bis[2-(3-phenyl-thioureido)ethyl]disulfide | 15267-16-0

• 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: bis[2-(3-phenyl-thioureido)ethyl]disulfide
• 英文别名: 1,1'-(Dithiodiaethylen)-2,2'-bis(3-phenyl-thioharnstoff)；N-(2-((2-((Anilinocarbothioyl)amino)ethyl)dithio)ethyl)-N'-phenylthiourea；1-phenyl-3-[2-[2-(phenylcarbamothioylamino)ethyldisulfanyl]ethyl]thiourea
• CAS: 15267-16-0
• 化学式: C₁₈H₂₂N₄S₄
• 分子量: 422.663
• InChiKey: YUMZALXGEIVNAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯基-4,5-二氢-1,3-噻唑-2-胺 生成 bis[2-(3-phenyl-thioureido)ethyl]disulfide
  参考文献：
  名称：

  2-Amino-2-thiazoline. IV. Ring-opening of 2-amino-2-thiazolines and 2-amino-2-selenazoline with hydrogen sulfide to form thiourea derivatives

  摘要：

  DOI：

  10.1021/jo01266a102

文献信息

• Enhanced Sensitivity and Selectivity of Chemosensor for Malonate by Anchoring on Gold Nanoparticles
  作者：Yanyun Liu、Yun Liu、Zhongshi Liang、Xiangyang Li、Shunying Liu、Jiahui Yu

  DOI：10.1002/cjoc.201190118

  日期：2011.3

  assembled on gold nanoparticles was synthesized. The preorganized system possesses phenylthiourea units for the spectrophotometric sensing of dicarboxylates, especially malonate, based on changes in the surface plasmon absorption of the gold nanoparticles (GNPs). The intensity of the absorbance band increases gradually with the concentration of dicarboxylates increasing. But such an ion‐selective change

  合成了一种新型的有机-无机纳米杂化受体4，该受体经双硫脲臂官能化，然后组装在金纳米颗粒上。基于金纳米颗粒（GNP）的表面等离激元吸收的变化，预组织的系统具有苯硫脲单元，用于分光光度法感测二羧酸盐（尤其是丙二酸）。吸收带的强度随着二羧酸盐浓度的增加而逐渐增加。但是，在单硫脲修饰的GNP，受体3和游离受体2进行的对照试验中，未观察到等离激元带中的离子选择性变化。如从定量滴定得出的缔合常数所示，受体4可以选择性识别较短碳链的二羧酸根阴离子，并且对丙二酸具有最高的亲和力。通过1 H NMR和UV-vis光谱法评估了受体4阴离子的相互作用特性。
• Introduction of a Disulfide Bond as a Key Element of Acyclic Bis-Thiourea-Type Anion Receptors
  作者：Kentaro Tomita、Toshio Ishioka、Akira Harata

  DOI：10.1246/bcsj.20130267

  日期：2014.3.15

  This article shows that a difference in the building blocks of the molecular framework, C–C to S–S, results in a significant influence on its optical properties. Acyclic anion receptors, bis2-[3-(substituted)thioureido]ethyl} disulfides were newly synthesized, and their optical properties in response to complex formation with an acetate ion were compared with those of a hexamethylene framework between two thioureido groups. Quantum chemical calculations suggested that receptors fold their molecular framework around disulfide because of the presence of the intramolecular hydrogen bonding between two N,N′-disubstituted thioureas. The complex of the receptor and the acetate ion with 1:1 stoichiometry consists of the coordination of two thioureido groups to the acetate via hydrogen bonds. This complex formation is accompanied by a dissociation of intramolecular hydrogen bonding and rotation of one side of the thioureido group. These circumstances of conformational changes in the molecular framework functioned by switching on and off the excimer fluorescence of the 1-pyrenylmethyl derivative.

  本文表明，分子框架的组成部分（C-C 到 S-S）的差异对其光学性质产生重大影响。新合成了无环阴离子受体双2-[3-(取代)硫脲基]乙基}二硫化物，并将其响应与乙酸根离子形成络合物的光学性质与两个硫脲基之间的六亚甲基骨架的光学性质进行了比较。量子化学计算表明，由于两个 N,N'-二取代硫脲之间存在分子内氢键，受体将其分子框架折叠在二硫键周围。受体和乙酸根离子按 1:1 化学计量形成的复合物由两个硫脲基通过氢键与乙酸根配位组成。这种复合物的形成伴随着分子内氢键的解离和硫脲基一侧的旋转。分子框架中构象变化的这些情况通过打开和关闭 1-芘基甲基衍生物的准分子荧光来发挥作用。
• 2-Amino-2-thiazoline. IV. Ring-opening of 2-amino-2-thiazolines and 2-amino-2-selenazoline with hydrogen sulfide to form thiourea derivatives
  作者：Daniel L. Klayman、Peter T. McIntyre

  DOI：10.1021/jo01266a102

  日期：1968.2