3,3'-(3,6,9,12,15-pentaoxaheptadecane-1,17-diyldioxy)bis(2-hydroxybenzaldehyde) | 115142-68-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3'-(3,6,9,12,15-pentaoxaheptadecane-1,17-diyldioxy)bis(2-hydroxybenzaldehyde)
• 英文别名: 3-[2-[2-[2-[2-[2-[2-(3-Formyl-2-hydroxyphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-2-hydroxybenzaldehyde
• CAS: 115142-68-2
• 化学式: C₂₆H₃₄O₁₁
• 分子量: 522.549
• InChiKey: VYYSQJYVWLQHFA-UHFFFAOYSA-N

物化性质

• 沸点：
  656.4±55.0 °C(predicted)
• 密度：
  1.257±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  37
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,3'-(3,6,9,12,15-pentaoxaheptadecane-1,17-diyldioxy)bis(2-hydroxybenzaldehyde) 在 sodium tetrahydroborate 、 barium(II) perchlorate 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 1,2,9,10,12,13,15,16,18,19,21,22,24,25,32,33-hexadecahydro-3,7;27,31-dimetheno-8,11,14,17,20,23,26,1,33-benzoheptaoxadiazacyclopentatriacontine-38,39-diol
  参考文献：
  名称：

  Synthetic molecular receptors for urea. Macrocyclic ligands with intraannular acidic groups and the complexes with urea

  摘要：

  DOI：

  10.1021/ja00232a028
• 作为产物：
  描述：

  3-[2-[2-[2-[2-[2-[2-(3-Formyl-2-prop-2-enoxyphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-2-prop-2-enoxybenzaldehyde 在 palladium on activated charcoal 高氯酸 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以88%的产率得到3,3'-(3,6,9,12,15-pentaoxaheptadecane-1,17-diyldioxy)bis(2-hydroxybenzaldehyde)
  参考文献：
  名称：

  合成大环主体中中性客体和亲电子金属阳离子的共络合

  摘要：

  Synthese de pyrido-27-crown-9 • LiClO 4 uree ou Li et 1 uree Sont encapsulees par la分子热，et l'uree coordinee au Li par l'atome O. On synthetise egalement des complexes de Ni-eau et Ni -uree de 2 macrocycles avec reste base de Schiff

  DOI：

  10.1021/ja00223a017

文献信息

• Cocomplexation of neutral guests and electrophilic metal cations in synthetic macrocyclic hosts
  作者：Catherina J. Van Staveren、Johan. Van Eerden、Frank C. J. M. Van Veggel、Sybolt. Harkema、David N. Reinhoudt

  DOI：10.1021/ja00223a017

  日期：1988.7

  Synthese de pyrido-27-crown-9 • LiClO 4 uree ou Li et 1 uree sont encapsulees par la molecule-hote, et l'uree coordinee au Li par l'atome O. On synthetise egalement des complexes de Ni-eau et Ni-uree de 2 macrocycles avec reste base de Schiff

  Synthese de pyrido-27-crown-9 • LiClO 4 uree ou Li et 1 uree Sont encapsulees par la分子热，et l'uree coordinee au Li par l'atome O. On synthetise egalement des complexes de Ni-eau et Ni -uree de 2 macrocycles avec reste base de Schiff
• Synthetic molecular receptors for urea. Macrocyclic ligands with intraannular acidic groups and the complexes with urea
  作者：Catherina J. Van Staveren、Veronika M. L. J. Aarts、Peter D. J. Grootenhuis、Wichert J. H. Droppers、Johan. Van Eerden、Sybolt. Harkema、David N. Reinhoudt

  DOI：10.1021/ja00232a028

  日期：1988.11
• Molecular recognition of polar neutral molecules by metallomacrocycles: synthesis, proton NMR spectroscopy, x-ray structure, electrochemistry, and ab initio calculations
  作者：Arie R. Van Doorn、Robert Schaafstra、Martinus Bos、Sybolt Harkema、Johan Van Eerden、Willem Verboom、David N. Reinhoudt

  DOI：10.1021/jo00021a024

  日期：1991.10

  Metallomacrocycles 5 possessing an immobilized Lewis acidic uranyl group were synthesized by reaction of aldehydes 4 with cis-1,2-cyclohexanediamine in the presence of Ba2+ as a template cation and subsequent transmetallation with UO2(2+). These metallomacrocycles are soluble in organic solvents and the complexation with neutral molecules was investigated by polarography, H-1 NMR spectroscopy, solid-liquid and liquid-liquid extraction experiments, X-ray structure determinations, and ab initio calculations. Several solid complexes (6) of metallomacrocycles 5b-d with polar neutral molecules (formamide, acetamide, N-methylurea, hydroxyurea, urea, and DMSO) were isolated; a ring size selective complexation is observed. Polarography demonstrated a ring size affinity with the following stability order for the complexes in CH3CN: urea > N-methylurea > acetamide almost-equal-to formamide > acetone almost-equal-to 0. The stability constants of the 6b-urea and 6c-urea complexes in CDCl3 are according to H-1 NMR spectroscopy at least 10(8) M-1; the highest number ever achieved by a complex consisting of a neutral monometalloreceptor and a neutral molecule. The high stabilities were confirmed by solid-liquid and liquid-liquid extraction experiments. The crystal structures of the 6b-urea and 6d-urea complexes reveal that urea is encapsulated in the cavity and that the complexes are stabilized by coordination of the carbonyl oxygen of urea to the immobilized uranyl cation, multiple H-bond formation, and electrostatic interactions between urea nitrogens and ether oxygens. Ab initio calculations suggest that charge transfer determines the coordination between the uranyl cation and urea. The optimal coordination angle (C = O...M2+) is approximately 130-degrees, for both in-plane and perpendicular coordination.