N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide | 28898-88-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide
• 英文别名: 2-(Acetamido)-5-phenyl-1,3,4-thiadiazole
• CAS: 28898-88-6
• 化学式: C₁₀H₉N₃OS
• mdl: MFCD00453644
• 分子量: 219.267
• InChiKey: MOHXQYYZAKQQCP-UHFFFAOYSA-N

物化性质

• 熔点：
  282 °C
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide 在 一水合肼 作用下， 生成 2-氨基-5-苯基-1,3,4-噻二唑
  参考文献：
  名称：

  Synthesis of 4-acyl-2-(acylamino)-.DELTA.2-1,3,4-thiadiazolines and 4-acyl-2-amino-.DELTA.2-1,3,4-thiadiazolines by acylation of thiosemicarbazones

  摘要：

  DOI：

  10.1021/jo01296a025
• 作为产物：
  描述：

  原苯甲酸三乙酯 以 甲醇 为溶剂， 反应 2.42h， 生成 N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide
  参考文献：
  名称：

  氨基磺酸介导的新型 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高效一锅法合成和环酰胺的简便合成

  摘要：

  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

  DOI：

  10.1080/00397911.2012.719256

文献信息

• Synthesis of cephalosporins with substituted thiadiazoles directly attached to the C3-position. I. Synthesis of 3-(5-substituted-1,3,4-thiadiazol-2-yl)ceph-3-em derivatives.
  作者：TOHRU SUGAWARA、HIROTOMO MASUYA、TAISUKE MATSUO、TAKUICHI MIKI

  DOI：10.1248/cpb.28.2116

  日期：——

  3-(5-Substituted-1, 3, 4-thiadiazol-2-yl) ceph-3-em derivatives were prepared by oxidative ring closure with 2, 3-dichloro-5, 6-dicyanobenzoquinone directly or after acetylation of 3-thiocarbonylhydrazones, which were obtained from the reaction of 3-formylceph-3-ems and thiocarbonylhydrazines. The antibacterial activity of 7-thienylacetamido-3-(5-substituted-1, 3, 4-thiadiazol-2-yl) ceph-3-em derivatives (4) against gram-positive organisms was similar to that of cephalothin (CET), while the activity against gram-negative organisms was superior to that of CET. A similar oxidative ring closure reaction with other thiocarbonylhydrazones is also discussed.

  通过氧化环合反应，以2,3-二氯-5,6-二氰基苯醌直接或先经乙酰化3-硫羰基腙制得了3-(5-取代-1,3,4-噻二唑-2-基)头孢-3-烯衍生物。这些3-硫羰基腙是从3-醛基头孢-3-烯和硫羰基酰肼反应得到的。7-噻吩基乙酰胺基-3-(5-取代-1,3,4-噻二唑-2-基)头孢-3-烯衍生物(4)对革兰氏阳性菌的抗菌活性与头孢噻吩(CET)相似，而对革兰氏阴性菌的活性则优于CET。还讨论了与其他硫羰基腙的类似氧化环合反应。
• The synthesis and cyclisation of thioacylated diaminoguanidines
  作者：Frederick Kurzer、Jane L. Secker

  DOI：10.1016/s0040-4020(01)92462-7

  日期：1981.1

  1-amino-2-thioaroylamidoguanidines which are isolable as their stable hydrazones. They are unaffected by alkalis, but are cyclised by mineral acids, with loss of ammonia, to hydrazones of 2-aryl-5-hydrazino-1,3,4-thiadiazoles, or with elimination of hydrazine, to the appropriate 2-amino-5-aryl-1,3,4-thiadiazoles. The action of acetic anhydride effects the same ring-closures, yielding the corresponding acetylated

  1,2-二氨基胍的硫代苯甲酰化反应产生1-氨基-2-硫代芳基酰胺基胍，它们可作为稳定的而分离。它们不受碱的影响，但被无机酸环化，失去氨，生成2-芳基-5-肼基-1,3,4-噻二唑的azo，或消除肼，生成合适的2-氨基- 5-芳基-1,3,4-噻二唑。乙酸酐的作用影响相同的闭环，产生相应的乙酰化产物。1,2-二氨基-3-苯基胍经历了一系列类似的反应。
• Stereoselective S-oxidation of 5-substituted 4-acetyl-Δ²-1,3,4-thia-diazolines: X-ray crystal structure of 4-acetyl-2-acetylamino-5-methy-5-phenyl-Δ²-1,3,4-thiadiazoline 1-oxide
  作者：Seiju Kubota、Kouhei Toyooka、Naoya Yamamoto、Masayuki Shibuya、Masaru Kido

  DOI：10.1039/c39820000901

  日期：——

  N.m.r. spectroscopy and X-ray crystallography show that oxidation of 5-substituted 4-acetyl-2-acetylamino-Δ2-1,3,4-thiadiazolines with m-chloroperbenzoic acid gives the corresponding Δ2-1,3,4-thiadiazoline 1-oxides; the novel reactions of the product (2a) are also described.

  N.m.r. 光谱和 X 射线晶体学显示，用间氯过苯甲酸氧化 5-取代的 4-乙酰基-2-乙酰氨基δ2-1,3,4-噻二唑啉，可得到相应的δ2-1,3,4-噻二唑啉 1-氧化物；还描述了产物 (2a) 的新型反应。
• Heterocyclic Compounds Which Modulate The CB2 Receptor
  申请人：Bartolozzi Alessandra

  公开号：US20110312944A1

  公开（公告）日：2011-12-22

  Compounds which modulate the CB2 receptor are disclosed. Compounds according to the invention bind to and are agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.

  本发明揭示了调节CB2受体的化合物。根据本发明，这些化合物与CB2受体结合并作为激动剂，用于治疗炎症。那些作为激动剂的化合物还可用于治疗疼痛。
• Pyrrolidine Compounds Which Modulate The CB2 Receptor
  申请人：Berry Angela

  公开号：US20120142677A1

  公开（公告）日：2012-06-07

  Compounds which modulate the CB2 receptor are disclosed. Compounds according to the invention bind to and are agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain. (I)

  本发明揭示了调节CB2受体的化合物。本发明的化合物结合并激动CB2受体，并且可用于治疗炎症。那些是激动剂的化合物还可用于治疗疼痛。 (I)