1,13-双(8-喹啉)-1,4,7,10,13-五噁十三烷 | 57310-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1,13-双(8-喹啉)-1,4,7,10,13-五噁十三烷
• 中文别名: 1,13-双(8-喹啉基)-1,4,7,10,13-五氧代十三烷
• 英文名称: kryptofix 5
• 英文别名: 1,13-bis(8-quinolyl)-1,4,7,10,13-pentaoxatridecane；1,11-Bis-(8-chinolyloxy)-3,6,9-trioxaundecan；1,11-Bis(8-quinolinyloxy)-3,6,9-trioxaundecane；8-[2-[2-[2-(2-quinolin-8-yloxyethoxy)ethoxy]ethoxy]ethoxy]quinoline
• CAS: 57310-75-5
• 化学式: C₂₆H₂₈N₂O₅
• mdl: MFCD00040469
• 分子量: 448.519
• InChiKey: GHYUCQLUMXYVRT-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 安全说明：
  S22,S24/25
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1,13-双(8-喹啉)-1,4,7,10,13-五噁十三烷 在 calcium chloride 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  A Conductometric Study of Complexation Reactions between Kryptofix5 with Al3+, Fe3+, Cu2+, and Ca2+ Metal Cations in Acetonitrile–Ethanol Binary Solvent Solutions

  摘要：

  DOI：

  10.1134/s003602442013021x
• 作为试剂：
  描述：

  2-羟基-4-氧代-1H-喹啉-3-甲腈 在 sodium azide 、 1,13-双(8-喹啉)-1,4,7,10,13-五噁十三烷 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 5-azidotetrazolo[1,5-a]quinoline-4-carbonitrile
  参考文献：
  名称：

  Regioselective Azidation of 2,4-Dichloroquinolines

  摘要：

  Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazolo[1,5-a]quinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chloro-tetrazolo[1,5-a]quinolines (5g-i). When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazolo[1,5-a]quinolines (5a-i) are obtained. Structural assignments of 3 and 5 have been carried out by C-13-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9). It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.

  DOI：

  10.1002/prac.19943360407

文献信息

• Kryptofix 5 as an inexpensive and efficient ligand for the palladium-catalyzed Mizoroki-Heck reaction
  作者：Barahman Movassagh、Shabnam Ranjbari

  DOI：10.1002/aoc.4224

  日期：2018.4

  A novel complex of PdCl2 with a multidentate cryptand ligand, Kryptofix 5, has been prepared and characterized by various techniques including 1H‐ and 13C NMR spectroscopy, Fourier transform infrared (FT‐IR), Raman, ultraviolet and visible (UV‐VIS) spectroscopy, inductively coupled plasma (ICP), CHN elemental and energy dispersive X‐ray analysis (EDX). This heat‐ and air‐stable complex was utilized

  制备了一种具有多齿隐配体配体的新型PdCl 2复合物Kryptofix 5，并通过1 H-和13 C NMR光谱，傅立叶变换红外（FT-IR），拉曼，紫外和可见（UV- VIS）光谱，电感耦合等离子体（ICP），CHN元素和能量色散X射线分析（EDX）。这种热和空气稳定的络合物被用作芳基卤化物与各种烯烃的Mizoroki-Heck反应的高活性催化剂。有趣的是，发现芳基溴化物和芳基碘化物可以在130°C的条件下在10分钟内有效地与末端烯烃交联。此外，反应性最低的芳基氯化物与苯乙烯反应，以可接受的收率获得所需的产物。
• Übergangsmetallkomplexe mit Schwefelliganden CXXIV. Koordination von C- und S-Liganden an Metall—Carben—Thiolat-Fragmente [M(‘S2C’)] [M = NiII, PdII, PtII; ‘S2C’2− = 1,3-Imidazolidinyl-N,N′-bis(2-benzolthiolat)(2 −)]. [M(L)(‘S2C’)]-Komplexe mit L = CN−, CH3−, COCH3−, CNBu, CR2, SH− und SR− (R = Et, Ph, o-C6H4NH2)
  作者：Dieter Sellmann、Christof Allmann、Frank Heinemann、Falk Knoch、Jörg Sutter

