N-m-chlorophenyl-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide | 1456823-27-0

• 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-m-chlorophenyl-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide
• 英文别名: N-(3-chlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide
• CAS: 1456823-27-0
• 化学式: C₁₅H₁₁ClF₃NO₂
• 分子量: 329.706
• InChiKey: VKVOINRVQKKOSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-m-chlorophenyl-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide 、 碘甲烷 在 四丁基溴化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80.6%的产率得到N-(3-chlorophenyl)-3,3,3-trifluoro-2-methoxy-N-methyl-2-phenylpropanamide
  参考文献：
  名称：

  Facile synthesis, crystal structure and antifungal activity of dimethylated trifluoroatrolactamide derivatives

  摘要：

  使用 CH3I 作为甲基化剂，从 α-羟基乙酰胺合成了一系列新型取代的 3,3,3-三氟-2-甲氧基-N-甲基-N,2-二苯基丙酰胺。通过 1H NMR、13C NMR、19F NMR 和 HRMS X 射线分析对其化学结构进行了表征。二甲基三氟阿托拉酰胺表现出适度的抗真菌活性。

  DOI：

  10.1007/s11164-016-2767-5
• 作为产物：
  描述：

  N-(3-氯苯基)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 N-m-chlorophenyl-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide
  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

• 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。
• 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.
• Facile synthesis, crystal structure and antifungal activity of dimethylated trifluoroatrolactamide derivatives
  作者：Hui-Hui Yang、Cong Zhu、Can Cui、Jian-Qiang Li、Wei-Guang Zhao、Xing-Hai Liu

  DOI：10.1007/s11164-016-2767-5

  日期：2017.4

  A series of novel substituted 3,3,3-trifluoro-2-methoxy-N-methyl-N,2-diphenylpropanamides were synthesized from α-hydroxyacetamide using CH3I as the methylating agent. Their chemical structures were characterized by 1H NMR, 13C NMR, 19F NMR, and HRMS X-ray analysis. The dimethylated trifluoroatrolactamide exhibited moderate antifungal activity.

  使用 CH3I 作为甲基化剂，从 α-羟基乙酰胺合成了一系列新型取代的 3,3,3-三氟-2-甲氧基-N-甲基-N,2-二苯基丙酰胺。通过 1H NMR、13C NMR、19F NMR 和 HRMS X 射线分析对其化学结构进行了表征。二甲基三氟阿托拉酰胺表现出适度的抗真菌活性。