1,3,5-三(4'-羟基-2'-氧杂-1'-丁基)苯三(2'-四氢吡喃基)醚 | 152065-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3,5-三(4'-羟基-2'-氧杂-1'-丁基)苯三(2'-四氢吡喃基)醚
• 英文名称: 1,3,5-tris(4'-hydroxy-2'-oxa-1'-butyl)benzene tri(2'-tetrahydropyranyl) ether
• 英文别名: 1,3,5-tris-(2'-(2''-tetrahydropyranyloxy)ethoxymethyl)benzene；2-[2-[[3,5-Bis[2-(oxan-2-yloxy)ethoxymethyl]phenyl]methoxy]ethoxy]oxane
• CAS: 152065-57-1
• 化学式: C₃₀H₄₈O₉
• 分子量: 552.706
• InChiKey: XFUNDIODLDFIDF-UHFFFAOYSA-N

物化性质

• 沸点：
  650.6±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,5-三(4'-羟基-2'-氧杂-1'-丁基)苯三(2'-四氢吡喃基)醚 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,3,5-tris[4'-(tosyloxy)-2'-oxa-1'-butyl]benzene
  参考文献：
  名称：

  Novel benzene-bridged macrobi- and macrotricyclic polyethers

  摘要：

  Novel three-dimensional benzene-bridged macrobicyclic polyether 1 and macrotricyclic polyether 2 have been prepared. Macrobicyclic triply bridged cyclophane crown compound 1 was synthesized by a tripode-tripode coupling of 1,3,5-tris[7'-(tosyloxy)-2',5'-dioxa-1'-heptyl]benzene (19) with 1,3,5-tris(hydroxymethyl)benzene (5). Macrotricyclic quadruply bridged cyclophane crown ether 2 was obtained by a quadrupode-quadrupode coupling of 1,2,4,5-tetrakis(7'-tosyloxy-2,5'-dioxa-1'-heptyl)benzene (20) with 1,2,4,5-tetrakis(hydroxymethyl)benzene (6). These ligands could have suitable rigidity and cavity sizes for the coordination of metal cations. They appear to have selectivities for cesium over sodium and lead ions, and 2 shows a log K value of 3.50 for interaction with cesium ion in 80% CH3OH/20% water (v/v). Macrotricyclic polyether 2 containing benzene bridgeheads is a new type of ligand, and its structure was confirmed by an X-ray crystallographic study.

  DOI：

  10.1021/jo00079a013
• 作为产物：
  描述：

  均苯三甲酸 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 168.0h， 生成 1,3,5-三(4'-羟基-2'-氧杂-1'-丁基)苯三(2'-四氢吡喃基)醚
  参考文献：
  名称：

  具有e，e，e加成模式的[60]富勒烯三加合物的区域选择性合成和区域选择性脱保护。

  摘要：

  D（3h）对称的三脚架三（丙二酸酯）系链已用于合成[60]富勒烯三加合物，其e，e，e加成图带有拓扑上不同的极性和赤道加成区，可以选择性地脱保护。

  DOI：

  10.1039/b504748j

文献信息

• Synthesis and Orthogonal Functionalization of [60]Fullerene<i>e</i>,<i>e</i>,<i>e-</i>Trisadducts with Two Spherically Defined Addend Zones
  作者：Florian Beuerle、Andreas Hirsch

  DOI：10.1002/chem.200900329

  日期：2009.7.27

  of 13–15. As a consequence of the template‐directed synthesis, all e,e,e‐trisadducts were formed as in/out isomers exclusively and contain two spherically well‐defined addend zones with equatorial and polar orientation, respectively. By variation of the outer malonate termini of the tethers, selective functionalization of the equatorial addend zone could be achieved, thus leading to fine‐tuning of intermolecular

  e，e，e-三加合物13和15是通过三脚架丙二酸酯10和12与C 60的高度区域选择性三重环丙烷化反应制得的。产率和区域选择性取决于丙二单元连接到的焦点苯芯系绳的长度和结构13 - 15。模板定向合成的结果是，所有e，e，e三价合物都按进/出形式形成异构体，并且分别包含两个球形的定义明确的加合物区域，分别具有赤道和极性方向。通过改变系绳的外部丙二酸末端，可以实现赤道附加区的选择性功能化，从而导致分子间相互作用（如溶解度或聚集现象）的微调。在去除了14和15中的焦点苯部分后，可以实现极性附加区的选择性官能化。通过1 H NMR光谱分析可以观察到极性加成区中极性取代基的强大分子内氢键网络。通过两个加成区的正交官能化，富勒烯衍生物44 – 48可以作为一个单一的进/出异构体进行合成，从而大大增强了e，e，e- trisadducts作为超分子体系结构的基础。
• Method of synthesis of water soluble fullerene polyacids using a malonate reactant
  申请人：Hirsch Andreas

