1-(5-苯胺-1,2,4-噻二唑-3-基)乙酮 | 64822-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(5-苯胺-1,2,4-噻二唑-3-基)乙酮
• 英文名称: 1-(5-anilino-[1,2,4]thiadiazol-3-yl)-propan-2-one
• 英文别名: 3-Acetonyl-5-anilino-1,2,4-thiadiazol；1-[5-(Phenylamino)-1,2,4-thiadiazol-3-yl]propan-2-one；1-(5-anilino-1,2,4-thiadiazol-3-yl)propan-2-one
• CAS: 64822-00-0
• 化学式: C₁₁H₁₁N₃OS
• mdl: MFCD00084856
• 分子量: 233.294
• InChiKey: XLJGKAGJWBNCSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C(Solv: benzene (71-43-2))
• 沸点：
  394.3±44.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1-(5-苯胺-1,2,4-噻二唑-3-基)乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-[5-(phenylamino)-1,2,4-thiadiazol-3-yl]propan-2-ol
  参考文献：
  名称：

  Novel 1,2,4-Thiadiazole Derivatives as Potent Neuroprotectors: Approach to Creation of Bioavailable Drugs

  摘要：

  Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and identified. Their ability to inhibit the glutamate stimulated Ca uptake was measured. Permeation experiments on the phospholipid membranes were conducted, and the apparent permeability coefficients were obtained. The partition coefficients in n-octanol/buffer (pH 7.4) and n-hexane/buffer (pH 7.4) immiscible phases (as model systems for characterizing gastrointestinal tract membranes and BBB) were determined. A classification of the studied compounds from the standpoint of "permeability-activity" properties was proposed.

  DOI：

  10.1021/mp300011r
• 作为产物：
  描述：

  1-(5-甲基-3-异恶唑基)-3-苯基硫脲 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 1-(5-苯胺-1,2,4-噻二唑-3-基)乙酮
  参考文献：
  名称：

  Vivona, Nicolo; Cusmano, Giuseppe; Macaluso, Gabriella, Journal of the Chemical Society. Perkin transactions I, 1977, # 14, p. 1616 - 1619

  摘要：

  DOI：

文献信息

• 1-(5-(<i>R</i>-Amino)-1,2,4-thiadiazol-3-yl)propan-2-ones: Convenient Ketomethylenic Reagents for the Gewald and Dimroth Reactions
  作者：Nazariy T. Pokhodylo、Olga Ya. Shyyka

  DOI：10.1002/jhet.1719

  日期：2014.9

  1‐(5‐(R‐Amino)‐1,2,4‐thiadiazol‐3‐yl)propan‐2‐ones were used as activated ketomethylenic compounds for the Gewald and Dimroth reactions. It was found out that they exhibited high reactivity in such anion reactions for the construction of the 1,2,3‐triazole and thiophene frameworks. The target 1,2,3‐triazoles and thiophenes were obtained in high yields in minimum time.

  1-（5-（R-氨基）-1,2,4-噻二唑-3-基）丙-2-酮被用作Gewald和Dimroth反应的活化酮亚甲基化合物。结果发现，它们在构建1,2,3-三唑和噻吩骨架的阴离子反应中显示出很高的反应性。在最短时间内以高收率获得了目标1,2,3-三唑和噻吩。
• Novel 1,2,4-thiadiazoles with an NO-producing fragment
  作者：I. V. Serkov、A. N. Proshin、L. N. Petrova、S. O. Bachurin

  DOI：10.1134/s0012500810120013

  日期：2010.12
• Novel binary compounds derived from 1,2,4-thiadiazole
  作者：A. N. Proshin、I. V. Serkov、S. O. Bachurin

  DOI：10.1134/s0012500812090017

  日期：2012.9
• Vivona, Nicolo; Cusmano, Giuseppe; Macaluso, Gabriella, Journal of the Chemical Society. Perkin transactions I, 1977, # 14, p. 1616 - 1619
  作者：Vivona, Nicolo、Cusmano, Giuseppe、Macaluso, Gabriella

  DOI：——

  日期：——
• Novel 1,2,4-Thiadiazole Derivatives as Potent Neuroprotectors: Approach to Creation of Bioavailable Drugs
  作者：German L. Perlovich、Alexey N. Proshin、Tatyana V. Volkova、Ludmila N. Petrova、Sergey O. Bachurin

  DOI：10.1021/mp300011r

  日期：2012.8.6

  Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and identified. Their ability to inhibit the glutamate stimulated Ca uptake was measured. Permeation experiments on the phospholipid membranes were conducted, and the apparent permeability coefficients were obtained. The partition coefficients in n-octanol/buffer (pH 7.4) and n-hexane/buffer (pH 7.4) immiscible phases (as model systems for characterizing gastrointestinal tract membranes and BBB) were determined. A classification of the studied compounds from the standpoint of "permeability-activity" properties was proposed.