methyl (E)-4-((2-(phenylsulfonyl)-hydrazono)methyl)benzoate | 1333317-92-2

• 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: methyl (E)-4-((2-(phenylsulfonyl)-hydrazono)methyl)benzoate
• 英文别名: methyl 4-{(E)-[2-(phenylsulfonyl)hydrazinylidene]methyl}benzoate；methyl 4-[(E)-(benzenesulfonylhydrazinylidene)methyl]benzoate
• CAS: 1333317-92-2
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: RMTBJOUEBAUMMZ-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-((2-(phenylsulfonyl)-hydrazono)methyl)benzoate 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 4-(2-(4-hydroxyphenyl)-2H-tetrazol-5-yl)benzoic acid
  参考文献：
  名称：

  Spiro[2.3]hex-1-ene 的设计，一种用于超快光点击化学的可遗传编码的双应变烯烃

  摘要：

  反应性但稳定的烯烃报告分子通过基于环加成的生物正交反应为研究快速生物过程提供了一种简便的途径。在这里，我们报告了一种用于加速光点击化学的应变螺环烯烃 spiro[2.3]hex-1-ene (Sph) 的设计和合成，以及使用野生型通过琥珀密码子抑制将其位点特异性引入蛋白质吡咯赖氨酰-tRNA 合成酶/tRNACUA 对。由于其高环应变和减少的空间位阻，Sph 在光点击化学中表现出快速反应动力学（k2 高达 34 000 M–1 s–1），并提供快速（<10 s）生物正交蛋白质标记。

  DOI：

  10.1021/ja5012542

文献信息

• Genetically Encoded Cyclopropene Directs Rapid, Photoclick-Chemistry-Mediated Protein Labeling in Mammalian Cells
  作者：Zhipeng Yu、Yanchao Pan、Zhiyong Wang、Jiangyun Wang、Qing Lin

  DOI：10.1002/anie.201205352

  日期：2012.10.15

  We just click: Genetic incorporation of a cyclopropene amino acid CpK (see scheme) site‐specifically into proteins in E. coli and mammalian cells was achieved using an orthogonal aminoacyl‐tRNA synthetase/tRNACUA pair (CpKRS/MbtRNACUA). Cyclopropene exhibited fast reaction kinetics in the photoclick reaction and allowed rapid (ca. 2 min) labeling of proteins.

  我们只需点击：使用正交氨酰-tRNA 合成酶/tRNA CUA对（CpKRS/ Mb tRNA CUA），将环丙烯氨基酸 CpK（参见方案）基因位点特异性地整合到大肠杆菌和哺乳动物细胞中的蛋白质中。环丙烯在光点击反应中表现出快速反应动力学，并允许快速（约 2 分钟）标记蛋白质。
• A tetrazole-ene photoactivatable fluorophore with improved brightness and stability in protic solution
  作者：Yi-Kang Zhang、Meng Li、Lan Ruan、Peng An

  DOI：10.1039/d2cc03482d

  日期：——

  The pyrazoline fluorophore, generated by photoinduced tetrazole-ene cycloaddition, shows faint fluorescence in protic solvents. To suppress this fluorescence-quenching, we rationally designed a series of substituted diaryl tetrazoles at the N-side phenyl ring to produce a tetrazole-ene based photoactivatable fluorophore. Spectroscopic and cellular imaging studies demonstrated that the version of the

  通过光诱导四唑-烯环加成产生的吡唑啉荧光团在质子溶剂中显示出微弱的荧光。为了抑制这种荧光猝灭，我们在 N 侧苯环上合理地设计了一系列取代的二芳基四唑，以产生基于四唑烯的可光活化荧光团。光谱和细胞成像研究表明，具有双（三氟甲基）苯取代基的荧光团具有显着增强的亮度和光稳定性。
• Fluorogenic, Two-Photon-Triggered Photoclick Chemistry in Live Mammalian Cells
  作者：Zhipeng Yu、Tymish Y. Ohulchanskyy、Peng An、Paras N. Prasad、Qing Lin

  DOI：10.1021/ja407867a

  日期：2013.11.13

  The tetrazole-based photoclick chemistry has provided a powerful tool to image proteins in live cells. To extend photoclick chemistry to living organisms with improved spatiotemporal control, here we report the design of naphthalene-based tetrazoles that can be efficiently activated by two-photon excitation with a 700 nm femtosecond pulsed laser. A water-soluble, cell-permeable naphthalene-based tetrazole was identified that reacts with acrylamide with the effective two-photon cross-section for the cycloaddition reaction determined to be 3.8 GM. Furthermore, the use of this naphthalene-tetrazole for real-time, spatially controlled imaging of microtubules in live mammalian cells via the fluorogenic, two-photon-triggered photoclick chemistry was demonstrated.
• DETECTION OF ACRYLIC ACID
  申请人：AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH

  公开号：US20170121752A1

  公开（公告）日：2017-05-04

  There is provided a method for detecting the presence or absence of acrylic acid or its derivatives thereof in a sample, the method comprising the steps of: (a) introducing a probe comprising a diaryltetrazole compound to the sample; (b) exposing said sample to light; and (c) detecting the presence or absence of acrylic acid or its derivatives thereof in the sample based on fluorescence emitted by the sample after step (c).
• Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry
  作者：Zhipeng Yu、Qing Lin

  DOI：10.1021/ja5012542

  日期：2014.3.19

  reporters offer a facile route to studying fast biological processes via the cycloaddition-based bioorthogonal reactions. Here, we report the design and synthesis of a strained spirocyclic alkene, spiro[2.3]hex-1-ene (Sph), for an accelerated photoclick chemistry, and its site-specific introduction into proteins via amber codon suppression using the wild-type pyrrolysyl-tRNA synthetase/tRNACUA pair.

  反应性但稳定的烯烃报告分子通过基于环加成的生物正交反应为研究快速生物过程提供了一种简便的途径。在这里，我们报告了一种用于加速光点击化学的应变螺环烯烃 spiro[2.3]hex-1-ene (Sph) 的设计和合成，以及使用野生型通过琥珀密码子抑制将其位点特异性引入蛋白质吡咯赖氨酰-tRNA 合成酶/tRNACUA 对。由于其高环应变和减少的空间位阻，Sph 在光点击化学中表现出快速反应动力学（k2 高达 34 000 M–1 s–1），并提供快速（<10 s）生物正交蛋白质标记。