  公开号：US20060047167A1

  公开（公告）日：2006-03-02

  In one embodiment, the present invention is directed to a method for synthesizing compounds of the formula where C m is a fullerene having m carbon atoms, the method comprising the steps of forming a linear malonate compound of the formula where each Z is the same or different and is a straight-chain or branched-chain aliphatic radical having from 1-30 carbon atoms which may be unsubstituted or monosubstituted or polysubstituted by identical or different substitutents, in which radicals up to every third —CH 2 — unit can be replaced by O or NR″, n is an integer from 2 to 10, and the unfilled valences of the first and nth malonate groups are filled with bonds to hydrogen, a hydrocarbon group or substituted hydrocarbon group having 1-20 carbon atoms, or a chain containing unsubstituted or substituted aryl or other cyclic groups; or (ii) a branched malonate compound of the formula where Z′ is an aliphatic radical having from 1-30 carbon atoms which may be unsubstituted or monosubstituted or polysubstituted by identical or different substitutents, in which radicals up to every third —CH 2 — unit can be replaced by O or NR″; and n is an integer from 2 to 10; reacting said malonate compound with C m to form an adduct of the formula each Z is bonded to both one carboxylate group of a first malonate moiety and one carboxylate group of a second malonate moiety and the unfilled valences of the first and nth malonate groups are filled with bonds to hydrogen, a hydrocarbon group or substituted hydrocarbon group having 1-20 carbon atoms, or a chain containing unsubstituted or substituted aryl or other cyclic groups; and hydrolyzing said adduct to form the compound.

  在一个实施例中，本发明涉及一种合成具有下式的化合物的方法：其中Cm是具有m个碳原子的富勒烯，所述方法包括以下步骤：形成具有下式的线性马隆酸酯化合物：其中每个Z相同或不同，是具有1-30个碳原子的直链或支链脂肪族基，可以是未取代的或单取代的或多取代的相同或不同取代基取代的，其中每隔三个-CH2-单位的基可以被O或NR″替换，n是2到10的整数，第一个和第n个马隆酸酯基的未填充价键通过与氢、具有1-20个碳原子的烃基或取代烃基，或含有未取代或取代芳基或其他环状基团的链相连；或(ii)形成具有下式的支链马隆酸酯化合物：其中Z′是具有1-30个碳原子的直链或支链脂肪族基，可以是未取代的或单取代的或多取代的相同或不同取代基取代的，其中每隔三个-CH2-单位的基可以被O或NR″替换；n是2到10的整数；将所述马隆酸酯化合物与Cm反应，形成具有下式的加合物：其中每个Z连接到第一个马隆酸酯基和第二个马隆酸酯基的一个羧酸基，第一个和第n个马隆酸酯基的未填充价键通过与氢、具有1-20个碳原子的烃基或取代烃基，或含有未取代或取代芳基或其他环状基团的链相连；并水解所述加合物以形成所述化合物。
• Regioselective synthesis and zone selective deprotection of [60]fullerene tris-adducts with an e,e,e addition pattern
  作者：Florian Beuerle、Nikos Chronakis、Andreas Hirsch

  DOI：10.1039/b504748j

  日期：——

  D(3h)-symmetrical tripodal tris(malonate) tethers have been used for the synthesis of [60]fullerene tris-adducts with an e,e,e addition pattern bearing topologically distinct polar and equatorial addend zones that can selectively be deprotected.

  D（3h）对称的三脚架三（丙二酸酯）系链已用于合成[60]富勒烯三加合物，其e，e，e加成图带有拓扑上不同的极性和赤道加成区，可以选择性地脱保护。
• Novel benzene-bridged macrobi- and macrotricyclic polyethers
  作者：Haoyun An、Jerald S. Bradshaw、Krzysztof E. Krakowiak、Bryon J. Tarbet、N. Kent Dalley、Xiaolan Kou、Chengyue Zhu、Reed M. Izatt

  DOI：10.1021/jo00079a013

  日期：1993.12

  Novel three-dimensional benzene-bridged macrobicyclic polyether 1 and macrotricyclic polyether 2 have been prepared. Macrobicyclic triply bridged cyclophane crown compound 1 was synthesized by a tripode-tripode coupling of 1,3,5-tris[7'-(tosyloxy)-2',5'-dioxa-1'-heptyl]benzene (19) with 1,3,5-tris(hydroxymethyl)benzene (5). Macrotricyclic quadruply bridged cyclophane crown ether 2 was obtained by a quadrupode-quadrupode coupling of 1,2,4,5-tetrakis(7'-tosyloxy-2,5'-dioxa-1'-heptyl)benzene (20) with 1,2,4,5-tetrakis(hydroxymethyl)benzene (6). These ligands could have suitable rigidity and cavity sizes for the coordination of metal cations. They appear to have selectivities for cesium over sodium and lead ions, and 2 shows a log K value of 3.50 for interaction with cesium ion in 80% CH3OH/20% water (v/v). Macrotricyclic polyether 2 containing benzene bridgeheads is a new type of ligand, and its structure was confirmed by an X-ray crystallographic study.