2,6-diiodo-4-(octyloxy)pyridine | 1032413-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-diiodo-4-(octyloxy)pyridine
• 英文别名: 2,6-Diiodo-4-octoxypyridine
• CAS: 1032413-20-9
• 化学式: C₁₃H₁₉I₂NO
• 分子量: 459.109
• InChiKey: TWSDHIQZEBVYMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-diiodo-4-(octyloxy)pyridine 在 正丁基锂 、 甲醇 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以54%的产率得到2-iodo-4-octyloxypyridine
  参考文献：
  名称：

  Synthesis of Strained Pyridine-Containing Cyclyne via Reductive Aromatization

  摘要：

  The Sonogashira-Hagihara coupling reactions of 2,6-diiodopyridine and cis-3,6-diethynyl-3,6-dimethoxycy-clohexa-1,4-diene or cis-9,10-diethynyl-9,10-dimethoxy-9, 10-dihydroanthracene gave macrocyclic compounds having alternating 2,6-diethynylpyridine and 3,6-dimethoxycyclohexa-1,4-diene segments. Transformation of the C(3)-symmetric 2,6-diethynylpyridine-based cyclo-trimer was efficiently achieved using tin-mediated reductive aromatization under mild conditions.

  DOI：

  10.1021/jo1006202
• 作为产物：
  描述：

  2,6-dibromo-4-octoxypyridine 在 copper(l) iodide 、 sodium iodide 作用下， 生成 2,6-diiodo-4-(octyloxy)pyridine
  参考文献：
  名称：

  Synthesis of Strained Pyridine-Containing Cyclyne via Reductive Aromatization

  摘要：

  The Sonogashira-Hagihara coupling reactions of 2,6-diiodopyridine and cis-3,6-diethynyl-3,6-dimethoxycy-clohexa-1,4-diene or cis-9,10-diethynyl-9,10-dimethoxy-9, 10-dihydroanthracene gave macrocyclic compounds having alternating 2,6-diethynylpyridine and 3,6-dimethoxycyclohexa-1,4-diene segments. Transformation of the C(3)-symmetric 2,6-diethynylpyridine-based cyclo-trimer was efficiently achieved using tin-mediated reductive aromatization under mild conditions.

  DOI：

  10.1021/jo1006202

文献信息

• Azacrown-attached meta-ethynylpyridine polymer: saccharide recognition regulated by supramolecular device
  作者：Hajime Abe、Shunsuke Takashima、Tsuyoshi Yamamoto、Masahiko Inouye

  DOI：10.1039/b902269d

  日期：——

  Polymeric synthetic host 2, azacrown-attached 2,6-pyridylene ethynylene polymer, was investigated for its saccharide recognition and the additive effect of triethylene tetramine–trifluoroacetic acid; heteroallosteric effects were observed on the basis of CD and UV/Vis analyses, which indicated saccharide-dependent stabilization and destabilization of helical complexes by the formation of pseudopolyrotaxanes.

  研究了聚合物合成宿主 2（偶氮冠连接的 2,6-吡啶乙炔聚合物）的糖识别能力和三乙烯四胺-三氟乙酸的添加效应；根据 CD 和 UV/Vis 分析，观察到了异质柱效应，这表明通过形成伪多原烷，螺旋复合物的稳定和不稳定取决于糖。
• <i>D</i>_3<i>h</i>-Symmetrical Shape-Persistent Macrocycles Consisting of Pyridine-Acetylene-Phenol Conjugates as an Efficient Host Architecture for Saccharide Recognition
  作者：Hajime Abe、Tetsuhiro Yoneda、Yuki Ohishi、Masahiko Inouye

  DOI：10.1002/chem.201603987

  日期：2016.12.23

  pyridine and three phenol rings linked with acetylene bonds were developed as a preorganized host for saccharide recognition by push–pull‐type hydrogen bonding. Three tert‐butyl or 2,4,6‐triisopropylphenyl substituents were introduced on the host to suppress self‐aggregation by steric hindrance. In spite of the simple architecture, association constants Ka of the host with alkyl glycoside guests reached

