1,2-bis(2-ethoxyphenol)ethane | 68380-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-bis(2-ethoxyphenol)ethane
• 英文别名: 1,2-bis[2-(2-hydroxyethoxy)phenoxy]ethane；2-[2-[2-[2-(2-hydroxyethoxy)phenoxy]ethoxy]phenoxy]ethanol
• CAS: 68380-65-4
• 化学式: C₁₈H₂₂O₆
• 分子量: 334.369
• InChiKey: DRLQVPWYGDZWRT-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  522.1±45.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis(2-ethoxyphenol)ethane 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Macroring-neutral molecule complexation. Synthesis of biconcave pyridino hosts, complex formation, and x-ray crystal structures of two inclusion compounds

  摘要：

  A series of pyridino macrocycles 1-3(a-e) incorporating rigid bi- and triaryl ether segments in different ring positions have been synthesized. The effect of incorporation of these building blocks into a given macroring framework on the host properties for uncharged-molecule inclusion has been studied. Symmetric 21-membered macrorings 1c, 1d, or 2c, 2d with tri-o-phenylene, tri-2,3-naphthylene, or mixed phenylene naphthylene ether units are efficient hosts in solid-state complexation of dipolar-aprotic and apolar guests such as nitro compounds and nitriles as well as DMF, DMSO, THF, dioxane, or benzene. X-ray analyses of the solid-state complexes of 1d with PhNO2 (1:1) and MeCN (1:1) have been studied. It is shown that the presence of the triaryl ether segment induces a biconcave nonequally sided host conformation suitable for guest inclusion. The packing characterizes the host-guest topologies of the two inclusion compounds to be of (H-bonded) cavitate-type for the MeCN case and of interstitial channel type for the PhNO2 case. A comparative discussion of the present and previous results support the interpretation of hemispherand preorganization for the new host structures.

  DOI：

  10.1021/jo00003a055
• 作为产物：
  描述：

  2,2'-<1,2-Ethandiyloxybis(oxy-2,1-phenylenoxy)>bisethanol-dibenzylether 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、303.97 kPa 条件下， 反应 4.0h， 以85%的产率得到1,2-bis(2-ethoxyphenol)ethane
  参考文献：
  名称：

  Macroring-neutral molecule complexation. Synthesis of biconcave pyridino hosts, complex formation, and x-ray crystal structures of two inclusion compounds

  摘要：

  A series of pyridino macrocycles 1-3(a-e) incorporating rigid bi- and triaryl ether segments in different ring positions have been synthesized. The effect of incorporation of these building blocks into a given macroring framework on the host properties for uncharged-molecule inclusion has been studied. Symmetric 21-membered macrorings 1c, 1d, or 2c, 2d with tri-o-phenylene, tri-2,3-naphthylene, or mixed phenylene naphthylene ether units are efficient hosts in solid-state complexation of dipolar-aprotic and apolar guests such as nitro compounds and nitriles as well as DMF, DMSO, THF, dioxane, or benzene. X-ray analyses of the solid-state complexes of 1d with PhNO2 (1:1) and MeCN (1:1) have been studied. It is shown that the presence of the triaryl ether segment induces a biconcave nonequally sided host conformation suitable for guest inclusion. The packing characterizes the host-guest topologies of the two inclusion compounds to be of (H-bonded) cavitate-type for the MeCN case and of interstitial channel type for the PhNO2 case. A comparative discussion of the present and previous results support the interpretation of hemispherand preorganization for the new host structures.

  DOI：

  10.1021/jo00003a055

文献信息

• Calix[4]arene dibenzocrown ethers as caesium selective extractants
  作者：Jong Seung Kim、Jin Hyun Pang、Ill Yong Yu、Won Ku Lee、Il Hwan Suh、Jong Kuk Kim、Moon Hwan Cho、Eun Tae Kim、Do Young Ra

  DOI：10.1039/a808499h

  日期：——

  A series of 1,3-dialkyloxycalix[4]arene dibenzocrown ethers were synthesized in the fixed 1,3-alternate conformation with good yields by the reaction of 1,3-dialkyloxycalix[4]arenes with dibenzodimesylate in the presence of caesium carbonate. The three dimensional 1,3-alternate conformation was confirmed by X-ray crystal structure. Upon two phase extraction, NMR studies on the ligand–metal complex, single ion and competitive ion transport experiments through a bulk liquid membrane, 1,3-dipropyloxycalix[4]arene dibenzocrown-6, in which two benzo groups are symmetrically attached to the crown-6 linkage, gave one of the most efficient and selective extractabilities for caesium ion over other alkali metal ions. From supported liquid membrane experiments using 1 and 3 as organic carriers, permeation coefficients of the caesium ion were estimated to be 0.42 and 0.27 cm h–1, respectively. The selectivity of caesium over sodium ion was observed to increase with permeation time.

