4-((2-tosylhydrazono)methyl)benzoic acid | 363575-75-1

• 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-((2-tosylhydrazono)methyl)benzoic acid
• 英文别名: 4-[[(4-Methylphenyl)sulfonylhydrazinylidene]methyl]benzoic acid
• CAS: 363575-75-1
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: WUKMQXRMGZTKNP-UHFFFAOYSA-N

物化性质

• 沸点：
  525.7±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  95.83
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-((2-tosylhydrazono)methyl)benzoic acid 在 盐酸 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.33h， 生成 Tet(I)-FF
  参考文献：
  名称：

  Photodegradable Supramolecular Hydrogels with Fluorescence Turn-On Reporter for Photomodulation of Cellular Microenvironments

  摘要：

  Photodegradable hydrogels that allow 3D encapsulation of cells are important biomaterials to modulate cellular microenvironments with temporal and spatial resolution. Herein we report a photodegradable hydrogel formed by the self-assembly of short peptides modified with a novel phototrigger. The phototrigger is a biaryl-substituted tetrazole moiety that, upon mild light irradiation, undergoes rapid intramolecular photoclick ligation to form a highly fluorescent pyrazoline moiety. Short peptides linked with a tetrazole-containing moiety, Tet(I) or Tet(II), are able to self-assemble into hydrogels, among which the Tet(I)-GFF and Tet(II)-GFRGD gels show good mechanical strength and biocompatibility for 3D encapsulation and prolonged culture of live cells. The phototriggered tetrazole-to-pyrazoline transformation generates a highly fluorescent reporter and induces the disassembly of the hydrogel matrix by disturbing the balance between hydrophilic interaction and it-if stacking of the self-assembled system. Photomodulation of cellular microenvironments was demonstrated not only for the cells grown on top of the gel but also for stem cells encapsulated inside the hydrogels.

  DOI：

  10.1021/ja409000b
• 作为产物：
  描述：

  对醛基苯甲酸 、 对甲苯磺酰肼 以 乙醇 为溶剂， 以35 %的产率得到4-((2-tosylhydrazono)methyl)benzoic acid
  参考文献：
  名称：

  优化 2,5-二芳基四唑的合成：反应溶剂的决定性选择

  摘要：

  芳基重氮盐与芳基磺酰腙在乙醇-吡啶中的反应是合成 2,5-二芳基四唑的简单、无金属的路线。然而，难溶于这种极性介质的聚芳族前体很难使用。我们在这里表明，在许多情况下，选择另一种反应溶剂（例如丙酮-吡啶）可以完美控制反应并导致目标四唑的自发沉淀。

  DOI：

  10.1016/j.tet.2023.133560

文献信息

• Star polymer synthesis via λ-orthogonal photochemistry
  作者：Kai Hiltebrandt、Michael Kaupp、Edgar Molle、Jan P. Menzel、James P. Blinco、Christopher Barner-Kowollik

  DOI：10.1039/c6cc03848d

  日期：——

  We introduce a light induced sequence enabling 𝝀-orthogonal star polymer formation via an arms-first approach, based on an [small alpha],[small omega]-functional polymer carrying tetrazole and o-methyl benzaldehyde moieties, which upon irradiation can...

  我们引入了一种光诱导序列，该序列使得基于携带有四唑和邻甲基苯甲醛部分的α，α，α官能小聚合物能够在辐射下通过臂先方法形成β-正交星形聚合物。 。
• Photoinducible Oncometabolite Detection
  作者：Rhushikesh A. Kulkarni、Chloe A. Briney、Daniel R. Crooks、Sarah E. Bergholtz、Chandrasekhar Mushti、Stephen J. Lockett、Andrew N. Lane、Teresa W.‐M. Fan、Rolf E. Swenson、W. Marston Linehan、Jordan L. Meier

  DOI：10.1002/cbic.201800651

  日期：2019.2

  Dysregulated levels of “oncometabolites” fuel cancer by directly stimulating oncogenic signaling. Here we report an optimized photoinducible 1,3‐dipolar cycloaddition that can be used to profile dysregulated fumarate metabolism in patient tumor samples, and demonstrate its application in imaging experiments. This intersection of bioorthogonal chemistry and metabolite reactivity could have future application

