3,4-(42-cerown-14)benzaldehyde | 200293-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-(42-cerown-14)benzaldehyde
• CAS: 200293-43-2
• 化学式: C₃₃H₅₆O₁₅
• 分子量: 692.799
• InChiKey: VIHBTHQJKCJHQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  48.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  146.29
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3,4-(42-cerown-14)benzaldehyde 在 sodium tetrahydroborate 、 potassium iodide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 66.0h， 生成 3,4-(42-crown-14)benzyl dodecyl ether
  参考文献：
  名称：

  Synthesis and Mass Spectrometry Studies of an Amphiphilic Polyether-Based Rotaxane That Lacks an Enthalpic Driving Force for Threading

  摘要：

  A pure amphiphilic macrocrown ether (MC-12) was obtained by removing linear oligomers and larger macrocycles at the macrocyclization step, before proceeding with an established synthetic procedure. This pure MC-12 was used to synthesize a rotaxane composed of one MC-12 ring threaded with one end-capped poly(tetrahydrofuran) (PTHF) oligomer by equilibrating half an equivalent of the thread with an organized solution of MC-12 and end-capping the threads with excess 2-p-[tris(p-tert-butylphenyl)methyl]phenoxymethyl-4,4-dimethylazlactone. The rotaxane was positively identified by matrix-assisted laser desorption/ionization time-of-flight (MALDI-ToF) mass spectrometry (MS), although the spectra showed a low abundance of the rotaxane ions and high abundances of unthreaded MC-12 and end-capped thread ions in the product isolated from the threading experiment. Analysis by GPC was inconclusive because both the rotaxane and a one-to-one complex elute at the same retention volume. MALDI-ToF and electrospray ionization quadrupole ion trap (ESI-QIT) MS analyses of the rotaxane sample and mixtures of MC-12 and end-capped thread, including studies using varying laser intensities, comparisons of linear and reflectron analysis modes of the ToF MS, and analysis of the rotaxane by the post-source decay method demonstrated that the rotaxane does not fragment during the MALDI-ToF MS analysis, although the rotaxane ionizes less efficiently than either of its two components. HPLC using silica columns and an eluant of THF with 0.3 wt % Aliquat 336 confirmed that a "further-purified" sample of the rotaxane mixture was composed of 66 wt % end-capped thread, 23 wt % MC-12, and 11 wt % rotaxane, in qualitative agreement with the corresponding MALDI-ToF mass spectrum.

  DOI：

  10.1021/ma0476689
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以19.4%的产率得到3,4-(42-cerown-14)benzaldehyde
  参考文献：
  名称：

  Synthesis and Mass Spectrometry Studies of an Amphiphilic Polyether-Based Rotaxane That Lacks an Enthalpic Driving Force for Threading

  摘要：

  A pure amphiphilic macrocrown ether (MC-12) was obtained by removing linear oligomers and larger macrocycles at the macrocyclization step, before proceeding with an established synthetic procedure. This pure MC-12 was used to synthesize a rotaxane composed of one MC-12 ring threaded with one end-capped poly(tetrahydrofuran) (PTHF) oligomer by equilibrating half an equivalent of the thread with an organized solution of MC-12 and end-capping the threads with excess 2-p-[tris(p-tert-butylphenyl)methyl]phenoxymethyl-4,4-dimethylazlactone. The rotaxane was positively identified by matrix-assisted laser desorption/ionization time-of-flight (MALDI-ToF) mass spectrometry (MS), although the spectra showed a low abundance of the rotaxane ions and high abundances of unthreaded MC-12 and end-capped thread ions in the product isolated from the threading experiment. Analysis by GPC was inconclusive because both the rotaxane and a one-to-one complex elute at the same retention volume. MALDI-ToF and electrospray ionization quadrupole ion trap (ESI-QIT) MS analyses of the rotaxane sample and mixtures of MC-12 and end-capped thread, including studies using varying laser intensities, comparisons of linear and reflectron analysis modes of the ToF MS, and analysis of the rotaxane by the post-source decay method demonstrated that the rotaxane does not fragment during the MALDI-ToF MS analysis, although the rotaxane ionizes less efficiently than either of its two components. HPLC using silica columns and an eluant of THF with 0.3 wt % Aliquat 336 confirmed that a "further-purified" sample of the rotaxane mixture was composed of 66 wt % end-capped thread, 23 wt % MC-12, and 11 wt % rotaxane, in qualitative agreement with the corresponding MALDI-ToF mass spectrum.

  DOI：

  10.1021/ma0476689