1-[bis(N,N-diethoxycarbonylmethyl)aminomethyl]-3,5-bis[(6-methyl-pyridin-2-yl)-aminomethyl]-2,4,6-trimethylbenzene

• 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: 1-[bis(N,N-diethoxycarbonylmethyl)aminomethyl]-3,5-bis[(6-methyl-pyridin-2-yl)-aminomethyl]-2,4,6-trimethylbenzene
• 英文别名: Ethyl 2-[(2-ethoxy-2-oxoethyl)-[[2,4,6-trimethyl-3,5-bis[[(6-methylpyridin-2-yl)amino]methyl]phenyl]methyl]amino]acetate
• 化学式: C₃₂H₄₃N₅O₄
• 分子量: 561.725
• InChiKey: BWCXVZMRWKOHNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[bis(N,N-diethoxycarbonylmethyl)aminomethyl]-3,5-bis[(6-methyl-pyridin-2-yl)-aminomethyl]-2,4,6-trimethylbenzene 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Carboxylate-Based Receptors for the Recognition of Carbohydrates in Organic and Aqueous Media

  摘要：

  Acyclic receptors containing neutral and ionic hydrogen-bonding sites, such as amino-pyridine and carboxylate groups, were prepared and their binding properties toward neutral sugar molecules were studied. The bindin g studies with disodium and bis(tetramethylammonium) salts containing the dianion 11 have revealed that this type of receptor molecule is able to recognize the selected sugars in both organic and aqueous media. The carboxylate/pyridine-based receptor 11 exhibits in chloroform at least a 100-fold higher affinity for glucopyranosides than the previously described triarmed pyridine-based receptor 1, incorporating only neutral hydrogen-bonding sites. A substantial drop in the association constants is expectedly observed for an ester analogue of 11, compound 9. The dicarboxylate 11 is able to form complexes in water with methyl P-D-glucopyranoside and D-cellobiose, with a preference for the disaccharide. The studies show the importance of charge-reinforced hydrogen bonds in the recognition of carbohydrates.

  DOI：

  10.1021/jo052479p
• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 、 亚氨基二乙酸二乙酯 、 2,4,6-三溴甲基三甲基苯 在 potassium carbonate 作用下， 以 乙腈 、 四氢呋喃 为溶剂， 反应 48.75h， 以33%的产率得到1-[bis(N,N-diethoxycarbonylmethyl)aminomethyl]-3,5-bis[(6-methyl-pyridin-2-yl)-aminomethyl]-2,4,6-trimethylbenzene
  参考文献：
  名称：

  Carboxylate-Based Receptors for the Recognition of Carbohydrates in Organic and Aqueous Media

  摘要：

  Acyclic receptors containing neutral and ionic hydrogen-bonding sites, such as amino-pyridine and carboxylate groups, were prepared and their binding properties toward neutral sugar molecules were studied. The bindin g studies with disodium and bis(tetramethylammonium) salts containing the dianion 11 have revealed that this type of receptor molecule is able to recognize the selected sugars in both organic and aqueous media. The carboxylate/pyridine-based receptor 11 exhibits in chloroform at least a 100-fold higher affinity for glucopyranosides than the previously described triarmed pyridine-based receptor 1, incorporating only neutral hydrogen-bonding sites. A substantial drop in the association constants is expectedly observed for an ester analogue of 11, compound 9. The dicarboxylate 11 is able to form complexes in water with methyl P-D-glucopyranoside and D-cellobiose, with a preference for the disaccharide. The studies show the importance of charge-reinforced hydrogen bonds in the recognition of carbohydrates.

  DOI：

  10.1021/jo052479p

文献信息

• Carboxylate-Based Receptors for the Recognition of Carbohydrates in Organic and Aqueous Media
  作者：Monika Mazik、Hüseyin Cavga

  DOI：10.1021/jo052479p

  日期：2006.4.1

  Acyclic receptors containing neutral and ionic hydrogen-bonding sites, such as amino-pyridine and carboxylate groups, were prepared and their binding properties toward neutral sugar molecules were studied. The bindin g studies with disodium and bis(tetramethylammonium) salts containing the dianion 11 have revealed that this type of receptor molecule is able to recognize the selected sugars in both organic and aqueous media. The carboxylate/pyridine-based receptor 11 exhibits in chloroform at least a 100-fold higher affinity for glucopyranosides than the previously described triarmed pyridine-based receptor 1, incorporating only neutral hydrogen-bonding sites. A substantial drop in the association constants is expectedly observed for an ester analogue of 11, compound 9. The dicarboxylate 11 is able to form complexes in water with methyl P-D-glucopyranoside and D-cellobiose, with a preference for the disaccharide. The studies show the importance of charge-reinforced hydrogen bonds in the recognition of carbohydrates.