  “致癌代谢物”水平失调通过直接刺激致癌信号而加剧癌症。在这里，我们报告了一种优化的光诱导1,3-偶极环加成，可用于分析患者肿瘤样本中失调的富马酸盐代谢，并证明其在成像实验中的应用。生物正交化学和代谢物反应性的这种交叉可能在代谢物分析、成像和诊断方面具有未来的应用。
• <i>λ</i>-Orthogonal Pericyclic Macromolecular Photoligation
  作者：Kai Hiltebrandt、Thomas Pauloehrl、James P. Blinco、Katharina Linkert、Hans G. Börner、Christopher Barner-Kowollik

  DOI：10.1002/anie.201410789

  日期：2015.2.23

  A photochemical strategy enabling λ‐orthogonal reactions is introduced to construct macromolecular architectures and to encode variable functional groups with site‐selective precision into a single molecule by the choice of wavelength. λ‐Orthogonal pericyclic reactions proceed independently of one another by the selection of functional groups that absorb light of specific wavelengths. The power of

  引入了实现λ正交反应的光化学策略，以构建大分子结构，并通过选择波长将位点选择精度的可变功能基团编码为单个分子。通过选择吸收特定波长的光的官能团，λ-正交周环反应彼此独立地进行。等摩尔量的马来酰亚胺与两种带有不同马来酰亚胺反应性端基的聚合物（即光活性二烯（光烯醇）和腈亚胺（四唑））的一锅反应显示了新概念的强大功能。在λ= 310-350 nm的选择性照射下，任何马来酰亚胺（或活化的烯）封端的化合物都仅与光烯醇官能团聚合物发生反应。完成光烯醇的转化后，随后在λ= 270-310 nm处的辐照激活了四唑基团与功能烯的反应。复杂的马来酰亚胺，官能烯和聚合物与中心聚合物支架的λ正交点击反应表明了该方法的多功能性。
• A supramolecular hydrogel as a carrier to deliver microRNA into the encapsulated cells
  作者：Jinbo Li、Romain Kooger、Mingtao He、Xiao Xiao、Li Zheng、Yan Zhang

  DOI：10.1039/c4cc00156g

  日期：——

  A supramolecular hydrogel formed by dipeptide Gly-Ala linked with biphenyl-substituted tetrazole serves not only as a 3D matrix for live cells, but also as a carrier to deliver microRNA into the encapsulated cells.

  由与联苯取代的四唑连接的二肽Gly-Ala形成的超分子水凝胶不仅充当活细胞的3D基质，而且还充当将microRNA传递到封装细胞中的载体。
• Photodegradable Supramolecular Hydrogels with Fluorescence Turn-On Reporter for Photomodulation of Cellular Microenvironments
  作者：Mingtao He、Jinbo Li、Subee Tan、Ruzhi Wang、Yan Zhang

  DOI：10.1021/ja409000b

  日期：2013.12.18

  Photodegradable hydrogels that allow 3D encapsulation of cells are important biomaterials to modulate cellular microenvironments with temporal and spatial resolution. Herein we report a photodegradable hydrogel formed by the self-assembly of short peptides modified with a novel phototrigger. The phototrigger is a biaryl-substituted tetrazole moiety that, upon mild light irradiation, undergoes rapid intramolecular photoclick ligation to form a highly fluorescent pyrazoline moiety. Short peptides linked with a tetrazole-containing moiety, Tet(I) or Tet(II), are able to self-assemble into hydrogels, among which the Tet(I)-GFF and Tet(II)-GFRGD gels show good mechanical strength and biocompatibility for 3D encapsulation and prolonged culture of live cells. The phototriggered tetrazole-to-pyrazoline transformation generates a highly fluorescent reporter and induces the disassembly of the hydrogel matrix by disturbing the balance between hydrophilic interaction and it-if stacking of the self-assembled system. Photomodulation of cellular microenvironments was demonstrated not only for the cells grown on top of the gel but also for stem cells encapsulated inside the hydrogels.