  在碳酸铯存在下，1,3-二烷氧基钙并[4]烯与二苯并二甲酸酯发生反应，合成了一系列具有固定 1,3 邻构象的 1,3 二烷氧基钙并[4]烯二苯并冠醚，并获得了良好的产率。X 射线晶体结构证实了这种三维 1,3 邻位构象。经过两相萃取、配体-金属复合物核磁共振研究、单离子和竞争性离子通过体液膜的传输实验，1,3-二丙基氧基钙[4]烯二苯并冠-6（其中两个苯并基团对称地连接到冠-6 连接上）对铯离子的萃取效率和选择性超过了其他碱金属离子。在使用 1 和 3 作为有机载体的支撑液膜实验中，铯离子的渗透系数估计分别为 0.42 和 0.27 cm h-1。据观察，铯对钠离子的选择性随着渗透时间的延长而增加。
• Studies on Synthetic Ionophores. VI. Synthesis of Polyether Carboxylic Acids and Their Use as Carriers for Alkali Metal Ion Transport through Liquid Membrane
  作者：Kazuo Yamaguchi、Shigeto Negi、Shohei Kozakai、Roichi Nagano、Hitoshi Kuboniwa、Akira Hirao、Seiichi Nakahama、Noboru Yamazaki

  DOI：10.1246/bcsj.61.2047

  日期：1988.6

  group of aromatic and tetrahydrofuran rings, number of ether oxygens, and terminal hydroxyl group of the ionophores on the ion transport ability and selectivity were investigated. The hydrophobic groups increased total amount of transported ions as well as partition coefficients. The ionophore, 5, which contains five ether oxygens, two aromatic rings, and o-toluic acid moiety transported K+ selectively

  ω-羟基羧酸（3, 5, 6, 7, 10, 12, 14, 17, 18, 20, and 22）带有 2-6 个醚氧和芳香环，带或不带四氢呋喃环，ω-甲氧基和合成了 5 (8 和 9) 的 ω-苄氧基衍生物。它们被用作碱金属离子通过液膜的主动和竞争性传输以及将碱金属离子提取到有机层的载体。研究了芳香环和四氢呋喃环的疏水基团、醚氧的数量和离子载体的末端羟基对离子传输能力和选择性的影响。疏水基团增加了传输离子的总量以及分配系数。离子载体，5，包含五个醚氧，两个芳环，和邻甲苯甲酸部分通过 1,2-二氯乙烷选择性地通过 Na+ 和 Li+ 传输 K+，与提取实验一致。间位和对位取代的异构体 6 和 7 没有表现出通过 1...
• Crown calix[4]arenes, method of preparation and use for selective
  申请人：Commissariat a l'Energie Atomique

  公开号：US06156282A1

  公开（公告）日：2000-12-05

  The invention relates to new calixarenes of formula: ##STR1## in which R.sup.1 represents a crown ether chain that includes at least two aryl or cycloalkyl rings, R.sup.2 is a hydroxyl or alkoxy group, or the two R.sup.2 groups together form a crown ether chain such as R.sup.1, and R.sup.3 represents a hydrogen atom or an alkyl group. The calixarenes are used to selectively extract caesium from aqueous solutions that notably have high concentrations of sodium.

  本发明涉及新的卡立克环化合物，其化学式为：##STR1## 其中R1代表至少包含两个芳基或环烷基环的冠醚链，R2为羟基或烷氧基，或两个R2共同形成类似R1的冠醚链，R3代表氢原子或烷基。这些卡立克环化合物用于从高浓度钠的水溶液中选择性地提取铯。
• A new calix[4]arene-bis(crown ether) derivative displaying an improved caesium over sodium selectivity: molecular dynamics and experimental investigation of alkali-metal ion complexation
  作者：Véronique Lamare、Jean-François Dozol、Saowarux Fuangswasdi、Françoise Arnaud-Neu、Pierre Thuéry、Martine Nierlich、Zouhair Asfari、Jacques Vicens

  DOI：10.1039/a806714g

  日期：——

  In the light of computational studies suggesting enhanced cation-binding abilities for various benzo derivatives of calix[4]arene-bis-crown-6 macrocycles, the synthesis and properties of one of these ligands, BC6B2, have been investigated. In this compound, di(1,2-phenylene)-annelated glycolic chains link the 1,3- and 2,4-phenyl rings of the calixarene, thereby forcing it into the 1,3-alternate conformation. The detailed structures of BC6B2·CH3NO2 1 and Cs2(NO3)2BC6B2·CHCl3·H2O 2 have been established by X-ray crystallography. Studies of coordination and solvent extraction of the alkali-metal ions have been used to compare this ligand with a number of related systems known previously.

  根据计算研究表明杯[4]芳烃-双冠-6大环的各种苯并衍生物的阳离子结合能力增强，对这些配体之一BC6B2的合成和性质进行了研究。在该化合物中，二(1,2-亚苯基)-稠合的乙醇链连接杯芳烃的1,3-和2,4-苯环，从而迫使其形成1,3-交替构象。通过X射线晶体学确定了BC6B2·CH3NO2 1 和Cs2(NO3)2BC6B2·CHCl3·H2O 2 的详细结构。碱金属离子的配位和溶剂萃取研究已用于将该配体与先前已知的许多相关系统进行比较。
• ION TRANSPORT ABILITY AND SELECTIVITY RELATING TO THE STRUCTURE OF SYNTHETIC IONOPHORES
  作者：Hitoshi Kuboniwa、Kazuo Yamaguchi、Akira Hirao、Seiichi Nakahama、Noboru Yamazaki

  DOI：10.1246/cl.1982.1937

  日期：1982.12.5

  bearing hydroxy group at the end and the methylether of 1 (4) were prepared. With active transport of Na+ and K+ by 1∼4, 1 and 4 exhibited K+-selectivity over Na+, while 2, and 3 had no transport ability. From the results of ion transport and 1H-NMR study, relationship between the structure and transport ability was discussed.

  制备了聚醚链末端带有羟基的邻、间、对位取代的苯甲酸 (1, 2, 3) 和 1 (4) 的甲基醚。Na+ 和 K+ 主动转运 1∼4，1 和 4 表现出对 Na+ 的 K+ 选择性，而 2 和 3 没有转运能力。从离子输运和1H-NMR研究的结果，讨论了结构与输运能力之间的关系。