N-(1-hydroxy-2,2,2-trichloroethyl)-2,4-dichlorobenzamide | 103029-72-7

• 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-(1-hydroxy-2,2,2-trichloroethyl)-2,4-dichlorobenzamide
• 英文别名: 2,4-Dichlor-benzoesaeure-(2,2,2-trichlor-1-hydroxy-ethylamid)；2,4-dichloro-N-(2,2,2-trichloro-1-hydroxyethyl)benzamide
• CAS: 103029-72-7
• 化学式: C₉H₆Cl₅NO₂
• 分子量: 337.417
• InChiKey: PNAIHZUWUMSRHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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-(1-hydroxy-2,2,2-trichloroethyl)-2,4-dichlorobenzamide 在 氯化亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  有机磷化合物作为潜在的杀菌剂。第 V.1 部分一些新型 N,N,N',N'-四甲基-N''-(1-取代-2,2,2-三氯乙基)磷酸三酰胺的制备和性能

  摘要：

  摘要 制备了一系列N,N,N',N'-四甲基-N''-(1-取代-2,2,2-三氯乙基)磷酰胺，其中1-取代基为酰胺基NHCOR (R = H, Me, CH2Cl, CCl3, 2,4-dichlo-rophenyl, 2-methylfuran-3-yl, 5,6-dihydro-2-methyl-1,4-oxathiin-3-yl), 烷氧基基团 (OMe、OEt、OBu、OC12H25) 或取代的乙酰胺基 (NHCOCH2Y)，其中 Y 是三唑基、N,N-二-甲基二硫代氨基甲酸、N,N-二乙基二硫代氨基甲酸、二乙基黄原、二乙氧基硫代磷酰硫基或十二烷硫基。当在体外以 300 ppm 对一系列生物体进行测试时，这些化合物作为杀真菌剂的活性通常较低。然而，某些化合物（1-甲酰胺基、1-乙酰胺基和 1-氯乙酰胺基衍生物）在体内表现出参考杀菌剂（胍丁胺）的 55-77% 的活性，当以 400

  DOI：

  10.1080/10426509608029647
• 作为产物：
  描述：

  水合氯醛 、 2,4-二氯苯甲酰胺 以 neat (no solvent) 为溶剂， 以88 %的产率得到N-(1-hydroxy-2,2,2-trichloroethyl)-2,4-dichlorobenzamide
  参考文献：
  名称：

  基于N-（2,2,2-三氯-1-（3-R-硫脲基）乙基）甲酰胺的6-R-N-芳基-4-（三氯甲基）-4H-1,3,5-噁二嗪-2-胺的合成：其光谱特性和分子结构

  摘要：

  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。

  DOI：

  10.1002/jhet.4870

文献信息

• Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides
  作者：Pavlo V. Zadorozhnii、Ihor O. Pokotylo、Vadym V. Kiselev、Aleksandr V. Kharchenko、Oxana V. Okhtina

  DOI：10.1515/hc-2019-0020

  日期：2019.11.28

  Based on readily available N-(2,2,2-trichloro-1-hydroxyethyl)carboxamides, N-(2,2,2-trichloro-1-(3-(3-mercapto-4H-1,2,4-triazol-4-yl)thioureido)ethyl) carboxamides, dehydrosulfurization–under the influence of excess HgO–led to the formation of N-(1-([1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides. The reaction was carried out in boiling glacial acetic acid for 1-1.5 hours. The cyclization products were obtained in 42-62% yields and easily isolated from the reaction mixture. The structure of all synthesized compounds was confirmed by complex spectral studies.

  基于易得的N-(2,2,2-三氯-1-羟乙基)羧酰胺，N-(2,2,2-三氯-1-(3-(3-巯基-4H-1,2,4-三唑-4-基)硫脲基)乙基)羧酰胺，通过过量HgO的脱硫化作用，在沸腾的冰乙酸中反应1-1.5小时，形成了N-(1-([1,2,4]三唑[3,4-b][1,3,4]噻二唑-6-基氨基)-2,2,2-三氯乙基)羧酰胺。环化产物以42-62%的产率得到，并且可以很容易地从反应混合物中分离。所有合成化合物的结构都通过复杂的光谱研究得到了确认。

• 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.
• ORGANOPHOSPHORUS COMPOUNDS AS POTENTIAL FUNGICIDES. PART V.¹ THE PREPARATION AND PROPERTIES OF SOME NOVEL N,N,N',N'-TETRAMETHYL-N''-(1-SUBSTITUTED-2,2,2-TRICHLOROETHYL) PHOSPHORIC TRIAMIDES
  作者：Harry R. Hudson、Christakis N. Mavrommatis、Max Pianka

  DOI：10.1080/10426509608029647

  日期：1996.1.1

  Abstract A series of N,N,N',N'-tetramethyl-N''-(1-substituted-2,2,2-trichloroethyl)phosphoric triamides has been prepared in which the 1-substituent is an amido group, NHCOR (R = H, Me, CH2Cl, CCl3, 2,4-dichlo-rophenyl, 2-methylfuran-3-yl, 5,6-dihydro-2-methyl-1,4-oxathiin-3-yl), an alkoxy group (OMe, OEt, OBu, OC12H25), or a substituted acetamido group (NHCOCH2Y), in which Y is triazolyl, N,N-di-methyldithiocarbamato

  摘要 制备了一系列N,N,N',N'-四甲基-N''-(1-取代-2,2,2-三氯乙基)磷酰胺，其中1-取代基为酰胺基NHCOR (R = H, Me, CH2Cl, CCl3, 2,4-dichlo-rophenyl, 2-methylfuran-3-yl, 5,6-dihydro-2-methyl-1,4-oxathiin-3-yl), 烷氧基基团 (OMe、OEt、OBu、OC12H25) 或取代的乙酰胺基 (NHCOCH2Y)，其中 Y 是三唑基、N,N-二-甲基二硫代氨基甲酸、N,N-二乙基二硫代氨基甲酸、二乙基黄原、二乙氧基硫代磷酰硫基或十二烷硫基。当在体外以 300 ppm 对一系列生物体进行测试时，这些化合物作为杀真菌剂的活性通常较低。然而，某些化合物（1-甲酰胺基、1-乙酰胺基和 1-氯乙酰胺基衍生物）在体内表现出参考杀菌剂（胍丁胺）的 55-77% 的活性，当以 400
• 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。