1,1'-bis<4-(bromomethyl)benzene> | 111285-03-1

• 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'-bis<4-(bromomethyl)benzene>
• 英文别名: 1-(Bromomethyl)-4-[2-[2-[4-(bromomethyl)phenoxy]ethoxy]ethoxy]benzene
• CAS: 111285-03-1
• 化学式: C₁₈H₂₀Br₂O₃
• 分子量: 444.163
• InChiKey: GRGBKCXOFISNLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1'-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'-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：

  4,4'-bis(benzenemethanol) 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到1,1'-bis<4-(bromomethyl)benzene>
  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

文献信息

• Ionene elastomers
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0228803B1

  公开（公告）日：1992-09-16
• US4677182A
  申请人：——

  公开号：US4677182A

  公开（公告）日：1987-06-30
• US4734458A
  申请人：——

  公开号：US4734458A

  公开（公告）日：1988-03-29
• US4794031A
  申请人：——

  公开号：US4794031A

  公开（公告）日：1988-12-27
• [EN] RECEPTOR COMPOUNDS BASED ON 1,7-DIOXA-4,10-DIAZACYCLODODECANE
  申请人：SCIMAT LIMITED

  公开号：WO1993005028A1

  公开（公告）日：1993-03-18

  (EN) Crown ether compounds which can function as receptor molecules for species such as alcohols, especially for ethanol, and other materials capable of forming hydrogen bonds. The compounds are based on 1,7-diaza-12-crown-4 group, substituted on the diaza groups with alkaryl groups as in formula (I) or with bridges extending to diaza groups on another 1,7-diaza-12-crown-4 group as in formula (II).(FR) On décrit des composés éther-couronne pouvant fonctionner comme molécules réceptrices pour des espèces telles que les alcools, en particulier l'éthanol, et autres matières capables de former des liaisons d'hydrogène. Les composés sont constitués à base d'un groupe 1,7-diaza-12-couronne-4, substitués au niveau des groupes diaza par des groupes alcaryles, tels que dans la formule (I), ou par des ponts s'étendant aux groupes diaza au niveau d'un autre groupe 1,7-diaza-12-couronne-4, tels que dans la formule (II).