7,16-bis(2-hydroxy-5-methoxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane | 168280-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 7,16-bis(2-hydroxy-5-methoxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• 英文别名: 2-[[16-[(2-Hydroxy-5-methoxyphenyl)methyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]methyl]-4-methoxyphenol
• CAS: 168280-25-9
• 化学式: C₂₈H₄₂N₂O₈
• 分子量: 534.65
• InChiKey: CYPNDHZZFIXFLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,N-双(甲氧基甲基)二氮-18-冠-6 、 7,16-bis(2-hydroxy-5-methoxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 以 xylene 为溶剂， 反应 24.0h， 以14%的产率得到51,52-dihydroxy-5,22-dimethoxy-12,15,29,32,37,40,45,48-octaoxa-1,9,18,26-tetraazapentacyclo<24.8.8.8.1^3,7.1^20,24>dipentaconta-3,5,7(51),20,22,24(52)-hexaene
  参考文献：
  名称：

  A New Approach to the Synthesis of Phenol-Containing Macroheterocycles

  摘要：

  A one-step method for the synthesis of new phenol-containing cryptands and cryptohemispherands by treating N,N'-bis(methoxymethyl)diazacrowns with the appropriate bis- and trisphenols is reported. This method, based on a special Mannich reaction, gives cyclized products without-the need for protecting groups and high dilution conditions. Unusually high yields of cryptohemisherands were realized using a relatively high concentration of the starting materials (50 mmol/L) and in the absence of metal cations as template agents in the reaction mixture. These excellent yields can be explained by intramolecular hydrogen bonding which prevents polycondensation. This new method also allowed preparation of new phenol-containing cylindrical tricyclic ligands by first forming bisphenol-substituted diaza-18-crown-6 at 80 degrees C followed by its reaction with a second bis(methoxymethyl)-substituted diaza-18-crown-6 at 144 degrees C. Crystal structures of two cryptohemispherands are reported herein. A shorter internal distance between N and O atoms in 27 as compared to 6 (R = NO2, n = m = 2) indicates intramolecular hydrogen bonding in phenol-containing macrocycle 27.

  DOI：

  10.1021/jo00120a040
• 作为产物：
  描述：

  N,N-双(甲氧基甲基)二氮-18-冠-6 、 4-甲氧基苯酚 以 四氯化碳 为溶剂， 以61%的产率得到7,16-bis(2-hydroxy-5-methoxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
  参考文献：
  名称：

  A New Approach to the Synthesis of Phenol-Containing Macroheterocycles

  摘要：

  A one-step method for the synthesis of new phenol-containing cryptands and cryptohemispherands by treating N,N'-bis(methoxymethyl)diazacrowns with the appropriate bis- and trisphenols is reported. This method, based on a special Mannich reaction, gives cyclized products without-the need for protecting groups and high dilution conditions. Unusually high yields of cryptohemisherands were realized using a relatively high concentration of the starting materials (50 mmol/L) and in the absence of metal cations as template agents in the reaction mixture. These excellent yields can be explained by intramolecular hydrogen bonding which prevents polycondensation. This new method also allowed preparation of new phenol-containing cylindrical tricyclic ligands by first forming bisphenol-substituted diaza-18-crown-6 at 80 degrees C followed by its reaction with a second bis(methoxymethyl)-substituted diaza-18-crown-6 at 144 degrees C. Crystal structures of two cryptohemispherands are reported herein. A shorter internal distance between N and O atoms in 27 as compared to 6 (R = NO2, n = m = 2) indicates intramolecular hydrogen bonding in phenol-containing macrocycle 27.

  DOI：

  10.1021/jo00120a040

文献信息

• A New One-Pot Synthesis of Double-Armed Ionizable Crown Ethers Using the Mannich Reaction
  作者：Ki-Whan Chi、Han-Chao Wei、Thomas Kottke、Richard J. Lagow

  DOI：10.1021/jo960332f

  日期：1996.1.1
• A New Approach to the Synthesis of Phenol-Containing Macroheterocycles
  作者：Andrei V. Bordunov、Nikolai G. Lukyanenko、Victor N. Pastushok、Krzysztof E. Krakowiak、Jerald S. Bradshaw、N. Kent Dalley、Xiaolan Kou

  DOI：10.1021/jo00120a040

  日期：1995.7

  A one-step method for the synthesis of new phenol-containing cryptands and cryptohemispherands by treating N,N'-bis(methoxymethyl)diazacrowns with the appropriate bis- and trisphenols is reported. This method, based on a special Mannich reaction, gives cyclized products without-the need for protecting groups and high dilution conditions. Unusually high yields of cryptohemisherands were realized using a relatively high concentration of the starting materials (50 mmol/L) and in the absence of metal cations as template agents in the reaction mixture. These excellent yields can be explained by intramolecular hydrogen bonding which prevents polycondensation. This new method also allowed preparation of new phenol-containing cylindrical tricyclic ligands by first forming bisphenol-substituted diaza-18-crown-6 at 80 degrees C followed by its reaction with a second bis(methoxymethyl)-substituted diaza-18-crown-6 at 144 degrees C. Crystal structures of two cryptohemispherands are reported herein. A shorter internal distance between N and O atoms in 27 as compared to 6 (R = NO2, n = m = 2) indicates intramolecular hydrogen bonding in phenol-containing macrocycle 27.