2-(2,2'-bithiophen-5-yl)benzo[d]thiazole | 34967-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2-(2,2'-bithiophen-5-yl)benzo[d]thiazole
• 英文别名: 2-[2,2']bithiophenyl-5-yl-benzothiazole；2-(5-thiophen-2-ylthiophen-2-yl)-1,3-benzothiazole
• CAS: 34967-83-4
• 化学式: C₁₅H₉NS₃
• 分子量: 299.441
• InChiKey: RXYVQASOTAKQRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2-联噻吩-5-乙醛 、 2-氨基苯硫醇 以 二甲基亚砜 为溶剂， 反应 1.0h， 以92%的产率得到2-(2,2'-bithiophen-5-yl)benzo[d]thiazole
  参考文献：
  名称：

  新型荧光2-（2'，2″-噻吩基）-1,3-苯并噻唑的合成

  摘要：

  通过使各种5-甲酰基-5'-烷氧基-或5-甲酰基-5'- N，N-二烷基氨基-2,2'-联噻吩与邻-氨基苯硫醇良好或优异地反应来合成Bithienyl-1,3-苯并噻唑衍生物产量。评估这些化合物的荧光性质。它们在450-600 nm区域显示强荧光，并具有高量子产率和较大的斯托克斯位移。

  DOI：

  10.1016/j.tetlet.2004.02.048

文献信息

• Synthesis of new fluorescent 2-(2′,2″-bithienyl)-1,3-benzothiazoles
  作者：Rosa M.F. Batista、Susana P.G. Costa、M.Manuela M. Raposo

  DOI：10.1016/j.tetlet.2004.02.048

  日期：2004.3

  Bithienyl-1,3-benzothiazole derivatives were synthesised by reacting various 5-formyl-5′-alkoxy- or 5-formyl-5′-N,N-dialkylamino-2,2′-bithiophenes with ortho-aminobenzenethiol in good to excellent yields. Evaluation of the fluorescence properties of these compounds was carried out. They show strong fluorescence in the 450–600 nm region, as well as high quantum yields and large Stokes’ shifts.

  通过使各种5-甲酰基-5'-烷氧基-或5-甲酰基-5'- N，N-二烷基氨基-2,2'-联噻吩与邻-氨基苯硫醇良好或优异地反应来合成Bithienyl-1,3-苯并噻唑衍生物产量。评估这些化合物的荧光性质。它们在450-600 nm区域显示强荧光，并具有高量子产率和较大的斯托克斯位移。
• Room Temperature Anhydrous Suzuki–Miyaura Polymerization Enabled by C−S Bond Activation
  作者：Xuan Wen、Wenbin Xie、Yawen Li、Xiaoying Ma、Zhaoying Liu、Xiao Han、Kaikai Wen、Fengjiao Zhang、Yuze Lin、Qinqin Shi、Aidong Peng、Hui Huang

  DOI：10.1002/anie.202309922

  日期：2023.10.2

  cross-coupling reaction between (hetero)aryl boronic esters and aryl sulfides was explored, of which universality was exemplified with thirty small molecules and twelve alternating conjugated polymers. Mechanism studies revealed the importance of room temperature and anhydrous condition in reducing the homocoupling defects and enhancing the optoelectronic properties of the conjugated polymers.

  探索了（杂）芳基硼酸酯和芳基硫醚之间的无水室温 CAS-Suzuki-Miyaura 交叉偶联反应，其通用性以 30 种小分子和 12 种交替共轭聚合物为例。机理研究揭示了室温和无水条件在减少自偶联缺陷和增强共轭聚合物光电性能方面的重要性。
• Synthesis and evaluation of novel benzothiazole derivatives based on the bithiophene structure as potential radiotracers for β-amyloid plaques in Alzheimer’s disease
  作者：Meng-Chao Cui、Zi-Jing Li、Rui-Kun Tang、Bo-Li Liu

  DOI：10.1016/j.bmc.2010.02.002

  日期：2010.4

  In this study, six novel benzothiazole derivatives based on the bithiophene structure were developed as potential beta-amyloid probes. In vitro binding studies using A beta aggregates showed that all of them demonstrated high binding affinities with K-i values ranged from 0.11 to 4.64 nM. In vitro fluorescent staining results showed that these compounds can intensely stained A beta plaques within brain sections of APP/PS1 transgenic mice, animal model for AD. Two radioiodinated compounds [I-125]-2-(5'-iodo-2,2'-bithiophen-5-yl)-6-methoxybenzo[d]thiazole [I-125]10 and [I-125]-2-(2,2'-bithiophen-5-yl)-6-iodobenzo[d]thiazole [I-125]13 were successfully prepared through an iododestannylation reaction. Furthermore, in vitro autoradiography of the AD model mice brain sections showed that both [I-125]10 and [I-125]13 labeled the A beta plaques specifically with low background. In vivo biodistribution studies in normal mice indicated that [I-125]13 exhibited high brain uptake (3.42% ID/g at 2 min) and rapid clearance from the brain (0.53% ID/g at 60 min), while [I-125]10 showed lower brain uptake (0.87% ID/g at 2 min). In conclusion, these preliminary results of this study suggest that the novel radioiodinated benzothiazole derivative [I-125]13 may be a candidate as an in vivo imaging agent for detecting beta-amyloid plaques in the brain of AD patients. (C) 2010 Elsevier Ltd. All rights reserved.