7,16-bis(5-t-butyl-2-hydroxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7,16-bis(5-t-butyl-2-hydroxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• 英文别名: N,N'-bis(4-tert-butylphenol-2-ylmethyl)diaza-18-crown-6；4-Tert-butyl-2-[[16-[(5-tert-butyl-2-hydroxyphenyl)methyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]methyl]phenol
• 化学式: C₃₄H₅₄N₂O₆
• 分子量: 586.813
• InChiKey: WENNHJKDIHPGPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-双甲苯氧基乙烷 、 7,16-bis(5-t-butyl-2-hydroxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 在 sodium 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 以82%的产率得到5,16-Ditert-butyl-9,12,23,26,31,34-hexaoxa-1,20-diazatetracyclo[18.8.8.03,8.013,18]hexatriaconta-3(8),4,6,13(18),14,16-hexaene
  参考文献：
  名称：

  Macrocyclic ligand design. A synthetic, solvent extraction, computational and NMR study of the effect of cryptand flexibility on sodium ion affinity†

  摘要：

  一系列包含 N2O6 供体的穴状配体的刚性已被证明对此类物质络合钠离子的能力有显着影响。 X 射线和相关的计算研究，包括分子力学、半经验 (AM1) 和从头算（密度泛函）研究，加上苦味酸钠提取实验和 NMR 研究的结果，已被用来探讨影响钠的构象方面沿配体系列的离子络合。结论是，穴状配体能够采用内-内构象的难易程度是影响这些系统中包容性金属离子结合发生的重要因素。

  DOI：

  10.1039/b102585f
• 作为产物：
  描述：

  聚合甲醛 、 4-叔丁基苯酚 、 二氮杂18-冠醚-6 以 甲苯 为溶剂， 生成 7,16-bis(5-t-butyl-2-hydroxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
  参考文献：
  名称：

  含酚氮杂大环化合物的合成及碱性阳离子的液膜转运

  摘要：

  摘要 两种新的含双酚二氮杂冠醚衍生物，7,16-双(2-羟基-5-乙基苯甲酸苄基)-1,4,10,13-四氧杂-7,16-二氮杂环十八烷 (1) 和 7,16-双( 2-羟基-3,4-二甲基苄基)-1,4,10,13-四氧杂-7,16-二氮杂环十八烷 (2)，已通过一锅曼尼希反应合成。化合物1的结构特征。使用这两种新的二氮杂大环和另一种先前制备的二氮杂大环衍生物 7,16-双(3-羟基-6-甲基-2-吡啶基甲基)-1,4,10,13-四氧杂-7 进行碱金属阳离子的液膜传输还研究了 ,16-二氮杂环十八烷 (3) 作为离子载体。结果表明，阳离子传输速率与氮供体数量和取代基团的空间效应密切相关。与其他大环化合物相比，

  DOI：

  10.1016/j.molstruc.2004.08.002

文献信息

• Syntheses and aggregate study of bisphenol-containing diaza-18-crown-6 ligands
  作者：Ning Su、Jerald S. Bradshaw、Paul B. Savage、Krzysztof E. Krakowiak、Reed M. Izatt、Stephen L. De Wall、George W. Gokel

  DOI：10.1016/s0040-4020(99)00555-4

  日期：1999.8

  Bisphenol-containing diaza-18-crown-6 ligands (1-16) were synthesized as potential membrane-forming amphiphiles via the one-pot Mannich reaction. Sonication of the crude products in a small amount of MeOH followed by filtration and drying proved to be an efficient method of purifying nearly all compounds. Compounds 8 and 9 were selected for assay as amphiphiles. Compared to simple, alkylated diazacrown ethers, the stability of the amphisomes formed from these monomers is lower possibly because intramolecular hydrogen bonding prevents formation of intermolecular hydrogen bonds. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Eco-Friendly Synthesis of Novel Lariat Ethers via Mannich Reaction under Solventless Conditions
  作者：Hashem Sharghi、Reza Khalifeh

  DOI：10.3987/com-07-11044

  日期：——

  An expeditious solventless synthesis of novel lariat ethers using calcium oxide (CaO) via Mannich reaction are herein described. This methodology eliminates the use of excess of solvent during the course of reaction. The reaction time is brought down from hours to minutes (20-30 minutes) along with yield enhancement. The CaO powder can be reused up to three times after simple washing with acetone.
• 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
• Syntheses and crystal structures of copper complexes of 7,16-bis (5-t-butyl-2-hydroxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
  作者：Shu-Lan Ma、Wen-Xiang Zhu、Miao-Qiong Xu、Ying-Li Wang、Qian-Ling Guo、Ying-Chun Liu

  DOI：10.1016/j.poly.2003.06.002

  日期：2003.11

  Reaction of the crown ether ligand H2L (H2L = 7,16-bis (5-t-butyl-2-hydroxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane) with Cu(AC)(2) and Cu(NO3)(2) affords complexes 1 and 2, respectively, which are characterized by elemental analysis, IR and UV-Visible spectroscopy and X-ray diffraction. Both crystal structure analysis and spectroscopy study unexpectedly showed that the two side-arm p-tert-butylphenols of the original crown ether are converted to nitro p-tert-butylphenols in complex 2. In each complex the copper (II) ion is coordinated to two nitrogen and four oxygen atoms, two from the crown ether ring and other two from the deprotonated phenolate groups, which define an elongated octahedron. Electrochemical studies indicate that the two complexes undergo irreversible reduction in DMF solution. (C) 2003 Elsevier Ltd. All rights reserved.