  DOI：10.1016/s0022-328x(97)00073-9

  日期：1997.8

  parent complexes [M(‘S2C’)]2. The methyl complex [Li(4-crown-4)2][Ni(CH3)(‘S2C’)] (5) is one of the rare examples in which a methyl ligand binds to an [NiS] center. While the parent complex [Ni(‘S2C’)]2 · DMF (1) proved unreactive towards CO, 5 readily inserts CO yielding the highly reactive acetyl derivative [Ni(COCH3)(‘S2C’)]−. This complex could not be isolated, but its formation was established

  一系列的[M（L）（ 'S 2 C'）]配合物（M =镍II，钯II，铂II），其含有碳烯二硫醇配体作者：2 C' 2- = 1,3- imidazolidinyl- N，已经合成了N′-双（2-苯硫基醚）（2-）和各种C和S共配体。当用KCN处理，Ñ -butylisonitrile，富电子烯烃- [R 2 C = CR 2 [=双（1,3- diphenylimidazolidine -2-亚基）]，石灰，硫醇盐如设置-，SPh上-或ö -SC 6 H 4 NH 2和硫化氢，母体配合物[Ni（'S 2 C'）] 2 ·DMF（1）得到相应的阴离子或中性[Ni（L）（'S 2 C'）]配合物，其分离为[K 2（Kryptofix5）（THF）2（μ-OH 2）] [镍（CN）（作者：2 C'）]（2），[镍（CNBu）（ 'S 2 C'）]（3），[ Ni（CR 2）（'S 2 C'）]
• Kristallstrukturen der Komplexe Von Quecksilber(Ii)Iodid und -Thiocyanat mit L,13-Bis(8-Chinolyl)-L,4,7,10,13-Pentaoxatridecan („Kryptand 5“)
  作者：Joachim Pickardt、Sven Wiese

  DOI：10.1515/znb-2000-1014

  日期：2000.10.1

  Reactions of 1,13-bis(8-chinolyl)-1,4,7,10,13-pentaoxatridecane (“Cryptand 5”) with HgX₂ (X = I, SCN) yield crystals of [(cryptand 5)(HgI₂)₂] (1) and [(cryptand 5 )₂Hg(SCN)₂}₄] (2), resp. In both complexes two molecules of HgX₂ are bound to one ligand molecule. 1 has symmetry C_i with the oxygen atom O(3 ) of the ether chain on a center of symmetry of the unit cell, each Hg atom is bound to the two I atoms, the N atom of the chinolyl residue, and one oxygen atom, O(1) and O(l)ⁱ, resp. of the ligand; neighbouring complex units are connected via iodine bridges thus forming chains. In 2 also two formula units of HgX₂ are bound to one ligand molecule, but contrary to 1 the complex is not centrosymmetric. The Hg atoms of the two Hg(SCN)₂ groups are co-ordinated differently: both are bound via sulphur atoms to two SCN-groups, one being a terminal SCN group, the other acting as a bridge to the Hg atom of a neighbouring complex unit. The first Hg atom is connected to a chinolyl N atom and too oxygen atoms, the second to a chinolyl N atom and three oxygen atoms. There are two independent complex units per asymmetric unit which are related by a non-crystallographic twofold axis, and which are connected via two SCN bridges. These “double molecules” are also interconnected by thiocyanate bridges, thus forming a chain structure

