9-phenyl-3,6,12,15-tetrathia-9-azaheptadecane | 148932-05-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 9-phenyl-3,6,12,15-tetrathia-9-azaheptadecane
• 英文别名: N,N-bis[2-(2-ethylsulfanylethylsulfanyl)ethyl]aniline
• CAS: 148932-05-2
• 化学式: C₁₈H₃₁NS₄
• 分子量: 389.715
• InChiKey: GFVQWIWXDUGCKM-UHFFFAOYSA-N

物化性质

• 沸点：
  547.0±45.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-phenyl-3,6,12,15-tetrathia-9-azaheptadecane 在 2,6-二甲基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 21.0h， 生成 (4-(bis(2-((2-(ethylthio)ethyl)thio)ethyl)amino)phenyl)(4,5-dimethoxy-2-nitrosophenyl)methanone
  参考文献：
  名称：

  使用ArgenCast光笼了解光解效率与金属结合之间的关系。

  摘要：

  已使用三甲基甲硅烷基三氟甲烷磺酸盐辅助制备了ArgenCast-1（1），这是一种利用无环聚硫醚3,6,12,15-tetrathia-9-azaheptadecane受体和4,5-二甲氧基-2-硝基苄基（DMNB）生色团的银光笼。亲电取代。与ArgenCast-1的金属结合研究揭示了与Ag（+），Hg（2+）和Cu（+）的相互作用，但在水性和有机溶剂中只有Ag（+）协同作用。ArgenCast-1金属络合物的解笼机理涉及光反应，该反应将硝基苯并吡咯转化为吸电子的亚硝基二苯甲酮，后者与与金属结合的苯胺氮原子发生共振相互作用。光解后的结构变化降低了氮孤对用于Ag（+）配位的可用性，但是Ag（+）与硫醚配体之间的强相互作用会减轻金属离子的释放。与关键的aci-硝基中间体的共振相互作用降低了ArgenCast-1的光解量子产率，因此筛选了几个基于萘基的硝基苄基作为DMNB的替代品。萘基Ag（+）

  DOI：

  10.1111/j.1751-1097.2012.01136.x
• 作为产物：
  描述：

  N,N-二羟乙基苯胺 在 吡啶 、 sodium ethanolate 作用下， 反应 16.0h， 生成 9-phenyl-3,6,12,15-tetrathia-9-azaheptadecane
  参考文献：
  名称：

  通过荧光寿命成像显微镜选择性检测活细胞中的 Cu+ 离子

  摘要：

  铜是生物体中必需的微量元素，其水平和定位由细胞机器精心管理。然而，如果调节不当，铜离子缺乏或过量会导致多种疾病。因此，拥有可靠的方法来检测、监测和可视化细胞中的这种金属非常重要。在此，我们报告了一种基于 BODIPY 的新型光学探针，该探针在与铜 (I) 结合后显示出荧光强度的开启，但在高浓度的其他生理相关金属离子存在的情况下则不会开启。更有趣的是，与铜（I）的结合导致新探针的荧光寿命发生显着变化，该探针可用于通过荧光寿命成像显微镜（FLIM）可视化活细胞溶酶体中的铜（I）库。

  DOI：

  10.1002/anie.202109349

文献信息

• Hydrazones Derived from Dithiamonoaza and Tetrathiamonoaza Analogs of Polyethers as Silver Ion Selective Ionophores: Syntheses, Proton-Dissociation Behaviors, and Metal Ion Complexing Properties in 1,4-Dioxane–Water Acidic Solution
  作者：Junichi Ishikawa、Hidefumi Sakamoto、Tamao Mizuno、Makoto Otomo

  DOI：10.1246/bcsj.68.3071

  日期：1995.11

  Cyclic and acyclic dithiamonoaza, tetrathiamonoaza, and tetrathiadiaza analogs of polyethers bearing a hydrazone moiety on nitrogen atom(s) were synthesized. Their acidity constants in 1,4-dioxane–water solution and stability constants of hydrazones derived from dithiamonoaza and tetrathiamonoaza analogs of polyethers for some heavy metal ions in same acidic media were measured spectrophotometrically

  合成了在氮原子上带有腙部分的聚醚的环状和非环状二硫单氮杂、四硫单氮杂和四硫二氮杂类似物。它们在 1,4-二氧六环 - 水溶液中的酸度常数和衍生自聚醚的二硫单氮杂和四硫单氮杂类似物的腙在相同酸性介质中对某些重金属离子的稳定性常数进行了分光光度法测量。环状和非环状四硫单氮杂系列的腙具有高度的 Ag+ 选择性络合性。
• Tracking Labile Copper Fluctuation <i>In Vivo</i>/<i>Ex Vivo</i>: Design and Application of a Ratiometric Near-Infrared Fluorophore Derived from 4-Aminostyrene-Conjugated Boron Dipyrromethene
  作者：Hongxia Xu、Shankun Yao、Yuncong Chen、Changli Zhang、Shuren Zhang、Hao Yuan、Zhongyan Chen、Yang Bai、Tao Yang、Zijian Guo、Weijiang He

