1,1'-<1,3-Propanediylbis(oxy)bis><4-(bromomethyl)benzene> | 477761-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1'-<1,3-Propanediylbis(oxy)bis><4-(bromomethyl)benzene>
• 英文别名: 1,3-bis-(4-bromomethyl-phenoxy)-propane；1,3-Bis-(4-brommethyl-phenoxy)-propan；1-(Bromomethyl)-4-[3-[4-(bromomethyl)phenoxy]propoxy]benzene
• CAS: 477761-64-1
• 化学式: C₁₇H₁₈Br₂O₂
• 分子量: 414.137
• InChiKey: WROQRCUWXZULKY-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C(Solv: acetone (67-64-1))
• 沸点：
  476.9±35.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1'-<1,3-Propanediylbis(oxy)bis><4-(bromomethyl)benzene> 在 palladium diacetate 、 甲酸:三乙胺 1:1 、 potassium carbonate 、 三苯基膦 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 9.0h， 生成 3,3'-<1,3-Propanediylbis(oxy-4,1-phenylenemethyleneoxy)>bis<2-hydroxybenzaldehyde>
  参考文献：
  名称：

  Molecular recognition of neutral molecules by metalloclefts: synthesis, x-ray structure, proton NMR spectroscopy, electrochemistry, and molecular modeling

  摘要：

  Metalloclefts 2 and 10a-b and metallomacrocycles 7a-c possessing a Lewis acidic uranyl cation were synthesized from the corresponding aldehydes. The complexation of these compounds with neutral molecules was assessed by H-1 NMR spectroscopy, X-ray structure determination, polarography, and molecular modelling. H-1 NMR titration experiments and the crystal structure of 10b.4-tert-butylpyridine indicate that the neutral guests coordinate with their Lewis basic site at the uranyl, and that pi-pi stacking of the aromatic rings of host and guest stabilizes the complexes. Free energies of complexation, for a series of hosts and guests, obtained from polarographic titration data, vary from 1.5 to greater-than-or-equal-to 6.3 kcal mol-1. Compared to the reference salophene-uranyl 11 the stabilities of the complexes are enhanced up to 1.7 kcal mol-1 for 2 and up to 1.6 kcal mol-1 for 10a-b; for the more rigid metallomacrocyles 7 increases up to 2.2 kcal mol-1 were found. The calculated and experimentally determined relative energies of complexation of 4-methylpyridine vs pyridine with 2, 10a-b, and 11 correspond quantitatively.

  DOI：

  10.1021/jo00007a023
• 作为产物：
  描述：

  对羟基苯甲醇 在 氢溴酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 1,1'-<1,3-Propanediylbis(oxy)bis><4-(bromomethyl)benzene>
  参考文献：
  名称：

  Analysis and Improvement of an Anion-Templated Rotaxane Synthesis

  摘要：

  A series of new rotaxanes with axles different in length was prepared. Following the synthetic protocol utilizing a known anion template effect (Scheme 1), surprisingly low yields in the order of 2 - 5% were obtained (Scheme 3), which furthermore significantly depended on the nature of the stopper (Fig. 1). Variations in the synthetic procedures and computational results from Monte Carlo simulations allowed us to analyze the origin of these findings: The rotaxane wheel 3 acts as a noncovalently bound 'protecting group' for the stopper nucleophile. The protection of the nucleophilic phenolate O-atom depends much on the steric demands of the stoppers (see 2 vs. 10) which induce different conformations of the wheel. Based on this model. an improved synthetic scheme is suggested.

  DOI：

  10.1002/1522-2675(200206)85:6<1578::aid-hlca1578>3.0.co;2-l

文献信息

• Synthesis and characterization of binuclear Zn(II)–cyclen complexes bridged by α,ω-bis(4-methylphenoxy) alkanes
  作者：Fuxian Wan、Changcheng Li、Lin Jiang、Ying Li

  DOI：10.1007/s11164-012-0528-7

  日期：2012.10

  A series of novel α,ω-bis(4-methylphenoxy) alkane functionalized cyclen ligands were synthesized by the nucleophilic substitution reaction of 1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane and α,ω-bis(4-bromomethylphenoxy) alkanes. The corresponding dimeric Zn(II)–cyclen complexes were obtained by reaction of these ligands with Zn(ClO4)2·6H2O. Ligands and complexes were characterized by FT-IR, 1H NMR, and elemental analysis.

  通过 1,4,7-三(叔丁氧羰基)-1,4,7,10-四氮杂环十二烷和α,ω-双(4-溴甲基苯氧基)烷烃的亲核取代反应，合成了一系列新型α,ω-双(4-甲基苯氧基)烷烃官能化环烯配体。通过这些配体与 Zn(ClO4)2-6H2O 反应，得到了相应的二聚 Zn(II)- 环烯配合物。配体和配合物通过傅立叶变换红外光谱、1H 核磁共振和元素分析进行了表征。
• Kyi, Huaxue Xuebao/Acta Chimica Sinica, 1959, vol. 25, p. 100,102
  作者：Kyi

  DOI：——

  日期：——