3,3'-bis<2-(2-propenyloxy)benzaldehyde> | 132939-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,3'-bis<2-(2-propenyloxy)benzaldehyde>
• 英文别名: 3-[[4-[2-[2-[4-[(3-Formyl-2-prop-2-enoxyphenoxy)methyl]phenoxy]ethoxy]ethoxy]phenyl]methoxy]-2-prop-2-enoxybenzaldehyde
• CAS: 132939-05-0
• 化学式: C₃₈H₃₈O₉
• 分子量: 638.714
• InChiKey: XTDDLWCYJCOHRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,3'-bis<2-(2-propenyloxy)benzaldehyde> 在 palladium diacetate 、 甲酸:三乙胺 1:1 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以98%的产率得到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 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 3,3'-bis<2-(2-propenyloxy)benzaldehyde>
  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

• Molecular recognition of neutral molecules by metalloclefts: synthesis, x-ray structure, proton NMR spectroscopy, electrochemistry, and molecular modeling
  作者：Arie R. Van Doorn、Martinus Bos、Sybolt Harkema、Johan Van Eerden、Willem Verboom、David N. Reinhoudt

  DOI：10.1021/jo00007a023

  日期：1991.3

  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.