2,1-benzothiaselenol-3-one | 54996-54-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2,1-benzothiaselenol-3-one
• 英文别名: 3H-2,1-benzothiaselenol-3-one
• CAS: 54996-54-2
• 化学式: C₇H₄OSSe
• 分子量: 215.134
• InChiKey: PIWUZCBYDAVRCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,1-benzothiaselenol-3-one 、 正丁胺 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 7.0h， 以88%的产率得到2,2'-diselenobis(N-butylbenzamide)
  参考文献：
  名称：

  Cyclic Acyl Disulfides and Acyl Selenylsulfides as the Precursors for Persulfides (RSSH), Selenylsulfides (RSeSH), and Hydrogen Sulfide (H₂S)

  摘要：

  The reactions of three model compounds (1-3) for cyclic acyl disulfides and cyclic acyl selenylsulfides are studied. These compounds were found to be effective precursors for persulfides (RSSH) and selenylsulfides (RSeSH) upon reacting with nucleophilic species. They could also act as H2S donors when interacting with cellular thiols. The most interesting discovery was the generation of RSeSH from compound 3 under mild conditions. Selenylsulfides (RSeSH) are expected to be important regulating molecules involved in Sec-related redox signaling. The method of producing RSeSH should allow researchers to better understand the chemical biology of RSeSH.

  DOI：

  10.1021/acs.orglett.7b04005
• 作为产物：
  描述：

  苯甲酰氯,2-(氯硒代)- 在 sodium sulfide 、 丙酮 作用下， 生成 2,1-benzothiaselenol-3-one
  参考文献：
  名称：

  Lesser; Weiss, Chemische Berichte, 1924, vol. 57, p. 1079

  摘要：

  DOI：

文献信息

• Hydrogen Sulfide Mediated Tandem Reaction of Selenenyl Sulfides and Its Application in Fluorescent Probe Development
  作者：Yingying Wang、Chun-tao Yang、Shi Xu、Wei Chen、Ming Xian

  DOI：10.1021/acs.orglett.9b02844

  日期：2019.9.20

  A unique reaction between H2S and a selenenyl sulfide containing benzoate ester template was discovered. This reaction could be specifically triggered by H2S and lead to ester bond cleavage. The reaction was not affected by the presence of thiols such as glutathione and cysteine. With this reaction, a series of fluorescent probes were synthesized and evaluated. The probes exhibited high sensitivity/selectivity

  发现了H 2 S与含有苯甲酸酯模板的亚硒基硫化物之间的独特反应。H 2 S可能会特别引发该反应，并导致酯键断裂。该反应不受诸如谷胱甘肽和半胱氨酸之类的硫醇的存在的影响。通过该反应，合成并评估了一系列荧光探针。探针在缓冲液和细胞中均表现出对H 2 S的高灵敏度/选择性。
• A General Strategy for Development of Near‐Infrared Fluorescent Probes for Bioimaging
  作者：Wei Chen、Shi Xu、Jacob J. Day、Difei Wang、Ming Xian

  DOI：10.1002/anie.201710688

  日期：2017.12.22

  by easy modifications on the phenolic hydroxy group. Based on WR6, two NIR fluorescent turn‐on probes, WSP‐NIR and SeSP‐NIR, were devised for the detection of H2S. The probe SeSP‐NIR was applied in visualizing intracellular H2S. These dyes are expected to be useful fluorophore scaffolds in the development of new NIR probes for bioimaging.

  具有良好光物理性质的近红外（NIR）荧光染料在生物成像方面非常有用，但是这种染料仍然很少见。描述了通过用稠合的四氢喹喔啉环修饰Rhodol支架来开发一类独特的NIR染料。这些新染料显示出较大的斯托克斯位移（> 110 nm）。其中，WR3，WR4，WR5和WR6在水溶液中显示出高的荧光量子产率和出色的光稳定性。而且，它们的荧光特性可通过对酚羟基的简单修饰来调节。基于WR6，二NIR荧光接通探针，WSP-NIR和SESP-NIR，被设计成用于检测H的2 S.探针SESP-NIR在可视化细胞内H为施加2S.预期这些染料将在开发用于生物成像的新型NIR探针中用作有用的荧光支架。
• Understanding Reactivity and Assembly of Dichalcogenides: Structural, Electrostatic Potential, and Topological Analyses of 3<i>H</i>-1,2-Benzodithiol-3-one and Selenium Analogs
  作者：Rahul Shukla、Arun Dhaka、Emmanuel Aubert、Vishnu Vijayakumar-Syamala、Olivier Jeannin、Marc Fourmigué、Enrique Espinosa

