5,8,11-Trioxa-2,14,16,18-tetrathiabicyclo<13.3.0>octadec-1(15)-en-17-thione | 98449-86-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,8,11-Trioxa-2,14,16,18-tetrathiabicyclo<13.3.0>octadec-1(15)-en-17-thione
• 英文别名: 5,8,11-trioxa-2,14,16,18-tetrathiabicyclo<13.3.0>octadec-1(15)ene-17-thione；5,8,11-trioxa-2,14,16,18-tetrathiabicyclo[13.3.0]octadec-1(15)ene-17-thione；5,8,11-trioxa-2,4,16,18-tetrathiabicyclo[13.3.0]octadec1(15)-ene-17-thione；2,14,16,18-tetrathiabicyclo[13.3.0]octadec-1-(15)-ene-17-thione；5,8,11-Trioxa-2,14,16,18-tetrathiabicyclo[13.3.0]octadec-1(15)-ene-17-thione
• CAS: 98449-86-6
• 化学式: C₁₁H₁₆O₃S₅
• 分子量: 356.576
• InChiKey: RXQOHVRFZLKDSY-UHFFFAOYSA-N

物化性质

• 熔点：
  70-74 °C
• 沸点：
  513.4±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,8,11-Trioxa-2,14,16,18-tetrathiabicyclo<13.3.0>octadec-1(15)-en-17-thione 在 sodium tetrahydroborate 、 lithium chloride 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 [5-(Hydroxymethyl)-2-(5,8,11-trioxa-2,14,16,18-tetrathiabicyclo[13.3.0]octadec-1(15)-en-17-ylidene)-1,3-dithiol-4-yl]methanol
  参考文献：
  名称：

  Dithia-Crown-Annelated Tetrathiafulvalene Disulfides:  Synthesis, Electrochemistry, Self-Assembled Films, and Metal Ion Recognition

  摘要：

  The synthesis and electrochemistry of a series of tetrathiafulvalene (TTF) and dithia-crown-TTF derivatives attached with one or two disulfide group(s) 7a-f are reported. The self-assembled monolayers (SAMs) of these TTF disulfides on gold were prepared and characterized by reflection-absorption infrared spectroscopy. The SAMs are extremely stable under a wide variety of conditions and over extended periods of time and show remarkable electrochemical stability upon repeated potential scans. SAMs of the crown-TTF disulfides 7c,d,f can recognize alkali metal ions, and the process can be monitored following the electrochemical potential shift of the surface-confined TTF group.

  DOI：

  10.1021/jo000115l
• 作为产物：
  描述：

  4,5-双(苯甲酰硫基)-1,3-二硫杂环戊烯-2-硫酮 、 1-溴-2-(2-(2-(2-溴乙氧基)乙氧基)乙氧基)乙烷 在 sodium ethanolate 作用下， 生成 5,8,11-Trioxa-2,14,16,18-tetrathiabicyclo<13.3.0>octadec-1(15)-en-17-thione
  参考文献：
  名称：

  Crown ether derivatives of tetrathiafulvalene. 1

  摘要：

  A synthetic procedure leading to derivatives of tetrathiafulvalene (TTF) incorporating crown ether ligands has been developed. The properties of such redox-active ionophores were studied by cyclic voltammetry (CV), plasma desorption mass spectrometry (PDMS), and H-1-NMR.

  DOI：

  10.1021/jo00050a010

文献信息

• Synthesis of annelated bis-crownethers.
  作者：Kim Christiansen、Jan Becher、Thomas Kruse Hansen

  DOI：10.1016/s0040-4039(00)79593-1

  日期：1992.5

  Symmetrical or unsymmetrical annelated bis-crownethers are prepared via the stepvise reaction of disodium-1,3-dithole-2-thione-4,5-dithiolate with a bis-alkylating reagent, BrCH2(CH2OCH2)nCH2Br.

  对称或不对称的退火双冠醚是通过1,3-二孔-2-硫代-4,5-二硫代二钠二钠与双烷基化试剂BrCH 2（CH 2 OCH 2）n CH 2 Br的逐步反应制备的。
• Synthesis and Metal Ion Complexation Studies of [60]Fullerene Derivatives of Tetrathiafulvalene Crown Ethers
  作者：Sheng-Gao Liu、Luis Echegoyen

  DOI：10.1002/1099-0690(200004)2000:7<1157::aid-ejoc1157>3.0.co;2-z

  日期：2000.4

  The synthesis of two novel [60]fullerene derivatives containing the electron donor tetrathiafulvalene and metal-complexing crown ethers is described, and their complexation ability with alkali metal cations is studied by solid-liquid extraction techniques, cyclic voltammetry and 1H NMR spectroscopy.

  描述了含有电子供体四硫富瓦烯和金属络合冠醚的两种新型 [60] 富勒烯衍生物的合成，并通过固液萃取技术、循环伏安法和 1 H NMR 光谱研究了它们与碱金属阳离子的络合能力。
• Crowned Tetrathiafulvalene Derivatives
  作者：Tetsuo Otsubo、Fumio Ogura

  DOI：10.1246/bcsj.58.1343

  日期：1985.4

  A new type of tetrathiafulvalene derivatives, fused with crown ethers, was prepared, which did not form a complex with sodium cation or TCNQ acceptor but readily with silver cation.

  制备了一种新型的与冠醚稠合的四硫富瓦烯衍生物，它不与钠阳离子或TCNQ受体形成络合物，但容易与银阳离子形成络合物。
• A New Tetrathiafulvalene−Anthracence Dyad Fusion with the Crown Ether Group:  Fluorescence Modulation with Na⁺ and C₆₀, Mimicking the Performance of an “AND” Logic Gate
  作者：Guanxin Zhang、Deqing Zhang、Yucheng Zhou、Daoben Zhu

  DOI：10.1021/jo052494u

  日期：2006.5.1

  In this Note, we describe a new TTF−anthracene dyad fusion with the crown ether unit. It is interesting to find that the fluorescence of this new dyad can be modulated with Na+ and C60, and its fluorescence intensity can be largely enhanced only in the presence of both Na+ and C60. Such fluorescence modulation behavior mimics the performance of a two-input “AND” logic gate.

  在本说明中，我们描述了一种带有冠醚单元的新型TTF-蒽二聚体。有趣的是，可以用Na +和C 60调节这种新二联体的荧光，并且只有在同时存在Na +和C 60的情况下，才能大大增强其荧光强度。这种荧光调制行为模仿了两输入“ AND”逻辑门的性能。
• A new crown ether annelated tetrathiafulvalene derivative with anthracene moiety as a sensor for Li+ and 1O2
  作者：Wei Liu、Jing-Hua Lu、Yong Ji、Jing-Lin Zuo、Xiao-Zeng You

  DOI：10.1016/j.tetlet.2006.03.055

  日期：2006.5

  A new crown ether annulated tetrathiafulvalene derivative with an anthracene moiety is shown to act as a dual-functional sensor for Li+ and 1O2, which may be useful in information processing at the molecular level.

  已显示具有蒽部分的新冠醚环化的四硫富瓦烯衍生物可作为Li +和1 O 2的双功能传感器，这可能在分子水平的信息处理中有用。