2-benzylideneamino-4-phenylthiazole | 13148-56-6

• 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-benzylideneamino-4-phenylthiazole
• 英文别名: N-(4-phenyl-1,3-thiazol-2-yl)phenylmethanimine；2-benzylideneamino-4-phenyl-5-bromo-1,3-thiazole；2-benzylideneamino-4-phenyl-1,3-thiazole；N-[phenylmethylidene]-N-(4-phenyl-1,3-thiazol-2-yl)amine；benzylidene-(4-phenyl-thiazol-2-yl)-amine；Benzyliden-(4-phenyl-thiazol-2-yl)-amin；2-(Benzyliden-amino)-4-phenyl-thiazol；4-Phenyl-benzyliden-2-aminothiazol；4-Phenyl-N-(phenylmethylene)-2-thiazolamine；1-phenyl-N-(4-phenyl-1,3-thiazol-2-yl)methanimine
• CAS: 13148-56-6
• 化学式: C₁₆H₁₂N₂S
• 分子量: 264.351
• InChiKey: WNQLXXHCCUAUIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzylideneamino-4-phenylthiazole 在 硫酸 作用下， 反应 0.72h， 生成 (6R,7S)-6-Amino-3,7-diphenyl-6,7-dihydro-thiazolo[3,2-a]pyrimidin-5-one
  参考文献：
  名称：

  微波辐照下噻唑上嘧啶环无溶剂的一锅法反应

  摘要：

  甘氨酸，乙酸酐和噻唑席夫碱（2a – f）的一锅反应非对映选择性，迅速使噻唑核上的嘧啶环脱环，得到6,7-dihydro-5 H -thiazolo [3,2- a ]嘧啶-在微波辐射和无溶剂条件下为5-1（4a – f）。

  DOI：

  10.1016/s0040-4020(03)00854-8
• 作为产物：
  描述：

  2-氨基-4-苯基噻唑 、 苯甲醛 以 乙醇 为溶剂， 以71%的产率得到2-benzylideneamino-4-phenylthiazole
  参考文献：
  名称：

  超声辐射和耦合辐射下3,7-二芳基-6,7-二氢-5H-6取代的噻唑并[3,2-a]嘧啶-5-酮的杀虫性评估和[4 + 2] Aza-Diels-Alder合成PTC

  摘要：

  一系列3,7-二芳基-6,7-二氢-5 H -6-取代的噻唑并[3,2-a]嘧啶-5-酮（3a，3b，3c，3d，3e，3f，3g，3h，3i，3j）是通过2-芳基亚氨基-4-芳基噻唑（2a–j）与原位的[4 + 2]环加成反应合成的在PTC条件下生成的单取代乙烯酮，再加上超声处理，收率良好。所有合成的化合物均根据其光谱（IR，PMR和质量）和分析数据进行表征。还筛选了合成的化合物对棉铃虫的杀虫活性，其中一些化合物显示出有希望的活性。

  DOI：

  10.1002/jhet.776

文献信息

• [4+2] Diels–Alder Cycloaddition Reaction of 2-benylidineamino-4-phenyl-1,3-thiazoles with Sulfene and their Antifungal Activities
  作者：Susanta Kr. Borthakur、Paran Boruah、Birendra N. Goswami

  DOI：10.3184/030823407x191877

  日期：2007.2

  2-Benzylidineamino-4-phenyl-1,3-thiazole undergoes [4+2] Diels–Alder cycloaddition reaction with sulfene resulting in good yield of a mixture of isomeric 2,6-diphenyl-2H,4H-[1,3]thiazolo[3,2-c][1,3,5]thiadiazine 3,3-dioxides and 3, 7-diphenyl[1,3]thiazolo[3,2-b] [1,2,4]thiadiazine 5,5-dioxides derivatives are reported.

  2-Benzylidineamino-4-phenyl-1,3-thiazole 与亚砜发生 [4+2] Diels-Alder 环加成反应，得到良好的异构体 2,6-diphenyl-2H,4H-[1,3] 混合物噻唑并[3,2-c][1,3,5]噻二嗪3,3-二氧化物和3,7-二苯基[1,3]噻唑并[3,2-b][1,2,4]噻二嗪5，报道了 5-二氧化物衍生物。
• Design of New Cognition Enhancers:  From Computer Prediction to Synthesis and Biological Evaluation
  作者：Athina A. Geronikaki、John C. Dearden、Dmitrii Filimonov、Irina Galaeva、Taissia L. Garibova、Tatiana Gloriozova、Valentina Krajneva、Alexey Lagunin、Fliur Z. Macaev、Guenadij Molodavkin、Vladimir V. Poroikov、Serghei I. Pogrebnoi、Felix Shepeli、Tatiana A. Voronina、Maria Tsitlakidou、Liudmila Vlad

  DOI：10.1021/jm031086k

  日期：2004.5.1

  To discover new cognition enhancers, a set of virtually designed synthesizable compounds from different chemical series was investigated using two computer-aided approaches. One of the approaches is prediction of biological activity spectra for substances (PASS) and the second is prediction of toxicity, mutagenicity, and carcinogenicity (DEREK). To increase the probability of finding new chemical entities, we investigated a heterogeneous set of highly diverse chemicals including different types of heterocycles: five-membered (thiophenes, thiazoles, imidazoles, oxazoles, pyrroles), six-membered (pyridines, pyrimidines), seven-membered (diazepines, triazepines), fused five+six-membered heterocycles (indoles, benzothiazoles, purines, indolizines, neutral, mesoionic, and cationic azolopyridines). A database including 5494 structures of compounds was created. On the basis of the PASS and DEREK prediction results, eight compounds with the highest probability of cognition-enhancing effect were selected. The cognition-enhancing activity testing showed that all of the selected compounds had a pronounced antiamnesic effect and were found to reduce significantly scopolamine-induced amnesia of passive avoidance reflex (PAR). The action of compounds at doses of 1 and 10 mg/kg caused a statistically significant increase in latent time of reflex and in the number of animals, which did not enter the dark chamber when testing the PAR. Therefore, on the basis of computer prediction, new cognition-enhancing agents were discovered within the chemical series, in which this activity was not known previously.
• Fromm; Kapeller-Adler, Justus Liebigs Annalen der Chemie, 1928, vol. 467, p. 254
  作者：Fromm、Kapeller-Adler

  DOI：——

  日期：——
• Praharaj; Dash; Mohapatra, Journal of the Indian Chemical Society, 1981, vol. 58, # 12, p. 1184 - 1186
  作者：Praharaj、Dash、Mohapatra

  DOI：——

  日期：——
• Synthesis and Complexing Properties of 4-Arylthiazolyl-substituted Schiff Bases
  作者：S. E. Sadigova、A. M. Magerramov、M. A. Allakhverdiev、R. A. Alieva、F. M. Chyragov、T. M. Vekilova

  DOI：10.1023/b:rugc.0000025156.16373.17

  日期：2003.12

  Reactions of 2-amino-4-arylthiazoles with aromatic aldehydes afforded the corresponding Schiff bases. Complex formation of the latter with nickel, zinc, cobalt, manganese, and copper salts was studied.