  DOI：10.1021/acs.cgd.0c00961

  日期：2020.12.2

  that CD···CC interactions drive molecular orientation in molecular assembly. Strength of ChB is measured in terms of the topological properties of ρ(r), whereas the intensity of the electrophilic···nucleophilic interaction is monitored by [(L/ρ)CC – (L/ρ)CD]/dCC···CD2. The σ-hole in side-on conformation forms the strongest ChB interactions in molecular assembly. Reactivity of molecules against nucleophilic

  用一系列的3 H -1,2-苯并二硫基-3-（thi）one衍生物及其（混合的）硒化类似物研究了分子组装和反应性。单体的静电势计算结果表明，二卤化氢Ch-Ch键（Ch = S，Se）周围有三个σ孔区域，一侧朝上，两个沿结合方向。电子密度ρ（r）的拓扑分析指出了Ch–Ch键的弱性质。σ孔和孤对区是根据硫族元素原子的价壳中的电荷耗尽（CD）和电荷浓度（CC）位点描述的。而CD和CC位点的特征在于拓扑临界点大号（[R）=-∇ 2 ρ（ř），它们的亲电和亲核能力通过相应的L /ρ值来衡量。在晶体结构中，每个硫族元素键（ChB）都包含一个σ孔区域，并显示出CD···CC相互作用，该相互作用与CD和CC位置所属的原子的核间方向对齐。对于每个晶体结构中的所有ChB相互作用，排列均同时保持，表明CD···CC相互作用驱动分子组装中的分子取向。ChB的强度是根据ρ（r）的拓扑性质来衡量的，而亲电···亲核相互作用的强度则通过[（L
• A ratiometric fluorescent probe for hydrogen sulfide based on the nucleophilic substitution-cyclization of diselenides
  作者：Caihong Zhang、Bo Peng、Wei Chen、Shaomin Shuang、Ming Xian、Chuan Dong

  DOI：10.1016/j.dyepig.2015.06.003

  日期：2015.10

  A new ratiometric fluorescence probe for hydrogen sulfide is developed. The design was based on a H2S-mediated diselenide cleavage and intramolecular cyclization to release the fluorophore. The probe showed high selectivity and sensitivity for H2S over other reactive sulfur species and was successfully applied for the detection of H2S in bovine plasma and bioimaging in live cells.

  开发了一种新型的硫化氢比例荧光探针。该设计基于H 2 S介导的二硒化物裂解和分子内环化以释放荧光团。该探针对H 2 S的选择性和灵敏度优于其他反应性硫，并且已成功用于牛血浆中H 2 S的检测以及活细胞的生物成像。
• Synthesis of 2-Acyl- and 2-Sulfonylbenzisoselenazol-3(2H)-ones
  作者：Sungano Mhizha、Jacek Młochowski

  DOI：10.1080/00397919708005029

  日期：1997.1

  Synthesis of two new groups of organoselenium compounds: 2-acyl-and sulfonylbenzisoselenazol-3(2H)-ones (3,4), potential immunostimulants, in two alternative ways was elaborated. One of them was based on the reaction of 2-chlorobenzoyl chloride(2) with primary amides while the second one involved N-acylation or N-sulfonylation of benzisoselenazol-3(2H)-one (5) with acid chlorides. Two exceptions from general reaction of dichloride 2 with amides were observed. Thioacetamide produced 2,1-benzothiaselenophenone (6), and urea gave 6,7-benzo-2,4-diaza-1-selenacyclohepta-3,5-dione (7).