naphtho-9-crown-3 ether | 36307-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphtho-9-crown-3 ether
• 英文别名: naphtho-9-crown-3；2,3,5,6-Tetrahydronaphtho[2,3-b][1,4,7]trioxonine；11,14,17-trioxatricyclo[8.7.0.03,8]heptadeca-1,3,5,7,9-pentaene
• CAS: 36307-54-7
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: HKBHRNFAVYXVGC-UHFFFAOYSA-N

物化性质

• 沸点：
  382.9±31.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  naphtho-9-crown-3 ether 在 硫酸 、 三氯化铁 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 以32.5%的产率得到7,8,10,11,7',8',10',11'-Octahydro-[5,5']bi[6,9,12-trioxa-cyclonona[b]naphthalenyl]
  参考文献：
  名称：

  Oxidative coupling of naphtho-9-crown-3 ether: X-ray crystal structure and solution and solid-state NMR analysis of the dimer

  摘要：

  用 FeCl3 和 H2SO4 水溶液处理萘-9-冠-3 醚可生成双-萘-9-冠-3 醚，收率约为 30%。该化合物在单斜 P21/n 空间群中结晶；a = 9.2004(9)，b = 18.0868(17)，c = 13.2078(13)埃，β = 97.799(2)°，Z = 4。1H 和 13C NMR 数据是在溶液中获得的，固态 13C NMR 图谱也包括在内，以供比较。发现固态中含氧脂肪族碳的化学位移范围约为 12 ppm，而溶液 13C NMR 光谱中的范围为 3 ppm。这些结果将根据晶体结构中碳位点的扭转环境进行讨论。

  DOI：

  10.1139/v01-166
• 作为产物：
  描述：

  二氯乙醚 、 2,3-二羟基萘 在 lithium hydroxide 作用下， 以 水 为溶剂， 反应 80.5h， 以4.8%的产率得到naphtho-9-crown-3 ether
  参考文献：
  名称：

  Synthesis, characterization and solid-phase 13C NMR of naphtho-9-crown-3

  摘要：

  The synthesis and characterization of naptho-9-crown-3, N9C3, as a novel 9-membered ring crown ether with greater lipophilicity than that of benzo-9-crown-3, B9C3, is reported. The solution AA'BB' pattern of -CH2O- protons in N9C3 is close to that of B9C3. The solid-phase C-13 CPMAS NMR, as a tool for conformation prediction, reveals that the solid-phase conformation of the 9-membered ring crown cavity in N9C3 is different from B9C3, the two key C2O2CH(2) and C3O1CH(2) units are predicted to be out of naphthalene plane, and the two C1C2O2CH(2) and C4C3O1CH(2) torsion angles are close to each other. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(00)00462-2

文献信息

• Synthesis, characterization and solid-phase 13C NMR of naphtho-9-crown-3
  作者：A Moghimi、M.F Rastegar、M Ghandi、G.W Buchanan、H Rahbarnoohi

  DOI：10.1016/s0022-2860(00)00462-2

  日期：2000.8

  The synthesis and characterization of naptho-9-crown-3, N9C3, as a novel 9-membered ring crown ether with greater lipophilicity than that of benzo-9-crown-3, B9C3, is reported. The solution AA'BB' pattern of -CH2O- protons in N9C3 is close to that of B9C3. The solid-phase C-13 CPMAS NMR, as a tool for conformation prediction, reveals that the solid-phase conformation of the 9-membered ring crown cavity in N9C3 is different from B9C3, the two key C2O2CH(2) and C3O1CH(2) units are predicted to be out of naphthalene plane, and the two C1C2O2CH(2) and C4C3O1CH(2) torsion angles are close to each other. (C) 2000 Elsevier Science B.V. All rights reserved.
• Oxidative coupling of naphtho-9-crown-3 ether: X-ray crystal structure and solution and solid-state NMR analysis of the dimer
  作者：G W Buchanan、M F Rastegar、G PA Yap、A Moghimi、M Ghandi

  DOI：10.1139/v01-166

  日期：2001.10.1

  Treatment of naphtho-9-crown-3 ether with FeCl₃ and aqueous H₂SO₄ generates bis-naphtho-9-crown-3 ether in ca. 30% yield. This compound crystallizes in the monoclinic P2₁/n space group; a = 9.2004(9), b = 18.0868(17), and c = 13.2078(13) Å, β = 97.799(2)° and Z = 4. ¹H and ¹³C NMR data have been obtained in solution, and the solid-state ¹³C NMR spectrum is included for comparison. A chemical shift range of ca. 12 ppm has been found for the oxygenated aliphatic carbons in the solid state, in contrast to the 3 ppm range in the solution ¹³C NMR spectrum. These results are discussed in terms of the torsional environments of the carbon sites in the crystal structure.Key words: crown ether, stereochemistry, oxidative dimerization.

  用 FeCl3 和 H2SO4 水溶液处理萘-9-冠-3 醚可生成双-萘-9-冠-3 醚，收率约为 30%。该化合物在单斜 P21/n 空间群中结晶；a = 9.2004(9)，b = 18.0868(17)，c = 13.2078(13)埃，β = 97.799(2)°，Z = 4。1H 和 13C NMR 数据是在溶液中获得的，固态 13C NMR 图谱也包括在内，以供比较。发现固态中含氧脂肪族碳的化学位移范围约为 12 ppm，而溶液 13C NMR 光谱中的范围为 3 ppm。这些结果将根据晶体结构中碳位点的扭转环境进行讨论。