1,5-dimethyl-2-phenyl-4-(2-(5-(2-thienyl)thienyl)methylidene)amino-1H-pyrazo-3(2H)-one | 1417521-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-dimethyl-2-phenyl-4-(2-(5-(2-thienyl)thienyl)methylidene)amino-1H-pyrazo-3(2H)-one
• 英文别名: 4-(2,2'-bithiophen-5-ylmethyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one；1,5-Dimethyl-2-phenyl-4-[(5-thiophen-2-ylthiophen-2-yl)methylideneamino]pyrazol-3-one
• CAS: 1417521-52-8
• 化学式: C₂₀H₁₇N₃OS₂
• 分子量: 379.506
• InChiKey: UPMMYAYFVARRFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2-联噻吩-5-乙醛 、 4-氨基安替比林 以 乙醇 为溶剂， 以84%的产率得到1,5-dimethyl-2-phenyl-4-(2-(5-(2-thienyl)thienyl)methylidene)amino-1H-pyrazo-3(2H)-one
  参考文献：
  名称：

  用于分子内电荷转移的空间受阻安替比林的合成促进传感

  摘要：

  通过席夫碱缩合已经合成了一系列新的空间受阻的安替比林衍生物，用于潜在的荧光传感应用。它们的光学，热和电化学性质得到了充分表征。由于安替比林和位阻共轭部分之间的强大的分子内电荷转移的结果，观察到宽吸收光谱。对于大多数化合物，可观察到可逆的一个电子氧化对，咔唑，吩噻嗪和联噻吩官能化的衍生物在较高的正电势下表现出额外的可逆的一个单电子氧化过程。咔唑官能化的安替比林衍生物APCZ对Co 2+和Cu 2+具有良好的荧光感应，荧光强度提高了3.41倍，荧光量子产率提高了2倍。版权所有©2012 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.2948

文献信息

• The synthesis, crystal structure and enhanced blue fluorescence emission of novel antipyrine derivatives
  作者：Yi-Feng Sun、He-Ping Wang、Yong Chen、Zhi-Yong Chen、Ji-Kun Li

  DOI：10.1016/j.saa.2012.06.047

  日期：2012.11

  Four new antipyrine derivatives were synthesized and characterized by elemental analysis, FT-IR. H-1 NMR, C-13 NMR spectroscopy. and a representative compound 1b was confirmed based on the X-ray crystallographic analysis. The antipyrine-phenylboronic acid 1b crystallizes in the monoclinic space group P2(1)/c, and displays an E configuration about the C=N double bond. The absorption and fluorescence spectra of these compounds were investigated. Replacement of a six-membered phenyl group with a five-membered thienyl unit in the antipyrine derivatives resulted in a bathochromic shift approximately 21 nm, while the bithienyl system caused a strong bathochromic effect of 53 nm relative to the substituted phenyl groups. The bithienyl-antipyrine hybrid 1c displayed a turn-on fluorescence response to water, acetic acid (HOAc) and sulfuric acid (H2SO4) in ethanol solution, but no fluorescence response toward alkali. Whereas the free compound was very weakly fluorescent in ethanol, the addition of water, HOAc and H2SO4 leads to an appearance of strong blue fluorescence and a dramatic increase of emission intensity. (C) 2012 Elsevier B.V. All rights reserved.