  由三个吡啶和三个与乙炔键连接的苯酚环组成的六边形持久大环化合物（SPM）被开发为通过推挽式氢键识别糖的预组织宿主。在主体上引入了三个叔丁基或2,4,6-三异丙基苯基取代基，以通过空间位阻抑制自聚集。尽管结构简单，但是主体与烷基糖苷客体的缔合常数K a达到10 6  m -1的数量级。根据UV / Vis滴定实验。由于氢键结合位点的预组织带来了熵的优势，因此这种糖苷的识别能力比无环等价宿主强得多。通过使用天然糖证明了固液萃取和液膜通过液膜的运输，并且观察到了对甘露糖的更多偏爱。
• Saccharide Recognition by a Three‐Arm‐Shaped Host Having Preorganized Three‐Dimensional Hydrogen‐Bonding Sites
  作者：Yuki Ohishi、Kentaro Masuda、Kazuki Kudo、Hajime Abe、Masahiko Inouye

  DOI：10.1002/chem.202004147

  日期：2021.1.7

  was readily prepared compared to a cage‐shaped analogue. This host associated with lipophilic glycosides to form chiral complexes, and the association constants were sufficiently high as to be comparable to those of the cage‐shaped analogue. Furthermore, this host extracted native monosaccharides into a lipophilic solvent.

  通常，由于三维预组织的氢键结合位点，糖的笼形宿主可以与客体分子牢固结合。然而，由于大环化步骤的产率低，通常很难制备笼状分子。在这里，我们报告一个具有吡啶-乙炔-苯酚单元的三臂形分子，作为一种具有预先组织的三维氢键位点的新型主体。与笼形类似物相比，这种三臂形宿主易于准备。该宿主与亲脂性糖苷结合形成手性复合物，缔合常数足够高，足以与笼形类似物的缔合常数相比。此外，该宿主将天然单糖提取到亲脂性溶剂中。
• Native Mannose‐Dominant Extraction by Pyridine–Phenol Alternating Oligomers Having an Extremely Efficient Repeating Motif of Hydrogen‐Bonding Acceptors and Donors
  作者：Yuki Ohishi、Hajime Abe、Masahiko Inouye

  DOI：10.1002/chem.201503149

  日期：2015.11.9

  saccharides. The longer oligomer strongly bound to lipophilic glycosides in 1,2‐dichloroethane, and association constants approached 108 M−1. Moreover, the oligomer extracted native saccharides from a solid phase to apolar organic solvents up to the extent of an equal amount of the oligomer and showed mannose‐dominant extraction among naturally abundant hexoses. The oligomer bound to native saccharides even

  设计并合成了吡啶-苯酚交替低聚物，其中吡啶和苯酚部分通过乙炔键在芳香环的2,6-位交替连接。吡啶氮原子和附近的酚羟基经过定向，因此它们不形成分子内氢键，而是以推挽方式协同作用作为糖的羟基的氢键受体和供体。较长的低聚物与1,2-二氯乙烷中的亲脂性糖苷牢固结合，缔合常数接近10 8  M -1。此外，低聚物从固相到非极性有机溶剂中提取天然糖的程度达到了等量的低聚物的程度，并显示出天然丰富的己糖中甘露糖占主导地位。即使在20％DMSO中的1,2-二氯乙烷中，低聚物也能与天然糖结合，并且对于D-甘露糖和D-葡萄糖显示出大于10 M -1的缔合常数 。
• A Pyridine‐Acetylene‐Aniline Oligomer: Saccharide Recognition and Influence of this Recognition Array on the Activity as Acylation Catalyst
  作者：Yuki Ohishi、Toshikazu Takata、Masahiko Inouye

  DOI：10.1002/cplu.202000603

  日期：2020.12

  of foldamer‐type hosts, various kinds of recognition arrays are expected to be developed. Here, a pyridine‐acetylene‐aniline unit is presented as a new class of a saccharide recognition array. The conformational stabilities of this array were analyzed by DFT calculation, and suggested that a pyridine‐acetylene‐aniline oligomer tends to form a helical structure. An oligomer of this array was synthesized

  为了创建折叠式主机的新功能，预计将开发各​​种识别阵列。在这里，吡啶-乙炔-苯胺单元被作为一种新型的糖类识别阵列。通过DFT计算分析了该阵列的构象稳定性，表明吡啶-乙炔-苯胺低聚物趋于形成螺旋结构。合成了该阵列的低聚物，并通过1 H NMR测量证实了其与辛基β -D-吡喃葡萄糖苷的缔合。UV / Vis，圆二色性和荧光滴定实验表明，它对非极性溶剂中的辛基糖苷具有很高的亲和力（K a = 10 4至10 5  M -1）。该低聚物在碱性条件下相对稳定，因此预期该阵列可用于糖的衍生化。一种由4-（二烷基氨基）吡啶连接的吡啶-乙炔-苯胺低聚物被证明催化辛基糖苷的酰化作用。