2-benzothiazolylmethylenetriphenylphosphorane | 1628-68-8

• 英文名称: 2-benzothiazolylmethylenetriphenylphosphorane
• 英文别名: 2-Benzthiazolyl-methylentriphenylphosphoran；2-[(triphenyl-λ⁵-phosphanylidene)-methyl]-benzothiazole；1,3-benzothiazol-2-ylmethylidene(triphenyl)-λ5-phosphane
• CAS: 1628-68-8
• 化学式: C₂₆H₂₀NPS
• 分子量: 409.491
• InChiKey: YGWGAUFIKSCRNI-UHFFFAOYSA-N

物化性质

• 熔点：
  163 °C
• 沸点：
  588.780±33.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.264±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-benzothiazolylmethylenetriphenylphosphorane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (Z)-2-[N-methyl-N-(2'-fluoroethyl)-4'-aminostyryl]benzothiazole
  参考文献：
  名称：

  Synthesis and in vitro evaluation of fluorinated styryl benzazoles as amyloid-probes

  摘要：

  The formation of proteinaceous aggregates is a pathognomonic hallmark of several neurodegenerative disorders such as Alzheimer's and Parkinson's diseases. To date, the final diagnostic for these diseases can only be achieved by immunostaining of post-mortem brain tissues with the commonly used congo red and Thioflavin T/S amyloid-dyes. The interest in developing amyloid-avid radioprobes to be used for protein aggregates imaging by positron emission tomography has grown substantialy, due to the promise in assisting diagnosis of these disorders. To this purpose, the present work describes the synthesis and characterization of four novel fluorinated styryl benzazole derivatives 1-4 by means of the Wittig reaction, as well as their in vitro evaluation as amyloid-probing agents. All compounds were obtained as mixtures of geometric E and Z isomers, with the preferable formation of the E isomer. Photoisomerization reactions allowed for the maximization of the minor Z isomers. The authentic 1-4E/Z isomers were isolated after purification by column chromatography under dark conditions. Profiting from the fluorescence properties of the different geometric isomers of 1-4, their binding affinities towards amyloid fibrils of insulin, alpha-synuclein and beta-amyloid peptide were also measured. These compounds share similarities with Thioflavin T, interacting specifically with fibrillary species with a red-shift in the excitation wavelengths along with an increase in the fluorescence emission intensity. Apparent binding constants were determined and ranged between 1.22 and 23.96 mu M-1. The present data suggest that the novel fluorinated styryl benzazole derivatives may prove useful for the design of F-18-labeled amyloid radioprobes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.065
• 作为产物：
  描述：

  2-benzothiazolylmethyltriphenylphosphonium chloride 在 potassium tert-butylate 作用下， 反应 3.0h， 以85%的产率得到2-benzothiazolylmethylenetriphenylphosphorane
  参考文献：
  名称：

  噻唑基亚甲基三苯基磷杂环戊烷及其苯并衍生物：合成乙烯基噻唑和乙烯基苯并的稳定和实用的wittig试剂：醛的二碳同系化

  摘要：

  标题的噻唑基磷烷是一种稳定但反应性很强的维蒂希型试剂，与各种醛反应后，可以很好的收率得到主要或仅作为异构体的乙烯基噻唑。而且，与文献报道不同，苯并噻唑基磷烷衍生物证明与醛反应。从噻唑核上进行甲酰基解封的乙烯基噻唑提供了两个碳均化的饱和醛。例如，这些乙烯基噻唑之一，即。β-苯基衍生物8f，证明在甲酰基解封3-苯基庚醛后加-丁基丁基锂锂得到。

  DOI：

  10.1016/s0040-4020(01)90345-x

文献信息

• 693. The synthesis of heterocyclic alkenes by the Horner reaction
  作者：E. B. Knott

  DOI：10.1039/jr9650003793

  日期：——
• DONDONI, ALESSANDRO;FANTIN, GIANCARLO;FOGAGNOLO, MARCO;MEDICI, ALESSANDRO+, TETRAHEDRON, 44,(1988) N 7, 2021-2031
  作者：DONDONI, ALESSANDRO、FANTIN, GIANCARLO、FOGAGNOLO, MARCO、MEDICI, ALESSANDRO+

  DOI：——

  日期：——