2,3,5-triphenyl-4-thiazolone | 18100-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,3,5-triphenyl-4-thiazolone
• 英文别名: 2,3,5-triphenyl-3H-thiazol-1-ium-4-olate；4-oxo-2,3,5-triphenyl-4,5-dihydro-thiazolium betaine；2,3,5-Triphenyl-1,3-thiazol-4-one
• CAS: 18100-80-6
• 化学式: C₂₁H₁₅NOS
• 分子量: 329.422
• InChiKey: QYCFZXBTDQEHBO-UHFFFAOYSA-N

物化性质

• 熔点：
  233-236 °C (decomp)(Solv: benzene (71-43-2))

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  21.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,5-triphenyl-4-thiazolone 在 盐酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 生成 苯甲酰甲酸甲酯
  参考文献：
  名称：

  Reaction of mesoionic thiazolones with m-chloroperbenzoic acid. Oxidative dipole extensions

  摘要：

  DOI：

  10.1021/jo01312a009
• 作为产物：
  描述：

  DL-N,2-Diphenyl-2-<(thiobenzoyl)thio>acetamid 在 乙酸酐 、 三乙胺 作用下， 反应 0.17h， 以67%的产率得到2,3,5-triphenyl-4-thiazolone
  参考文献：
  名称：

  Gotthardt, Hans; Pflaumbaum, Wolfgang, Chemische Berichte, 1987, vol. 120, p. 1017 - 1022

  摘要：

  DOI：

文献信息

• Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes
  作者：Sabrina Bernard、Davide Audisio、Margaux Riomet、Sarah Bregant、Antoine Sallustrau、Lucie Plougastel、Elodie Decuypere、Sandra Gabillet、Ramar Arun Kumar、Jijy Elyian、Minh Nguyet Trinh、Oleksandr Koniev、Alain Wagner、Sergii Kolodych、Frédéric Taran

  DOI：10.1002/anie.201708790

  日期：2017.12.4

  We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the

  我们报告发现了一种新的生物正交的点击释放反应，涉及到亚氨基sydnones和应变炔烃。这种转化导致在生理条件下亚氨基sydnones的连接和断裂产生两种产物。优化的亚氨基缩醛成功用于设计用于蛋白质修饰的创新性可裂解连接子，从而在药物释放和目标捕捞应用领域开辟了新领域。这种点击释放技术可在温和生物正交条件下为功能化的环辛炔交换蛋白质上的标签。
• Antitrichomonal activity of mesoionic thiazolo[3,2-a]pyridines
  作者：Keith A. M. Walker、Eric B. Sjogren、Thomas R. Matthews

  DOI：10.1021/jm00149a023

  日期：1985.11

  Screening of mesoionic compounds as potential electron acceptors by analogy with metronidazole led to the finding of in vitro antitrichomonal activity for anhydro-2-phenyl-3-hydroxythiazolo [3,2-a]pyridinium hydroxide (1). In a series of analogues, potent in vitro activity was found to be associated with amino substitution; however, such activity was dependent on specific structural features and not

  通过与甲硝唑类比筛选作为潜在电子受体的中离子化合物，发现了对脱水-2-苯基-3-羟基噻唑[3,2-a]吡啶鎓氢氧化物的体外抗滴虫活性（1）。在一系列类似物中，发现有效的体外活性与氨基取代有关。但是，这种活性取决于特定的结构特征，而不取决于还原潜力。活性最高的化合物仅显示出较差的体内活性。
• PHOTOOXIDATION OF SOME MESOIONIC AND RELATED SYSTEMS
  作者：Hiroshi Kato、Kazue Tani、Haruki Eurumisawa、Yoshiko Tamura

  DOI：10.1246/cl.1980.717

  日期：1980.6.5

  Photooxidation of several mesoionic compounds gave ring cleavage products, some of which were apparently formed via the endoperoxides of the mesoionic rings. Photooxidation of a Δ2-oxazolin-4-one and a Δ2-thiazolin-4-one gave the corresponding 4,4′-bisoxa- and bisthiazolinone in dichloromethane, whereas the former gave benzamide in dimethylformamide.

  几种介离子化合物的光氧化产生环裂解产物，其中一些显然是通过介离子环的内过氧化物形成的。Δ2-oxazolin-4-one 和 Δ2-thiazolin-4-one 的光氧化在二氯甲烷中产生相应的 4,4'-bisoxa- 和双噻唑啉酮，而前者在二甲基甲酰胺中产生苯甲酰胺。
• Heterocycles by Cycloaddition. IV. Cycloaddition Reactions of Mesoionic Compounds with a 7-Azabicyclo[2.2.1]heptadiene, and Double Fragmentation of the Adducts
  作者：Hiroshi Matsukubo、Hiroshi Kato

  DOI：10.1246/bcsj.49.3314

  日期：1976.11

  Cycloaddition of some five-membered mesoionic compounds with dimethyl 7-tosyl-7-azabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate occurs only across the unsubstituted double bond. Pyrolysis of the adducts resulted in a double fragmentation reaction to give two five-membered aromatic heterocycles. A dithiolone adduct gave the S-oxide, which was pyrolyzed to the corresponding thiopyran-2-one.

  一些五元介离子化合物与 7-tosyl-7-azabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 的环加成仅发生在未取代的双键上。加合物的热解导致双断裂反应，得到两个五元芳族杂环。二硫醇酮加合物生成 S-氧化物，将其热解为相应的噻喃-2-酮。
• Interception of photochemical intermediate of thiazole derivatives. Formation and isomeristion of iminoazetine and azetinone intermediates
  作者：Hiroshi Kato、Kozo Wakao、Akira Yamada、Masanobu Kojima

  DOI：10.1039/c39840001558

  日期：——

  Irradiation of 4-aminothiazolium salts (7) in the presence of tributylphosphine gave enaminonitriles 9) and benzoylacetonotrile (8) by isomerisation and hydration of the iminoazetine intermediates (11), while a similar irradiation of the mesoionic triphenylthiazolium-4-oate (1) gave the quinolinol (5) by isomerisation of the azetione intermediate (3).

  4- aminothiazolium盐（照射7在三丁基膦的存在下），得到enaminonitriles 9）和benzoylacetonotrile（8由iminoazetine中间体（异构化和水合）11），而中离子triphenylthiazolium-4 -酸酯的类似照射（1）得到羟基喹啉（5由azetione中间体（异构化）3）。