N-(2,2,2-trichloro-1-hydroxyethyl)trimethylacetamide | 16535-65-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,2,2-trichloro-1-hydroxyethyl)trimethylacetamide
• 英文别名: N-(2,2,2-trichlor-1-hydroxyethyl)trimethylacetamid；NoName_659；2,2-dimethyl-N-(2,2,2-trichloro-1-hydroxyethyl)propanamide
• CAS: 16535-65-2
• 化学式: C₇H₁₂Cl₃NO₂
• 分子量: 248.537
• InChiKey: UQHHXDSDEGGFFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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-(2,2,2-trichloro-1-hydroxyethyl)trimethylacetamide 在 sodium hydrogen sulfide 、 氯化亚砜 作用下， 以 苯 为溶剂， 生成 [2-tert-butyl-5-(methylthio)-1,3-oxazol-4-yl](triphenyl)phosphonium iodide
  参考文献：
  名称：

  In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate Acinetobacter baumannii

  摘要：

  AbstractQSAR analysis of a set of previously synthesized phosphonium ionic liquids (PILs) tested against Gram‐negative multidrug‐resistant clinical isolate Acinetobacter baumannii was done using the Online Chemical Modeling Environment (OCHEM). To overcome the problem of overfitting due to descriptor selection, fivefold cross‐validation with variable selection in each step of the model development was applied. The predictive ability of the classification models was tested by cross‐validation, giving balanced accuracies (BA) of 76%–82%. The validation of the models using an external test set proved that the models can be used to predict the activity of newly designed compounds with a reasonable accuracy within the applicability domain (BA = 83%–89%). The models were applied to screen a virtual chemical library with expected activity of compounds against MDR Acinetobacter baumannii. The eighteen most promising compounds were identified, synthesized, and tested. Biological testing of compounds was performed using the disk diffusion method in Mueller‐Hinton agar. All tested molecules demonstrated high anti‐A. baumannii activity and different toxicity levels. The developed classification SAR models are freely available online at http://ochem.eu/article/113921 and could be used by scientists for design of new more effective antibiotics.

  DOI：

  10.1111/cbdd.13678
• 作为产物：
  描述：

  水合氯醛 、 三甲基乙酰胺 以90%的产率得到N-(2,2,2-trichloro-1-hydroxyethyl)trimethylacetamide
  参考文献：
  名称：

  N-（2,2-二氯乙烯基）酰胺的电化学生成

  摘要：

  已经建立了一种方便的合成N-（2,2-二氯乙烯基）酰胺的方法。用五氯化磷处理氯乙酰胺可提供高产率的N-（1,2,2,2-四氯乙基）酰胺，其电化学还原反应可标题化合物以公平至定量的产率获得。与以前报道的程序相比，这种方法具有更高的效率和多功能性。

  DOI：

  10.1016/s0040-4020(01)00434-3

文献信息

• 10.1002/jhet.4870
  作者：Lomynoha, Yelyzaveta R.、Zadorozhnii, Pavlo V.、Kiselev, Vadym V.、Kharchenko, Aleksandr V.

  DOI：10.1002/jhet.4870

  日期：——

  report the synthesis of a series of new 4H-1,3,5-oxadiazine derivatives. The method of their production is based on the dehydrosulfurization reaction of N-(2,2,2-trichloro-1-(3-R-thioureido)ethyl)carboxamides under the action of a mixture of iodine and triethylamine in DMF. A possible reaction mechanism has been proposed. The target products have been obtained in 58%–75% yield. The structure of the obtained

  在这项工作中，我们报道了一系列新的 4 H-1,3,5-噁二嗪衍生物的合成。其生产方法基于 N-（2,2,2-三氯-1-（3-R-硫脲基）乙基）甲酰胺在 DMF 中碘和三乙胺混合物作用下的脱氢硫化反应。已经提出了一种可能的反应机制。以 58%–75% 的收率获得目标产品。所得化合物的结构已通过 1H、13C NMR、IR 光谱数据和对 6-（叔丁基）-N-苯基-4-（三氯甲基）-4 H-1,3,5-噁二嗪-2-胺进行的 X 射线衍射分析得到证实。
• Kashik,T.V. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 1643 - 1647
  作者：Kashik,T.V. et al.

  DOI：——

  日期：——
• Concise and regioselective synthesis of 5H-imidazo[1,2-e][1,3,5]triazepines
  作者：Bohdan A. Demydchuk、Oleksandr A. Mykhalchenko、Eduard B. Rusanov、Viktoriia S. Moskvina、and Volodymyr S. Brovarets s

  DOI：10.24820/ark.5550190.p011.689

  日期：——
• Electrochemical generation of N-(2,2-dichlorovinyl)amides
  作者：Antonio Guirado、Raquel Andreu、Alfredo Cerezo、Jesús Gálvez

  DOI：10.1016/s0040-4020(01)00434-3

  日期：2001.6

  A convenient method for the synthesis of N-(2,2-dichlorovinyl)amides has been established. Treatment of chloralamides with phosphorus pentachloride provides N-(1,2,2,2-tetrachloroethyl)amides in high yields whose electrochemical reduction leads to the title compounds in fair to quantitative yields. This approach exhibits superior efficiency and versatility than previously reported procedures.

  已经建立了一种方便的合成N-（2,2-二氯乙烯基）酰胺的方法。用五氯化磷处理氯乙酰胺可提供高产率的N-（1,2,2,2-四氯乙基）酰胺，其电化学还原反应可标题化合物以公平至定量的产率获得。与以前报道的程序相比，这种方法具有更高的效率和多功能性。
• In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate <i>Acinetobacter baumannii</i>
  作者：Maria M. Trush、Vasyl Kovalishyn、Diana Hodyna、Olexandr V. Golovchenko、Svitlana Chumachenko、Igor V. Tetko、Volodymyr S. Brovarets、Larysa Metelytsia

  DOI：10.1111/cbdd.13678

  日期：2020.6

  AbstractQSAR analysis of a set of previously synthesized phosphonium ionic liquids (PILs) tested against Gram‐negative multidrug‐resistant clinical isolate Acinetobacter baumannii was done using the Online Chemical Modeling Environment (OCHEM). To overcome the problem of overfitting due to descriptor selection, fivefold cross‐validation with variable selection in each step of the model development was applied. The predictive ability of the classification models was tested by cross‐validation, giving balanced accuracies (BA) of 76%–82%. The validation of the models using an external test set proved that the models can be used to predict the activity of newly designed compounds with a reasonable accuracy within the applicability domain (BA = 83%–89%). The models were applied to screen a virtual chemical library with expected activity of compounds against MDR Acinetobacter baumannii. The eighteen most promising compounds were identified, synthesized, and tested. Biological testing of compounds was performed using the disk diffusion method in Mueller‐Hinton agar. All tested molecules demonstrated high anti‐A. baumannii activity and different toxicity levels. The developed classification SAR models are freely available online at http://ochem.eu/article/113921 and could be used by scientists for design of new more effective antibiotics.