4-acetylbenzothioamide | 2362-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetylbenzothioamide
• 英文别名: 4-Thiocarbamoyl-acetophenon；p-Acetyl thiobenzamide；p-Acetyl-thiobenzamid；p-Acetylthiobenzamid；4-Acetylbenzenecarbothioamide
• CAS: 2362-65-4
• 化学式: C₉H₉NOS
• 分子量: 179.243
• InChiKey: ABEKALYJEDVXTN-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  333.4±44.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-acetylbenzothioamide 在 吡啶 作用下， 以 甲苯 、 xylene 为溶剂， 反应 3.0h， 生成 6-(4-Acetyl-phenyl)-[1,3,5]thiadiazine-2,4-dione
  参考文献：
  名称：

  Synthesis and in vitro antimicrobial activity of 6-substituted 2H-1,3,5-thiadiazine-2,4(3H)-diones

  摘要：

  A series of 6-substituted 2H-1,3,5-thiadiazine-2,4(3H)-diones (1a-m) was prepared by treatment of alkyl, aryl, and heterocyclic primary thioamides with phenoxycarbonyl isocyanate to give N-(phenoxycarbonyl)-N'-thioacylureas, which gave 1 upon heating in refluxing xylene solution or upon treatment with aqueous sodium carbonate solution followed by acidification. 1H NMR and infrared spectral evidence indicates that the 6-alkyl derivatives 1a,b,l,m exist predominately in the exocyclic alkylidene tautomeric form. The major product obtained from alkaline and acid hydrolysis of the 6-phenyl derivative 1c was found to be benzoic acid and benzoylurea, respectively. The majority of compounds 1a-m exhibited in vitro antifungal activity against Candida albicans and Trichophyton mentagrophytes. Several derivatives, 1b-d,h,j, displayed minimum inhibitory concentration values below 2 micrograms/mL against Trichophyton mentagrophytes. Four derivatives, 1c,e,g,h, inhibited the growth of Seratia marcesens, Staphylococcus aureus, and Staphylococcus epidermis in an in vitro sensitivity disk assay. 2-Furyl derivative 1h displayed antileukemic activity against P-388 lymphocytic leukemia.

  DOI：

  10.1021/jm00346a028
• 作为产物：
  描述：

  对氰基苯乙酮 在 劳森试剂 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 12.33h， 以70%的产率得到4-acetylbenzothioamide
  参考文献：
  名称：

  The BF₃×OEt₂-Assisted Conversion of Nitriles into Thioamides with Lawesson’s Reagent

  摘要：

  报道了一种利用Lawesson试剂进行腈的硫解反应的方法，并通过添加三氟化硼二乙醚复合物来促进反应。该方法为制备一级硫酰胺提供了简便途径。芳香族、苄基和脂肪族腈在高至定量的产率下被转化为相应的硫酰胺（即使在不利情况下，例如邻位取代的苄腈）。反应在1,2-二甲氧基乙烷-四氢呋喃或甲苯-二乙醚溶剂混合物中于20-50℃进行，并对多功能腈底物表现出显著的选择性，如氰甲基N-乙酰苯丙氨酸酯、苯甲酰丙二腈、4-氰基苯甲酰胺、4-乙酰基苯甲腈或戊-3-烯腈。

  DOI：

  10.1055/s-0028-1083253

文献信息

• Methods for minimizing thioamide impurities
  申请人：Wilk Kazimierz Bogdan

  公开号：US20050228179A1

  公开（公告）日：2005-10-13

  Methods for minimizing the formation of thioamide compounds using decoy agents during reactions, such as thionations of carbonyl compounds containing nitrite groups, are provided.

  使用诱饵剂来减少在反应过程中形成硫代酰胺化合物的方法，例如在含有亚硝基团的羰基化合物的硫代化反应中。
• NaHS·<i>n</i>H₂O-induced umpolung: the synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles
  作者：Xiao Geng、Xia Wu、Can Wang、Peng Zhao、You Zhou、Xuan Sun、Ling-Jiao Wang、Wen-Juan Guan、Yan-Dong Wu、An-Xin Wu

  DOI：10.1039/c8cc07599a

  日期：——

  An efficient method for constructing 2-acyl-3-aminoindoles from methyl ketones and 2-aminobenzonitriles is described, in which NaHS·nH2O is used as a novel umpolung reagent for the first time in organic synthesis. Mechanistic studies revealed that the key step involved an Eschenmoser sulfide contraction reaction.

  描述了一种由甲基酮和2-氨基苯甲腈构建2-酰基-3-氨基吲哚的有效方法，其中NaHS· n H 2 O首次在有机合成中用作新型的酚试剂。机理研究表明，关键步骤涉及Eschenmoser硫化物的收缩反应。
• A divergent and metal free synthesis of sulfoximine tethered imidazoles, imidazopyridines, imidazothiazoles, imidazobenzothiazines, thiazoles and selenazoles
  作者：S. R. K. Battula、V. P. Rama Kishore Putta、G. V. Subbareddy、I. E. Chakravarthy、V. Saravanan

  DOI：10.1039/c7ob00601b

  日期：——

  A divergent and metal free approach has been successfully developed for the synthesis of sulfoximine tethered heterocycles. A key α-bromoalkanone intermediate 3b has been reported for the first time. Various sulfoximine tethered imidazoles, imidazopyridines, thiozoloimidazoles, imidazobenzothiazines, thiazoles and selenazoles are made from this common sulfoximine building block.

  已成功开发出一种无金属扩散的方法，用于合成亚砜亚胺系链的杂环。首次报道了关键的α-溴烷酮中间体3b。各种磺胺亚胺系的咪唑，咪唑并吡啶，硫唑基咪唑，咪唑并苯并噻嗪，噻唑和亚硒唑是由这种常见的磺肟基结构单元制成的。
• A metal- and base-free domino protocol for the synthesis of 1,3-benzoselenazines, 1,3-benzothiazines and related scaffolds
  作者：V. P. Rama Kishore Putta、Raghuram Gujjarappa、Ujjawal Tyagi、Prasad P. Pujar、Chandi C. Malakar

  DOI：10.1039/c8ob03058h

  日期：——

  Efficient and operationally simple protocols have been demonstrated for the synthesis of the title compounds using easily available starting materials under mild conditions, giving a broad range of rarely reported molecules in excellent yields.

  通过使用易得的起始材料，在温和条件下演示了合成标题化合物的高效和操作简单的协议，产率优秀，得到了广泛的罕见分子。
• [EN] COMPOSITIONS AND METHODS TO TREAT NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR TRAITER DES MALADIES NEURODÉGÉNÉRATIVES
  申请人：GEN HOSPITAL CORP

  公开号：WO2014015047A1

  公开（公告）日：2014-01-23

  The specification provides compositions and methods to treat neurodegenerative diseases.

  该规范提供了治疗神经退行性疾病的组成成分和方法。