Ditert-butylphosphorylmethyl 3-[5-[3-(ditert-butylphosphorylmethoxy)-3-oxopropyl]pyridin-3-yl]propanoate | 1450821-18-7

• 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: Ditert-butylphosphorylmethyl 3-[5-[3-(ditert-butylphosphorylmethoxy)-3-oxopropyl]pyridin-3-yl]propanoate
• 英文别名: ditert-butylphosphorylmethyl 3-[5-[3-(ditert-butylphosphorylmethoxy)-3-oxopropyl]pyridin-3-yl]propanoate
• CAS: 1450821-18-7
• 化学式: C₂₉H₅₁NO₆P₂
• 分子量: 571.675
• InChiKey: GPCRMLZFJUDRLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  99.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  pyridine-3,5-bis(propionic acid) 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 3.0h， 生成 Ditert-butylphosphorylmethyl 3-[5-[3-(ditert-butylphosphorylmethoxy)-3-oxopropyl]pyridin-3-yl]propanoate
  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

• 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.