1,3-bis(2-hydroxyphenoxy)propane | 42397-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-bis(2-hydroxyphenoxy)propane
• 英文别名: 1,3-bis(2’-hydroxyphenoxy)propane；1,3-bis-(2-hydroxyphenoxy)-propane；1,3-bis(o-hydroxyphenoxy)propane；1,3-(o-hydroxyphenoxy)propane；2,2'-propanediyldioxy-di-phenol；Trimethylenglykol-bis-(2-oxy-phenylaether)；Phenol, 2,2'-[1,3-propanediylbis(oxy)]bis-；2-[3-(2-hydroxyphenoxy)propoxy]phenol
• CAS: 42397-72-8
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: PKEYDCTUOCBKRP-UHFFFAOYSA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  426.4±25.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(2-hydroxyphenoxy)propane 在 lithium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 sym-dibenzo-14-crown-4-oxyacetic acid
  参考文献：
  名称：

  Crystal and molecular structure of the complex between sym-dibenzo-14-crown-4-oxyacetate and lithium(1+) ion, [C20H21O7]-.cntdot.Li+.cntdot.7.5H2O

  摘要：

  DOI：

  10.1021/ja00317a018
• 作为产物：
  描述：

  2-苯甲氧基苯酚 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 75.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 1,3-bis(2-hydroxyphenoxy)propane
  参考文献：
  名称：

  β1选择性肾上腺素受体拮抗剂。1.一系列二元（芳氧基）丙醇胺的合成和β-肾上腺素阻断活性。

  摘要：

  已经制备了一系列二元（芳氧基）丙醇胺，并在体内和体外检查了β-肾上腺素受体阻断活性。这些对称化合物由两个（S）-（苯氧基）丙醇胺药效基团组成，它们通过不同长度的亚烷基二氧基或聚（氧乙烯二氧基）连接单元偶联。已经制备了通过药效基团的芳环中的2,2'，3,3'和4,4'位置连接的这种二元化合物的实例。体外和体内试验数据表明，2,2'化合物倾向于是选择性的β2-肾上腺素能阻断剂，4,4'二元化合物倾向于是选择性的β-1肾上腺素阻断剂，而那些具有3,3'的化合物连接表现出中间选择性。4,4'-连接的二元化合物之一4s在体内表现出有效的心脏选择性β受体阻滞作用，

  DOI：

  10.1021/jm00365a004

文献信息

• Polybenzocrown ethers: synthesis by cesium-assisted cyclization and solid-state structures
  作者：Robert E. Hanes、Edward C. Ellingsworth、Scott T. Griffin、Robin D. Rogers、Richard A. Bartsch

  DOI：10.3998/ark.5550190.0011.717

  日期：——

  A series of large-ring polybenzocrown ethers is prepared by cesium-assisted cyclizations. Reactions of diphenols/bisphenols, dimesylates of oligoethylene glycols and cesium carbonate in MeCN produce the large-ring polybenzocrown ethers in high yields. To gain further insight into the structures of these compounds, solid-state structures of three large-ring crown ethers are obtained by X-ray diffraction

  通过铯辅助环化反应制备了一系列大环聚苯并冠醚。二酚/双酚、低聚乙二醇的二甲磺酸盐和碳酸铯在 MeCN 中的反应以高产率产生大环聚苯并冠醚。为了进一步了解这些化合物的结构，通过 X 射线衍射获得了三个大环冠醚的固态结构。
• Preparation of benzo- and polybenzocrown ethers by macrocyclization reactions
  作者：Robert E. Hanes、Jong Chan Lee、Sheryl N. Ivy、Anna Palka、Richard A. Bartsch

  DOI：10.3998/ark.5550190.0011.718

  日期：——

  the method was used for the preparation of monobenzocrown ethers. Interestingly, for the preparation of monobenzocrown ethers, [2+2] adducts were discovered to be significantly contaminating the products. Dimesylates were chosen as the leaving group due to their ease or preparation and the ability to use the unpurified products with no apparent impact on the macrocyclization.

  探索了冠醚的大环化及其制备方法。我们提出了一种稳健、可扩展的方法来制备这些大环。此外，研究了改变前体结构的影响，以确定双酚和二甲磺酸酯的“切割”是否影响反应过程，如通过产率测量的。此外，使用儿茶酚衍生物，该方法用于制备单苯并冠醚。有趣的是，在制备单苯并冠醚时，发现 [2+2] 加合物严重污染了产品。选择二甲磺酸盐作为离去基团是因为它们易于制备，并且能够使用未纯化的产物而对大环化没有明显影响。
• Synthesis of new lipophilic acyclic di-ionizable polyethers, bis(crown ethers) and macrocyclic diamides
  作者：Sadik Elshani、Chien M. Wai、N.R. Natale、Richard A. Bartsch