  标题：摘要

  1,13-双(8-喹啉基)-1,4,7,10,13-五氧杂十三烷（“Cryptand 5”）与HgX₂（X = I，SCN）的反应产生了[(cryptand 5)(HgI₂)₂]（1）和[(cryptand 5)₂Hg(SCN)₂}₄]（2）的晶体。在这两种配合物中，两个分子的HgX₂与一个配体分子结合。1具有C_i对称性，醚链的氧原子O(3)位于晶胞的对称中心，每个Hg原子与两个I原子、喹啉基残基的N原子以及配体的一个氧原子O(1)和O(l)ⁱ结合。相邻的配合物单元通过碘桥连接形成链。在2中，同样有两个HgX₂的配方单位与一个配体分子结合，但与1不同，该配合物不对称。两个Hg(SCN)₂基团的Hg原子的配位方式不同：两者均通过硫原子与两个SCN基团结合，一个是末端的SCN基团，另一个作为桥连接到相邻复合物单元的Hg原子。第一个Hg原子连接到一个喹啉基N原子和两个氧原子，第二个连接到一个喹啉基N原子和三个氧原子。每个不对称单元有两个独立的复合物单元，它们通过非晶体学二倍轴相关，并通过两个SCN桥连接。这些“双分子”也通过硫氰酸盐桥连接在一起，形成链状结构。

• Surprisingly stable ammonium ion complex of a non-cyclic crown-type polyether: solid and solution studies
  作者：Ki-Min Park、Hyun Jee Kim、Suk-Hee Moon、Jagadese J. Vittal、Jong Hwa Jung、Shim Sung Lee

  DOI：10.1039/c0nj00074d

  日期：——

  The first crystal structure of an NH4+ ion complex with 1,13-bis(8-quinolyl)-1,4,7,10,13-pentaoxatridecane (L), a representative non-cyclic analogue of 18-crown-6, is reported along with the characteristics of the complex’s solution; very interestingly, L forms a more stable complex with the NH4+ ion than does 18-crown-6 by the formation of unique recognition tetrahedral-type hydrogen bonds.

  NH 4 +离子配合物的第一晶体结构1,13-双（8-喹啉基）-1,4,7,10,13-五氧杂癸（L），是...的代表性非循环类似物18冠6连同复杂解决方案的特征一起报告；非常有趣的是，与NH 4 +离子相比，L与NH 4 +离子形成更稳定的络合物18冠6 通过形成独特的识别四面体型 氢 债券。
• Synthesis, Structural Characterization, and Physical Properties of Alkylammonium Derivative Complex with Acyclic Crown Ether Analog
  作者：Eun-Ji Lee、Suk-Hee Moon、Shim-Sung Lee、Ki-Min Park

  DOI：10.5012/bkcs.2011.32.6.2097

  日期：2011.6.20

  The complexation abilities of cyclic or acyclic crown-type polyethers toward metal cations, ammonium (or alkylammonium) ion, and neutral molecules have attracted much attention during the last four decades because of their contributions to stereoselective complexation, cation transport, and enzyme chemistry. It is well-known that the cyclic polyethers such as 18-crown-6 show the excellent complexing

  环状或非环状冠型聚醚对金属阳离子、铵（或烷基铵）离子和中性分子的络合能力在过去 40 年中因其对立体选择性络合、阳离子传输和酶化学的贡献而备受关注。众所周知，18-crown-6等环状聚醚对带电荷或不带电荷的客体物种均表现出优异的络合能力和选择性。另一方面，无环聚醚的络合能力较弱，因为它们的构象自由度和络合过程效率低得多。然而，当二足型无环聚醚在低聚（乙二醇）骨架的两端具有刚性芳香族供体端基时，它们的络合能力显着提高。其中，1,13-bis-(8-quinolyl)-1,4,7,10,13-pentaoxatridecane (L) 是具有代表性的，并且因其对多种阳离子或中性客体的络合能力而被广泛研究，因为 L 具有以类似于 18-crown-6 的方式与客体形成伪环状配合物的吸引特征。然而，关于 L 和客体物种，特别是有机客体之间络合的晶体结构仍然很少见。