  DOI：10.1021/acs.inorgchem.1c01779

  日期：2021.12.20

  infeasible. We proposed ratiometric optical imaging as an alternative to overcome these disadvantages, and a near-infrared (NIR) ratiometric sensor, BDPS1, was devised therefore by conjugating boron dipyrromethene (BODIPY) with 4-aminostyrene and modifying the 4-amino group as a Cu+ chelator. BDPS1 possessed an excitation ratiometric copper-sensing ability to show the ratio of NIR emission (710 nm) upon

  样本差异、组织依赖性背景荧光和散射以及样本位置和传感器浓度的偏差使得动物中不稳定铜波动的光学成像值得怀疑，并且样本之间的信号比较是不可行的。我们提出比率光学成像作为克服这些缺点的替代方案，并且通过将二吡咯亚甲基硼（BODIPY）与4-氨基苯乙烯共轭并将4-氨基修饰为Cu，设计了近红外（NIR）比率传感器BDPS1 。 +螯合剂。 BDPS1具有激发比率铜传感能力，显示 600 nm 激发时的 NIR 发射（710 nm）与 660 nm 激发时的 NIR 发射（710 nm）之比， F ex600 / F ex660 ，从 2.8 增加到 10.7。该传感器在其内部电荷转移（ICT；670 nm）和局部（581 nm）发射带中仍显示出相反的铜响应。使用该传感器的比例成像揭示了核器附近的更不稳定的铜区域，并且 HEK-293T 细胞比 MCF-7 细胞对铜孵育更敏感。利用该传感器的双激发比率
• Silver Selectivity of Novel Monoazapolythioether Derivatives Bearing a Hydrazone Group in the Solvent Extraction
  作者：Hidefumi Sakamoto、Junichi Ishkawa、Tamao Mizuno、Kunio Doi、Makoto Otomo

  DOI：10.1246/cl.1993.609

  日期：1993.4

  Novel acyclic and cyclic monoazapolythioether derivatives incorporating a substituted hydrazone group were synthesized. The acyclic and the cyclic monoazatetrathioether derivatives exhibited high Ag+ ion selectivity in the extraction with 1,2-dichloroethane. The monoazatetrathioether derivatives gave hypsochromic and bathochromic shifts in the visible absorption spectra when extracted Ag+ ion from the aqueous phase of varying acidities into the organic phase.

  合成了含有取代腙基的新型无环和环状单氮杂环硫醚衍生物。在用 1,2-二氯乙烷萃取时，无环和环状单氮杂环丁硫醚衍生物表现出较高的 Ag+ 离子选择性。将 Ag+ 离子从不同酸度的水相萃取到有机相中时，单氮杂环丁硫醚衍生物在可见吸收光谱中呈现出低色移和浴色移。
• Silver Ion Selective Fluoroionophores Based on Anthracene-Linked Polythiazaalkane or Polythiaalkane Derivatives
  作者：Junichi Ishikawa、Hidefumi Sakamoto、Shintaro Nakao、Hiroko Wada

  DOI：10.1021/jo9819584

  日期：1999.3.1

  A dozen novel fluoroionophores have been synthesized which are polythiazaalkane and polythiaalkane derivatives coupled with an anthracene moiety by methyl, carbonyl, or methylphenylene bridging groups. The protonation and metal ion complexation behavior of analogues were examined in 1,4-dioxane--water solutions spectrophotometrically and spectrophotofluorometrically. The fluoroionophores, 1, 2, 5, and 6 contain basic nitrogen atoms and quench the fluorescence in the free forms because of photoinduced electron transfer (PET) from a nitrogen atom to a photoexcited anthracene unit. The fluorescence was recovered by the protonation on the nitrogen atom. The fluorescence intensities of the other fluoroionophores used here were not dependent on the pH of the solution. On the complexation of the protonated fluoroionophores 1, 2, 5, and 6 with metal ions under the acidic condition, the fluorescence intensities were decreased by the addition of silver ion selectively. Under the same conditions, the other fluoroionophores exhibited a decrease of the fluorescence intensity with the addition of silver ion selectively. These results imply that the fluoroionophores could form complexes and release a proton from the nitrogen atom of the protonated fluoroionophores. The quenching of the fluorescence of the complexed fluoroionophores 3, 4, 7, and 8-12 could be caused by the interaction of a silver ion with a ct-electron of the anthracene unit. The degree of spectral change on the complexation with silver ion is primarily dependent on the strength of the interaction of the bound silver ion with nitrogen atom, far 1, 2, 5, and 6, or with a pi-electron of the anthracene unit, for 3, 4, 7, and 8-12.
• Ishikawa, Junichi; Sakamoto, Hidefumi; Wada, Hiroko, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1273 - 1279
  作者：Ishikawa, Junichi、Sakamoto, Hidefumi、Wada, Hiroko

  DOI：——

  日期：——