2,2,2-trifluoro-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide | 22926-49-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2,2-trifluoro-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide
• 英文别名: 5-methyl-2-trifluoroacetylamino-1,3,4-thiadiazole；2,2,2-trifluoro-N-(5-methyl-[1,3,4]thiadiazol-2-yl)-acetamide；5-Methyl-2-trifluoracetamino-1,3,4-thiadiazol
• CAS: 22926-49-4
• 化学式: C₅H₄F₃N₃OS
• 分子量: 211.167
• InChiKey: FTSRBUYSTNETDX-UHFFFAOYSA-N

物化性质

• 密度：
  1.610±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide 、 N-(三苯基甲基)-5-(4'-溴甲基联苯-2-基)四氮唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Quantitative structure-activity relationships of benzoyliminothiadiazoline derivatives as angiotensin II receptor antagonists

  摘要：

  Syntheses and biological activities of benzoyliminothiadiazoline derivatives which have potential affinities for angiotensin II receptor are described. The contributions of substituent (R(1)) on the benzene ring in benzoyl moiety and 5-position substituent (R(2)) on the 1,3,4-thiadiazoline ring were quantitatively investigated. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00026-7
• 作为产物：
  描述：

  2-氨基-5-甲基-1,3,4-噻二唑 、 三氟乙酸酐 以 甲苯 为溶剂， 以80%的产率得到2,2,2-trifluoro-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of New 1.BETA.-Methylcarbapenems Having the Potential for Intramolecular Nonbonded S...O Interactions.

  摘要：

  高效合成了用于1β-甲基碳青霉烯抗生素的悬挂基团的巯基乙酰亚胺噻二唑啉衍生物（19, 20）。衍生物20的乙酰衍生物（18）提交进行了X射线分析，并在晶体结构中识别出了显著的非键合S…O近接接触。通过利用19和20合成了新的1β-甲基碳青霉烯（5, 6），在体外表现出相当的抗菌活性。

  DOI：

  10.1248/cpb.49.1660

文献信息

• Synthesis and Antibacterial Activity of New 1.BETA.-Methylcarbapenems Having the Potential for Intramolecular Nonbonded S...O Interactions.
  作者：Yoshimitsu NAGAO、Hitoshi IIMORI、Ki Hong NAM、Shigeki SANO、Motoo SHIRO

  DOI：10.1248/cpb.49.1660

  日期：——

  Mercaptoacetyliminothiadiazoline derivatives (19, 20) useful for the pendant moiety of 1β-methylcarbapenem antibiotics were efficiently synthesized. Acetyl derivative (18) of 20 was submitted to X-ray analysis, and a significant nonbonded S…O close contact was recognized in the crystallographic structure. New 1β-methylcarbapenems (5, 6) were synthesized by exploiting 19 and 20, and exhibited considerable antibacterial activities in vitro.

  高效合成了用于1β-甲基碳青霉烯抗生素的悬挂基团的巯基乙酰亚胺噻二唑啉衍生物（19, 20）。衍生物20的乙酰衍生物（18）提交进行了X射线分析，并在晶体结构中识别出了显著的非键合S…O近接接触。通过利用19和20合成了新的1β-甲基碳青霉烯（5, 6），在体外表现出相当的抗菌活性。
• Sulfamic Acid–Mediated, Efficient, One-Pot Synthesis of Novel 5-Substituted 1,3,4-Thiadiazol-2-ylcarbamoyl Aliphatic Amide Acid Derivatives and Facile Synthesis of Cyclic Amides
  作者：R. B. Toche、R. A. Janrao、S. A. Gangurde、P. S. Nikam

  DOI：10.1080/00397911.2012.719256

  日期：2013.9.17

  Abstract Convenient and efficient one-pot syntheses of 5-substituted-1,3,4-thiadiazol-2-ylcarbamoyl aliphatic amide acid derivatives were described and developed using sulfamic acid catalyst. Thiosemicarbazide and substituted triethylorthoester and cyclic/alicyclic anhydride were efficiently condensed using sulfamic acid to furnish 5-disubstituted-1,3,4-thiadiazol-2-ylcarbamoyl aliphatic acid and amide

  摘要 描述并开发了使用氨基磺酸催化剂方便、高效地一锅法合成 5-取代-1,3,4-噻二唑-2-基氨基甲酰基脂肪酰胺酸衍生物的方法。使用氨基磺酸有效地将氨基硫脲和取代的三乙基原酸酯和环/脂环酸酐缩合，得到 5-二取代的 1,3,4-噻二唑-2-基氨基甲酰基脂肪酸和酰胺衍生物，收率相当到良好，仅环化成新的环状酰胺衍生物。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Gagiu; Daicoviciu; Binder, Pharmazie, 1969, vol. 24, # 2, p. 98 - 99
  作者：Gagiu、Daicoviciu、Binder、Gyoerfi

  DOI：——

  日期：——
• Quantitative structure-activity relationships of benzoyliminothiadiazoline derivatives as angiotensin II receptor antagonists
  作者：Terukage Hirata、Satoru Goto、Koichi Tamura、Masayasu Okuhira、Yoshimitsu Nagao

  DOI：10.1016/s0960-894x(97)00026-7

  日期：1997.2

  Syntheses and biological activities of benzoyliminothiadiazoline derivatives which have potential affinities for angiotensin II receptor are described. The contributions of substituent (R(1)) on the benzene ring in benzoyl moiety and 5-position substituent (R(2)) on the 1,3,4-thiadiazoline ring were quantitatively investigated. (C) 1997, Elsevier Science Ltd.
• Innovative Strategy toward Mutant CFTR Rescue in Cystic Fibrosis: Design and Synthesis of Thiadiazole Inhibitors of the E3 Ligase RNF5
  作者：Irene Brusa、Elvira Sondo、Emanuela Pesce、Valeria Tomati、Dario Gioia、Federico Falchi、Beatrice Balboni、Jose Antonio Ortega Martínez、Marina Veronesi、Elisa Romeo、Natasha Margaroli、Maurizio Recanatini、Stefania Girotto、Nicoletta Pedemonte、Marinella Roberti、Andrea Cavalli

  DOI：10.1021/acs.jmedchem.3c00608

  日期：2023.7.27