[1,4-phenylene-bis(methyleneoxy-4,1-phenylene)]dimethanol | 170651-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [1,4-phenylene-bis(methyleneoxy-4,1-phenylene)]dimethanol
• 英文别名: [4-[[4-[[4-(Hydroxymethyl)phenoxy]methyl]phenyl]methoxy]phenyl]methanol
• CAS: 170651-96-4
• 化学式: C₂₂H₂₂O₄
• 分子量: 350.414
• InChiKey: DKPZOBLMYRAMRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  [1,4-phenylene-bis(methyleneoxy-4,1-phenylene)]dimethanol 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到1,4-Bis[[4-(chloromethyl)phenoxy]methyl]benzene
  参考文献：
  名称：

  Synthesis and Molecular Transformations of Functionalised Cyclophanes with Large Cavity

  摘要：

  Cyclophanes of the type 1 & 3 are obtained by the coupling of suitable dithiol with corresponding dibromide under high dilution technique in the presence of KOH in benzene or toluene-ethanol. Few molecular transformations have been effected on the cyclophanes 1 and 2.

  DOI：

  10.1080/00397919508011438
• 作为产物：
  描述：

  1,4-benzyloxy-bis(4-benzaldehyde) 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以85%的产率得到[1,4-phenylene-bis(methyleneoxy-4,1-phenylene)]dimethanol
  参考文献：
  名称：

  Dioxastilbenophanes—synthesis and charge transfer complexation studies

  摘要：

  Intramolecular McMurry coupling of dialdehydes derived from xylenyl dibromide and 4-hydroxy benzaldehyde afforded cis-stilbenophanes along with cyclophane diols. Stilbenophanes with a large cavity were also synthesized. Charge transfer complexations of the stilbenophanes with TCNE, TCNQ and PQT were studied. Some stilbenophanes form a relatively stronger complex with PQT rather than with TCNE and TCNQ. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.01.008

文献信息

• Is [N⁺−H···O] Hydrogen Bonding the Most Important Noncovalent Interaction in Macrocycle−Dibenzylammonium Ion Complexes?
  作者：Pin-Nan Cheng、Po-Yi Huang、Wan-Sheung Li、Shau-Hua Ueng、Wei-Chung Hung、Yi-Hung Liu、Chien-Chen Lai、Yu Wang、Shie-Ming Peng、Ito Chao、Sheng-Hsien Chiu

  DOI：10.1021/jo052411+

  日期：2006.3.1

  host molecule in which one diethylene glycol chain (i.e., a loop possessing only three oxygen atoms) incorporated along with two phenolic aromatic rings is linked by a xylene spacer into a macroring. The design of the molecular structure of this macrocycle “amplifies” any potential [cation···π], [N+−H···π], and [N+C−H···π] interactions between the dibenzylammonium (DBA+) ion and the phenolic rings of

  我们报告了一个新的宿主分子，其中一个二甘醇链（即，仅具有三个氧原子的环）与两个酚醛芳香环结合在一起，并通过二甲苯间隔基连接到一个大环上。该大环分子结构的设计“放大”了二苄基铵之间的任何可能的[阳离子···π]，[N + -H···π]和[N + CHH···π]相互作用（ DBA +）离子和大环的酚环；因此，这些物质在CD 3 NO 2中显示出非常强的结合亲和力（K a = 15000 M - 1）。该大环还以[2]假轮烷形式与双吡啶鎓离子配位，这使其成为已知的在溶液中络合DBA +和双吡啶鎓离子的最小的大环（即25元环）。为了明确确认溶液中存在这些假轮烷，我们合成了它们相应的互锁分子，即轮烷和链烷。
• Benzyl alcohol-based synthesis of mono- and bis-dihydropyridines in the presence of Al(HSO4)3, sodium nitrite, and sodium bromide under solvent-free conditions
  作者：L. Z. Fekri、M. Nikpassand

  DOI：10.1134/s1070363216060281

  日期：2016.6

  Dihydropyridines were synthesized in good to excellent yields in the presence of NaNO2, Al(HSO4)(3), and a catalytic amount of NaBr at room temperature. Low cost, the use of available reagents, simple methodology, and easy work-up procedure make this method attractive for organic synthesis.
• Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure
  作者：Arunachalam Kannan、Perumal Rajakumar、V. Kabaleeswaran、S. S. Rajan

  DOI：10.1021/jo950957y

  日期：1996.1.1

  Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-alpha,alpha'-dithiol (9), p-xylene-alpha,alpha'-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide Bb or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol as with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by H-1 NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex.
• A new macrocycle that forms pseudorotaxane-like complexes with dibenzylammonium ions
  作者：Pin-Nan Cheng、Wei-Chung Hung、Sheng-Hsien Chiu

  DOI：10.1016/j.tetlet.2005.04.063

  日期：2005.6

  A new host molecule in which only one diethylene glycol chain (i.e., a loop possessing only three oxygen atoms) suitably positioned in a macroring recognizes a DBA(+) ion to form a 1:1 pseudorotaxane-like complex. To confirm unambiguously that the pseudorotaxane exists in solution, a corresponding interlocked rotaxane molecule was synthesized. (c) 2005 Elsevier Ltd. All rights reserved.