2,2-dibutyl-[1,3,6,2]trioxastannocane | 14583-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dibutyl-[1,3,6,2]trioxastannocane
• 英文别名: 2,2-Dibutyl-[1,3,6,2]trioxastannocan
• CAS: 14583-69-8
• 化学式: C₁₂H₂₆O₃Sn
• 分子量: 337.047
• InChiKey: OIGNTJWVKBIJJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1H-吡唑-3,5-二甲酰氯 、 2,2-dibutyl-[1,3,6,2]trioxastannocane 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 生成 25(26),27(28)-H,H-3,6,9,15,18,21-hexaoxa-25,26,27,28-tetraazatricycle<2.1.2.1.2^11,13>octacosa-1(26),13(28),11,23-tetraen-2,10,14,22-tetraone
  参考文献：
  名称：

  A Proton-Ionizable Ester Crown of 3,5-Disubstituted 1H-Pyrazole Able To Form Stable Dinuclear Complexes with Lipophilic Phenethylamines

  摘要：

  A convenient synthesis of the proton-ionizable crown 3 is reported that uses dibutyltin oxide. In acetonitrile, the reaction of 3 (LH2) with phenethylamine and homoveratrylamine (molar ratio 1:2) affords solid dinuclear complexes [LH2]2RNH(2) (4a,b), which spectroscopic (FAB-MS, IR, H-1 and C-13 NMR) data point toward a strong participation of the pyrazole nitrogens in the amine complexation. In DMSO-d(6) solution, a C-13 MMR study demonstrates the formation in situ of analogous neutral 4a-d[LH2]2RNH(2) or charged 5a-d[L2-]2RNH(3)(+) dinuclear complexes by reaction of 3 [LH2] or 3'[L2-]2Na(+) with RNH2 (phenethylamine, homoveratrylamine, dopamine, and norepinephrine) or their RNH3+Cl- salts, respectively. Differences between the structure of complexes 4 and 5 have been evaluated by taking the homoveratrylamine derivatives 4b and 5b as models. An H-1 and C-13 NMR study (by raising the temperature) and measurements of intermolecular NOE effects (from NOESY and ROESY spectral demonstrate that both complexes behave as prototropic isomers showing different conformations. By increasing the ionic strength, the 4b isomer structure becomes similar to that of 5b. The molecular modeling (GenMol software) of 4a-d and 5a-d shows that the assemblage in which both amine molecules are on the same side of the crown is the more stable. Lipophilic amines afford more stable complexes than hydrophilic ones and charged species are much more stable than the neutral ones.

  DOI：

  10.1021/jo9623651
• 作为产物：
  描述：

  二乙二醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 xylene 作用下， 生成 2,2-dibutyl-[1,3,6,2]trioxastannocane
  参考文献：
  名称：

  Woronkow; Romadan, Khimiya Geterotsiklicheskikh Soedinenii, 1966, vol. 2, p. 892,894;engl.Ausg.S.682,684

  摘要：

  DOI：

文献信息

• A Proton-Ionizable Ester Crown of 3,5-Disubstituted 1<i>H</i>-Pyrazole Able To Form Stable Dinuclear Complexes with Lipophilic Phenethylamines
  作者：Lucrecia Campayo、José M. Bueno、Pilar Navarro、Carmen Ochoa、Jesús Jimenez-Barbero、Gèrard Pèpe、André Samat

  DOI：10.1021/jo9623651

  日期：1997.5.1

  A convenient synthesis of the proton-ionizable crown 3 is reported that uses dibutyltin oxide. In acetonitrile, the reaction of 3 (LH2) with phenethylamine and homoveratrylamine (molar ratio 1:2) affords solid dinuclear complexes [LH2]2RNH(2) (4a,b), which spectroscopic (FAB-MS, IR, H-1 and C-13 NMR) data point toward a strong participation of the pyrazole nitrogens in the amine complexation. In DMSO-d(6) solution, a C-13 MMR study demonstrates the formation in situ of analogous neutral 4a-d[LH2]2RNH(2) or charged 5a-d[L2-]2RNH(3)(+) dinuclear complexes by reaction of 3 [LH2] or 3'[L2-]2Na(+) with RNH2 (phenethylamine, homoveratrylamine, dopamine, and norepinephrine) or their RNH3+Cl- salts, respectively. Differences between the structure of complexes 4 and 5 have been evaluated by taking the homoveratrylamine derivatives 4b and 5b as models. An H-1 and C-13 NMR study (by raising the temperature) and measurements of intermolecular NOE effects (from NOESY and ROESY spectral demonstrate that both complexes behave as prototropic isomers showing different conformations. By increasing the ionic strength, the 4b isomer structure becomes similar to that of 5b. The molecular modeling (GenMol software) of 4a-d and 5a-d shows that the assemblage in which both amine molecules are on the same side of the crown is the more stable. Lipophilic amines afford more stable complexes than hydrophilic ones and charged species are much more stable than the neutral ones.
• Woronkow; Romadan, Khimiya Geterotsiklicheskikh Soedinenii, 1966, vol. 2, p. 892,894;engl.Ausg.S.682,684
  作者：Woronkow、Romadan

  DOI：——

  日期：——