4-(4-nitrophenyl)-N-phenyl-1,3-thiazol-2-amine | 102183-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-nitrophenyl)-N-phenyl-1,3-thiazol-2-amine
• 英文别名: 4-(4-nitrophenyl)-N-phenylthiazol-2-amine；4-(4-nitrophenyl)-2-phenylaminothiazole；[4-(4-nitro-phenyl)-thiazol-2-yl]-phenyl-amine；2-Phenylamino-4-<4-nitro-phenyl>-thiazol
• CAS: 102183-91-5
• 化学式: C₁₅H₁₁N₃O₂S
• mdl: MFCD00488210
• 分子量: 297.337
• InChiKey: XOHRNJAWXPLJHA-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C
• 沸点：
  496.3±37.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 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：
  99
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-nitrophenyl)-N-phenyl-1,3-thiazol-2-amine 、 三氟乙酸酐 以 甲苯 为溶剂， 反应 24.0h， 生成 4-(4-nitrophenyl)-2-(N-phenyl)trifluoroacetamidothiazole
  参考文献：
  名称：

  Bramley, (Miss) Susan E.; Dupplin, Viscount; Goberdhan, Dhanesh G. C., Journal of the Chemical Society. Perkin transactions I, 1987, p. 639 - 644

  摘要：

  DOI：
• 作为产物：
  描述：

  2-imino-4-(4-nitrophenyl)-3-phenyl-2,3-dihydrothiazole 在 盐酸 作用下， 反应 37.0h， 生成 4-(4-nitrophenyl)-N-phenyl-1,3-thiazol-2-amine
  参考文献：
  名称：

  Murav'eva,K.M.; Shchukina,M.N., Journal of general chemistry of the USSR, 1960, vol. 30, p. 2320 - 2323

  摘要：

  DOI：

文献信息

• Visible light triggered, catalyst free approach for the synthesis of thiazoles and imidazo[2,1-b]thiazoles in EtOH : H₂O green medium
  作者：Anu Mishra、Madhulika Srivastava、Pratibha Rai、Snehlata Yadav、Bhartendu Pati Tripathi、Jaya Singh、Jagdamba Singh

  DOI：10.1039/c6ra05385h

  日期：——

  The development of a visible light promoted, mild and greener approach for the synthesis of highly functionalized thiazoles and imidazo[2, 1-b]thiazoles under photochemical activation in EtOH:H2O green medium is demonstrated....

  证明了在EtOH：H2O绿色介质中在光化学活化下合成可见光促进，温和且绿色的方法的发展，该方法用于合成高度官能化的噻唑和咪唑并[2，1-b]噻唑。
• Effect of Substituents on the Regioselectivity of the Reaction of α-Tosyloxyketones with Thioureas in Acidic Medium: Access to 2-Aminothiazoles and 2-Imino-2,3-dihydrothiazoles
  作者：Ranjana Aggarwal、Rajiv Kumar、Dionisia Sanz、Rosa M. Claramunt

  DOI：10.1002/jhet.1676

  日期：2014.5

  Regioselective condensation of α‐tosyloxyacetophenones 1 and N‐substituted thioureas 2 in acidic medium to give regioisomers 2‐aminothiazoles I and 2‐imino‐2,3‐dihydrothiazoles II is largely influenced by the substituents present on 1 and 2. A mechanism, supported by DFT calculations has been proposed to explain the observed regioselectively.

  α-甲苯磺酰氧基苯乙酮1和N-取代的硫脲2在酸性介质中的区域选择性缩合反应产生区域异构体2-氨基噻唑I和2-亚氨基-2,3-二氢噻唑II在很大程度上受到1和2上存在的取代基的影响。已经提出了一种由DFT计算支持的机制来选择性地解释所观察到的区域。
• Green approach: an efficient synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles in aqueous medium under ultrasonic irradiation
  作者：Gondru Ramesh、Banothu Janardhan、Bavantula Rajitha

  DOI：10.1007/s11164-014-1879-z

  日期：2015.11

  An efficient and rapid procedure for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles has been described by the reaction of α-bromoketones with thiourea, phenylthiourea and selenourea at ambient temperature in aqueous medium under ultrasonic irradiation. Analytically pure products were formed within 10–60 s in excellent yields. The advantageous features of this non-conventional methodology

  已经描述了通过α-溴代酮与硫脲，苯硫脲和硒脲在水性介质中在超声辐射下于环境温度下的反应，描述了合成2,4-二取代-1,3-噻唑和硒代唑的有效且快速的方法。在10–60 s内即可形成分析纯产品，且产率极高。与常规方法相比，这种非常规方法的优势在于操作简单，易于处理，提高产量，减少时间，反应条件温和且不产生副产物。
• Sodium fluoride as an efficient catalyst for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles at ambient temperature
  作者：Janardhan Banothu、Krishnaiah Vaarla、Rajitha Bavantula、Peter A. Crooks

  DOI：10.1016/j.cclet.2013.10.001

  日期：2014.1

  Abstract Sodium fluoride was found to be a simple, mild and efficient catalyst for the synthesis of 2,4-disubstituted 1,3-thiazoles and selenazoles utilizing phenacyl bromides/3-(2-bromoacetyl)-2 H -chromen-2-one and thiourea/phenylthiourea/selenourea in aqueous methanol at ambient temperature. Analytically pure products are formed within 1–3 min in excellent yields.

  摘要发现氟化钠是一种简单，温和而有效的催化剂，用于利用苯甲酰溴/ 3-（2-溴乙酰基）-2H-铬-2--2-酮合成2,4-二取代的1,3-噻唑和亚硒唑在室温下，在甲醇水溶液中加入硫脲/苯硫脲/硒脲。在1到3分钟内即可形成具有解析力的纯产品，且产率极高。
• A library of novel allosteric inhibitors against fructose 1,6-bisphosphatase
  作者：Sabrina Heng、Kimberly R. Gryncel、Evan R. Kantrowitz

  DOI：10.1016/j.bmc.2009.04.030

  日期：2009.6

  The identification of a proper lead compound for fructose 1,6-bisphosphatase (FBPase) is a critical step in the process of developing novel therapeutics against type-2 diabetes. Herein, we have successfully generated a library of allosteric inhibitors against FBPase as potential anti-diabetic drugs, of which, the lead compound 1b was identified through utilizing a virtual high-throughput screening (vHTS) system, which we have developed. The thiazole-based core structure was synthesized via the condensation of alpha-bromoketones with thioureas and substituents on the two aryl rings were varied. 4c was found to inhibit pig kidney FBPase approximately fivefold better than 1b. In addition, we have also identified 10b, a tight binding fragment, which can be use for fragment-based drug design purposes. (C) 2009 Elsevier Ltd. All rights reserved.