  DOI：10.1016/s0040-4020(99)00514-1

  日期：1999.7

  A series of new lipophilic acyclic polyethers containing two carboxylic or hydroxamic acid groups have been prepared. From lipophilic acyclic polyether dicarboxylic acids 2, 9 and 13, the bis(crown ethers) 20–25 were synthesized. From lipophilic acyclic polyether dicarboxylic acids 10–12 and 14, the new macrocyclic diamides 26–32 were prepared in high yields without the use of high dilution techniques

  已经制备了一系列含有两个羧酸或异羟肟酸基团的新的亲脂性无环聚醚。从亲脂性的非环状聚醚的二羧酸2,9和13中，双（冠醚）20-25被合成。由亲脂性无环聚醚二羧酸10-12和14可以高收率制备新的大环二酰胺26-32，而无需使用高稀释技术或模板效果。
• Microwave-Assisted Synthesis of Dibenzo-Crown Ethers
  作者：Rey Torrejos、Grace Nisola、Arnel Beltran、Myoung Park、Basavaraj Patil、Seong-Poong Lee、Jeong Seo、Wook-Jin Chung

  DOI：10.2174/15701786113106660075

  日期：2014.1.31

  Microwave-assisted organic synthesis (MAOS) for dibenzo-substituted crown ethers is presented. Two routes were developed: (1) one-pot MAOS for symmetric dibenzo-crown ethers (DBC) and (2) a two-step MAOS via diphenol intermediates for both symmetric and asymmetric DBCs. MAOS were carried out in open or closed vessels, with or without temperature control at various microwave settings using different bases and reactants. Open vessel MAOS was limited by the volatility of reactants hence was less preferred than the closed vessel MAOS. DBC formation was highly affected by the cation size of the base, which acted as a template ion during DBCs ring closure. Closed vessel MAOS without temperature control was found most appropriate for DBC synthesis. Symmetric DBCs were conveniently obtained via one-pot MAOS whereas asymmetric DBCs were obtained from two-step MAOS via diphenol intermediates. The method was found expedient as it afforded satisfactory yields at considerably shorter reaction time than those in conventional methods.

  本文介绍了二苯并取代冠醚的微波辅助有机合成（MAOS）。该研究开发了两种路线：(1) 一锅 MAOS，用于对称二苯并皇冠醚 (DBC)；(2) 两步 MAOS，通过二苯酚中间体，用于对称和不对称二苯并皇冠醚。MAOS 在开放式或封闭式容器中进行，使用不同的碱和反应物，在不同的微波设置下进行温度控制或不进行温度控制。开式容器 MAOS 受反应物挥发性的限制，因此不如闭式容器 MAOS 更受青睐。DBC 的形成受碱阳离子大小的影响很大，碱阳离子在 DBC 闭环过程中起着模板离子的作用。无温度控制的密闭容器 MAOS 最适合用于合成 DBC。通过一锅 MAOS 法可以方便地获得对称的二溴环十二烷，而通过二苯酚中间体的两步 MAOS 法则可以获得不对称的二溴环十二烷。与传统方法相比，该方法方便快捷，反应时间大大缩短，产量令人满意。
• 다중벽 탄소나노튜브 지지체에 고정시킨 크라운 에테르, 그 제조방법 및 그 용도
  申请人：Myongji University Industry and Academia Cooperation Foundation 명지대학교 산학협력단(220050139720) BRN ▼135-82-11060

  公开号：KR20160088227A

  公开（公告）日：2016-07-25

  본 발명은 다중벽 탄소나노튜브 지지체에 고정시킨 크라운 에테르, 그 제조방법 및 그 용도에 관한 것으로, 더욱 상세하게는 크라운 에테르를 다중벽 탄소나노튜브 지지체에 고정시킴으로써 리튬이온 흡착 성능을 현저하게 개선시킬 수 있는 크라운 에테르, 그 제조방법 및 그 용도에 관한 것이다. 구체적으로 상기 제조방법은 하이드록시-다이벤조-14-크라운-4 에테르(Hydroxy-Dibenzo-14-Crown-4 ether)를 다중벽 탄소나노튜브(multi-walled carbon nanotube)에 고정시키는 방법으로 수행될 수 있다. 상기 방법에 따라 제조된 크라운 에테르는 유용한 금속 이온(리튬 이온)을 회수하는데 이용될 수 있다.

  这项发明涉及固定在多壁碳纳米管支撑体上的冠醚，其制备方法及其用途，更详细地说，涉及通过将冠醚固定在多壁碳纳米管支撑体上，从而显着改善锂离子吸附性能的冠醚，其制备方法及其用途。具体而言，上述制备方法可以通过将羟基-二苯并-14-冠-4醚（Hydroxy-Dibenzo-14-Crown-4 ether）固定在多壁碳纳米管（multi-walled carbon nanotube）上来实现。通过该方法制备的冠醚可用于回收有用的金属离子（锂离子）。