1,13-bis[4-(hydroxymethyl)benzyl]-1,4,7,10,13-pentaoxatridecane | 175296-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,13-bis[4-(hydroxymethyl)benzyl]-1,4,7,10,13-pentaoxatridecane
• 英文别名: [4-[2-[2-[2-[2-[4-(Hydroxymethyl)phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]phenyl]methanol；[4-[2-[2-[2-[2-[4-(hydroxymethyl)phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]phenyl]methanol
• CAS: 175296-45-4
• 化学式: C₂₂H₃₀O₇
• 分子量: 406.476
• InChiKey: SCCVAQOWOOXELL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,13-bis[4-(hydroxymethyl)benzyl]-1,4,7,10,13-pentaoxatridecane 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 sodium hydroxide 、 二氯甲烷 、 乙腈 为溶剂， 生成 1,13-bis-(4-formylphenyl)-1,4,7,10,13-pentaoxatridecane
  参考文献：
  名称：

  Intramolecular Cannizzaro desymmetrization of tetraethylene glycol assisted by a cation binding template

  摘要：

  The synthesis of desymmetrized tetraethylene glycol possessing a benzyl alcohol and a benzoic acid end group via a Cannizzaro reaction is reported. The barium cation template used was found to be essential for a successful transformation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.093
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 对羟基苯甲醇 在 sodium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 4.0h， 以93%的产率得到1,13-bis[4-(hydroxymethyl)benzyl]-1,4,7,10,13-pentaoxatridecane
  参考文献：
  名称：

  Barium Cation Complexation by Flexible Mono- and Ditopic Receptors, Studied by UV Absorption and Fluorescence Spectroscopy

  摘要：

  The metal cation (Ba++) binding ability of a family of designed nonconjugated bichromophoric [bis(para-phenylene)or bis(para-diphenylene)]polyoxamacrocyclic coronands has been studied in acetonitrile in the ground state and in the singlet excited state. The association constants (K) at ambient temperature have been determined from UV absorption and fluorescence data, by use of the LETAGROP-SPEFO programme. The ground state complexes exhibit 1:1 or 1:1 and 2:1 (cation/ligand) stoichiometries and a large variety of association constants, as well as diverse cooperative effects. Remarkably, TTO5O5 {1,4,7,10,13,21,24,27,30,33-decaoxa-[13.15]-(1,4)benzenophane} shows a strong binding ability (log beta = 10.3) with a positive cooperativity. The apparent association constants measured from stationary fluorescence data were found to be lower in some cases than those observed in the ground state; these results strongly suggest that a transitory photodecomplexation between the metal cation and the phenolic oxygen atoms occurs in the S-1 state. An Xray structure analysis was performed on the barium complex of a related podand and the Ba++ coordination number was found to be 10.

  DOI：

  10.1002/1099-0690(20021)2002:2<331::aid-ejoc331>3.0.co;2-e

文献信息

• [2]Rotaxane Formation by Transition State Stabilization
  作者：Guillaume De Bo、Guillaume Dolphijn、Charlie T. McTernan、David A. Leigh

  DOI：10.1021/jacs.7b05640

  日期：2017.6.28

  We report on the synthesis of [2]rotaxanes driven by stabilization of the axle-forming transition state. A bifunctional macrocycle, with hydrogen bond donors at one end and acceptors at the other, is used to stabilize the charges that develop during the addition of a primary amine to a cyclic sulfate.

  我们报告了由形成轴的过渡态稳定驱动的 [2] 轮烷的合成。一个双功能大环，一端是氢键供体，另一端是受体，用于稳定伯胺加入环状硫酸盐过程中产生的电荷。