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxy-N-(4-methoxybenzyl)propanamide
  参考文献：
  名称：

  Novel Ultrasound-Promoted Parallel Synthesis of Trifluoroatrolactamide Library via a One-Pot Passerini/Hydrolysis Reaction Sequence and Their Fungicidal Activities

  摘要：

  An ultrasound-promoted one-pot Passerini/hydrolysis reaction sequence has been developed for the synthesis of trifluoroatrolactamide derivatives using a diverse range of trifluoroacetophenones and isonitriles in acetic acid. Parallel synthesis in a centrifuge tube using a noncontact ultrasonic cell crusher was used in this study as an efficient method for the rapid generation of combinatorial trifluoroatrolactamide libraries, and subsequent biochemical evaluation of the resulting compounds indicated that they possessed excellent broad-spectrum fungicidal activities. N-(4-chlorophenyl)-2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxypropanamide and N-(4-chlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-(4-methoxyphenyl)propanamide, in particular, showed significant fungicidal activities against all of the fungal species tested in the current study.

  DOI：

  10.1021/co400111r

文献信息

• Ultrasound-promoted sterically congested Passerini reactions under solvent-free conditions
  作者：Can Cui、Cong Zhu、Xiu-Jiang Du、Zhi-Peng Wang、Zheng-Ming Li、Wei-Guang Zhao

  DOI：10.1039/c2gc36095k

  日期：——

  A facile, efficient and environmentally-friendly protocol for the synthesis of α-acyloxy amides has been developed by ultrasound-promoted sterically congested Passerini reactions under solvent-free conditions. This method provides several advantages over current reaction methodologies including a simpler work-up procedure, shorter reaction times and higher yields.

  已开发出一种简单、高效且环保的合成α-酰氧基酰胺的程序，该程序在无溶剂条件下利用超声促进的空间拥挤Passerini反应。此方法相比于目前的反应方法具有几个优势，包括更简单的后处理程序、更短的反应时间和更高的产率。
• Novel exocyclic enamides: synthesis and evaluation of the fungicidal activities of 5-methylene-2-(trifluoromethyl)morpholin-3-one derivatives
  作者：Lei Tian、Can Cui、Cong Zhu、Hui-Hui Yang、Jian-Qiang Li、Wei-Guang Zhao

  DOI：10.1039/c5ra20138a

  日期：——

  extensively in the synthesis of natural products and biologically active substances. A facile and efficient protocol has been developed for the synthesis of a series of new 5-methylenemorpholin-3-one derivatives, which are exocyclic enamides, based on the reactions of trifluoroatrolactamides with propargyl bromide in the presence of sodium hydride. The biological evaluation of these compounds showed that

  环外酰胺已广泛用于合成天然产物和生物活性物质。已经开发了一种简便有效的方案，用于在氢化钠存在下，基于三氟环丙酰胺与炔丙基溴的反应，合成一系列新的5-亚甲基吗啉-3-酮衍生物，它们是环外酰胺。这些化合物的生物学评价表明，它们中的一些对稻瘟病菌具有很好的体外杀真菌活性。例如，化合物2d和2e在0.9μgmL -1的浓度下具有50％的杀真菌活性，而对照化合物费南特罗宾在相同的浓度下具有80％的杀真菌活性。
• Synthesis, crystal structure, DFT analysis and fungicidal activity of a novel series O-substituted trifluoroatrolactamide derivatives
  作者：Hui-Hui Yang、Can Cui、Cong Zhu、Jian-Qiang Li、Rui Wu、Lei Tian、Wei-Guang Zhao

  DOI：10.1016/j.molstruc.2016.09.020

  日期：2017.1

  Abstract A series of O-substituted trifluoroatrolactamide derivatives has been synthesized and fully characterized by 1H NMR, 13C NMR, 19F NMR, HRMS and X-ray diffraction analyses. The fungicidal activity of these compounds was evaluated and the results showed that some of them exhibited potent in vitro fungicidal activity against Erysiphe graminis and Pyricularia oryzae. Their structure-property relationships

  摘要 合成了一系列O-取代的三氟atrolactamide衍生物，并通过1H NMR、13C NMR、19F NMR、HRMS和X射线衍射分析对其进行了充分表征。对这些化合物的杀真菌活性进行了评价，结果表明，其中一些化合物对白粉病和稻瘟病菌表现出有效的体外杀真菌活性。使用密度泛函理论计算研究了它们的结构-性能关系。这些化合物之一的 X 射线晶体结构采用具有以下晶胞参数的单斜空间群：a = 24.285 (13) A, b = 9.006 (5) A, c = 9.794 (5) A, β = 92.110 (9)o, V = 2140.6 (19) A3 和 Z = 4。这些实验结果与理论值的比较表明两组数据之间有很好的一致性。
• Novel Ultrasound-Promoted Parallel Synthesis of Trifluoroatrolactamide Library via a One-Pot Passerini/Hydrolysis Reaction Sequence and Their Fungicidal Activities
  作者：Shu-Jing Yu、Cong Zhu、Qiang Bian、Can Cui、Xiu-Jiang Du、Zheng-Ming Li、Wei-Guang Zhao

  DOI：10.1021/co400111r

  日期：2014.1.13

  An ultrasound-promoted one-pot Passerini/hydrolysis reaction sequence has been developed for the synthesis of trifluoroatrolactamide derivatives using a diverse range of trifluoroacetophenones and isonitriles in acetic acid. Parallel synthesis in a centrifuge tube using a noncontact ultrasonic cell crusher was used in this study as an efficient method for the rapid generation of combinatorial trifluoroatrolactamide libraries, and subsequent biochemical evaluation of the resulting compounds indicated that they possessed excellent broad-spectrum fungicidal activities. N-(4-chlorophenyl)-2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxypropanamide and N-(4-chlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-(4-methoxyphenyl)propanamide, in particular, showed significant fungicidal activities against all of the fungal species tested in the current study.