[2-(Diethylamino)-2-oxoethyl] 3-pyridin-3-ylpropanoate | 1450821-13-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [2-(Diethylamino)-2-oxoethyl] 3-pyridin-3-ylpropanoate
• 英文别名: [2-(diethylamino)-2-oxoethyl] 3-pyridin-3-ylpropanoate
• CAS: 1450821-13-2
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: BWNVFMPMLPRBTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Zn(5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrinate) 、 [2-(Diethylamino)-2-oxoethyl] 3-pyridin-3-ylpropanoate 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Influence of non-covalent preorganization on supramolecular effective molarities

  摘要：

  在一组卟啉-吡啶配合物中，形成氢键相互作用限制了柔性连接器的构象运动，但对螯合协同作用没有影响。

  DOI：

  10.1039/c5ob00231a
• 作为产物：
  描述：

  3-(3-吡啶基)丙酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 [2-(Diethylamino)-2-oxoethyl] 3-pyridin-3-ylpropanoate
  参考文献：
  名称：

  Relationship between Chemical Structure and Supramolecular Effective Molarity for Formation of Intramolecular H-Bonds

  摘要：

  Effective molarity (EM) is a key parameter that determines the efficiency of a range of supramolecular phenomena from the folding of macromolecules to multivalent ligand binding. Coordination complexes formed between zinc porphyrins equipped H-bond donor sites and pyridine ligands equipped with H-bond acceptor sites have allowed systematic quantification of EM values for the formation of intramolecular H-bonds in 240 different systems. The results provide insights into the relationship of EM to supramolecular architecture, H-bond strength, and solvent. Previous studies on ligands equipped with phosphonate diester and ether H-bond acceptors were inconclusive, but the experiments described here on ligands equipped with phosphine oxide, amide, and ester H-bond acceptors resolve these ambiguities. Chemical double-mutant cycles were used to dissect the thermodynamic contributions of individual H-bond interactions to the overall stabilities of the complexes and hence determine the values of EM, which fall in the range 1-1000 mM. Solvent has little effect on EM, and the values measured in toluene and 1,1,2,2-tetrachloroethane are similar. For H-bond acceptors that have similar geometries but different H-bond strengths (amide and ester), the values of EM are very similar. For H-bond acceptors that have different geometries but similar H-bond strengths (amide and phosphonate diester), there is, little correlation between the values of EM. These results imply that supramolecular EMs are independent of solvent and intrinsic H-bond strength but depend on supramolecular architecture and geometric complementarity.

  DOI：

  10.1021/ja406235d

文献信息

• Influence of receptor flexibility on intramolecular H-bonding interactions
  作者：Hongmei Sun、Kai Guo、Haifeng Gan、Xin Li、Christopher A. Hunter

  DOI：10.1039/c5ob00805k

  日期：——

  Atropisomers of a series of zinc tetraphenyl porphyrins were synthesized and used as supramolecular receptors. Rotation around the porphyrin-meso phenyl bonds is restricted by installing ortho-chlorine substituents on the phenyl groups. The chlorine substituents allowed chromatographic separation of atropisomers, which did not interconvert at room temperature. The porphyrin meso phenyl groups were

  合成了一系列四苯基锌卟啉锌的阻转异构体，并将其用作超分子受体。围绕卟啉-内消旋苯基键的旋转通过在苯基上安装邻氯取代基来限制。氯取代基可以色谱分离阻转异构体，在室温下不会互变。卟啉介观苯基还带有酚基，当卟啉锌与配有酯或酰胺侧臂的吡啶配体结合时，会导致分子内氢键的形成。将吡啶配体与构象锁定的氯卟啉的结合与相应的未取代的卟啉进行了比较，后者更为灵活。在两种不同的溶剂甲苯和1,1,2,2-四氯乙烷（TCE）中测量了150种卟啉-吡啶锌配合物的缔合常数。然后将这些缔合常数用于构建120个化学双突变周期，以量化氯取代对在卟啉的酚侧臂与吡啶配体的酯或酰胺侧臂之间形成的分子内H键的自由能的影响。-1。
• Relationship between Chemical Structure and Supramolecular Effective Molarity for Formation of Intramolecular H-Bonds
  作者：Hongmei Sun、Christopher A. Hunter、Cristina Navarro、Simon Turega

  DOI：10.1021/ja406235d

  日期：2013.9.4

  Effective molarity (EM) is a key parameter that determines the efficiency of a range of supramolecular phenomena from the folding of macromolecules to multivalent ligand binding. Coordination complexes formed between zinc porphyrins equipped H-bond donor sites and pyridine ligands equipped with H-bond acceptor sites have allowed systematic quantification of EM values for the formation of intramolecular H-bonds in 240 different systems. The results provide insights into the relationship of EM to supramolecular architecture, H-bond strength, and solvent. Previous studies on ligands equipped with phosphonate diester and ether H-bond acceptors were inconclusive, but the experiments described here on ligands equipped with phosphine oxide, amide, and ester H-bond acceptors resolve these ambiguities. Chemical double-mutant cycles were used to dissect the thermodynamic contributions of individual H-bond interactions to the overall stabilities of the complexes and hence determine the values of EM, which fall in the range 1-1000 mM. Solvent has little effect on EM, and the values measured in toluene and 1,1,2,2-tetrachloroethane are similar. For H-bond acceptors that have similar geometries but different H-bond strengths (amide and ester), the values of EM are very similar. For H-bond acceptors that have different geometries but similar H-bond strengths (amide and phosphonate diester), there is, little correlation between the values of EM. These results imply that supramolecular EMs are independent of solvent and intrinsic H-bond strength but depend on supramolecular architecture and geometric complementarity.
• Influence of non-covalent preorganization on supramolecular effective molarities
  作者：Hongmei Sun、Cristina Navarro、Christopher A. Hunter

  DOI：10.1039/c5ob00231a

  日期：——

  Formation of H-bonding interactions, which restrict the conformational mobility of a flexible linker, have no effect on chelate cooperativity in a family of porphyrin-pyridine complexes.

  在一组卟啉-吡啶配合物中，形成氢键相互作用限制了柔性连接器的构象运动，但对螯合协同作用没有影响。