N-1,3,4-噻二唑-2-基乙酰胺 | 5393-55-5

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-1,3,4-噻二唑-2-基乙酰胺
• 中文别名: 乙酰唑胺杂质
• 英文名称: 2-acetylamino-1,3,4-thiadiazole
• 英文别名: 2-acetamido-[1,3,4]thiadiazole；2-acetamido-1,3,4-thiadiazole；5-acetamido-1,3,4-thiadiazole；N-[1,3,4]thiadiazol-2-yl-acetamide；N-[1,3,4]Thiadiazol-2-yl-acetamid；N-Acetyl-2-amino-1,3,4-thiadiazol；n-(1,3,4-Thiadiazol-2-yl)acetamide
• CAS: 5393-55-5
• 化学式: C₄H₅N₃OS
• mdl: MFCD00500775
• 分子量: 143.169
• InChiKey: YOGFGFKRNRQDMF-UHFFFAOYSA-N

物化性质

• 熔点：
  350 °C
• 密度：
  1.454±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶，超声处理），甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  N-1,3,4-噻二唑-2-基乙酰胺 在 盐酸 作用下， 生成 2-氨基-1,3,4-噻二唑
  参考文献：
  名称：

  Kanaoka, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 1149,1151

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-1,3,4-噻二唑 生成 N-1,3,4-噻二唑-2-基乙酰胺
  参考文献：
  名称：

  Pentimalli,L. et al., Gazzetta Chimica Italiana, 1975, vol. 105, p. 777 - 787

  摘要：

  DOI：

文献信息

• 1H,13C,15N and19F NMR study of acetylation products of heterocyclic thiosemicarbazones
  作者：Lyudmila I. Larina、Valentina N. Elokhina、Tatyana I. Yaroshenko、Anatolii S. Nakhmanovich、Gennadii V. Dolgushin

  DOI：10.1002/mrc.2006

  日期：2007.8

  eryl)‐1,3,4‐thiadiazoles, and some of their salts were prepared and studied by multinuclear 1H, 13C, 15N, 19F and 2D NMR spectroscopy. The acetylation of thiosemicarbazones is accompanied by ring closure to form the corresponding 1,3,4‐thiadiazolines and 1,3,4‐thiadiazoles. 15N NMR spectroscopy is a unique method for the identification of thiadiazole pyridinium salts. Copyright © 2007 John Wiley &

  制备了新型 2-乙酰氨基-4-乙酰基-5-芳基(杂基)-1,3,4-噻二唑啉、2-乙酰氨基-5-芳基(杂基)-1,3,4-噻二唑及其部分盐并通过多核 1H、13C、15N、19F 和 2D 核磁共振波谱研究。缩氨基硫脲的乙酰化伴随着闭环形成相应的 1,3,4-噻二唑啉和 1,3,4-噻二唑。15N NMR 光谱是鉴定噻二唑吡啶鎓盐的独特方法。版权所有 © 2007 John Wiley & Sons, Ltd.
• Synthesis, Oxidation and Dehydro- genation of Cyclic N,O- and N,S-Acetals. Part 1. Transformation of N,S-Acetals: 3-Acyl-1,3,4-thiadiazolines
  作者：László Somogyi

  DOI：10.3987/com-04-10137

  日期：——

  Aldehyde and ketone thiosemicarbazones are synthesized and cyclized into 3-acyl-1,3,4-thiadiazolines under acylating conditions. Reactions of the 2-monosubstituted heterocycles with oxidizing and dehydrogenating agents (KMnO 4 or for the first time with CAN, DDQ, IBDA) lead to the formation of thiadiazoles. CAN oxidation of 2,2-disubstituted 3-acyl-1,3,4-thiadiazolines regenerates the parent ketones

  醛和酮缩氨基硫脲在酰化条件下合成并环化成 3-酰基-1,3,4-噻二唑啉。2-单取代杂环与氧化剂和脱氢剂（KMnO 4 或首次与 CAN、DDQ、IBDA）反应导致形成噻二唑。2,2-二取代 3-acyl-1,3,4-thiadiazolines 的 CAN 氧化可有效地再生母体酮。
• The synthesis and reactivity of some 2-amino-5-bromo-],1,3,4-thiadiazoles and the corresponding Δ²-1,3,4-thiadiazolines
  作者：Giuseppe Werber、Francesco Buccheri、Manlio Gentile

  DOI：10.1002/jhet.5570140521

  日期：1977.8.4

  The synthesis of some 2-amino-5-bromo-1,3,4-thiadiazoles is reported; these substrates are found to behave as ambidenl nucleophiles in alkylation, aeylation and nitrosation reactions, giving thiadiazoliens along with thiadiazole derivatives. This finding suggests amine-imine tautomerism between these compounds and the corresponding Δ2-1,3,4-thiadiazolines.

  据报道一些2-氨基-5-溴-1,3,4-噻二唑的合成。发现这些底物在烷基化，缩醛反应和亚硝化反应中表现出环糊状亲核试剂的作用，生成噻二唑和噻二唑衍生物。这一发现表明这些化合物和相应Δ之间胺-亚胺互变异构2 -1,3,4-噻二唑类。
• Synthesis and Crystal Structure of 2-Aminoacetyl-1,3,4-thiadiazole
  作者：Sh. A. Kadirova、G. A. Nuralieva、M. A. Alieva、S. A. Talipov、Z. G. Tilyakov、N. A. Parpiev

  DOI：10.1007/s11176-006-0022-2

  日期：2005.12

  2-Aminoacetyl-1,3,4-thiadiazole was synthesized, and its structure was studied. In crystal, the thiadiazole molecules form hydrogen-bonded endless one-dimensional chains related by the glide reflection plane.

  合成了 2-氨基乙酰基-1,3,4-噻二唑，并对其结构进行了研究。在晶体中，噻二唑分子通过滑行反射面形成氢键连接的无尽一维链。
• GIAO/DFT ¹³C NMR Chemical Shifts of 1,3,4-Thiadiazoles
  作者：Hossein Loghmani-Khouzani、Teresa Rauckyte、Borys Ośmiałowski、Ryszard Gawinecki、Erkki Kolehmainen

  DOI：10.1080/10426500701407755

  日期：2007.7.19

  H-1, C-13 and N-15 NMR spectra of 2-acetylamino-1,3,4-thiadiazole and its 5-substituted derivatives have been measured and assigned based on reference data, as well as homo- and heteronuclear 2 D NMR experiments. In addition, the GIAO/DFT approach at the B3LYP level of theory using the 6-311G basis set was used to calculate the C-13 NMR chemical shifts. Although this method gives reliable results for 2-arylhydrazones of 1,3-diphenylpropanetrione, 2-phenacylpyridines, (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines, 4-fluoroanilines, (1Z,3Z)-1,4-di(pyridin-2-yl)buta-1,3-dienediols and their tautomeric forms, the calculated chemical shifts for the 1,3,4-thiadiazoles studied are less satisfactory. Presence of the sulfur atom(s) seems to be responsible for such behavior.

表征谱图