(S)-N,N-diethyl-2-(6-methoxynaphth-2-yl)propionamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-N,N-diethyl-2-(6-methoxynaphth-2-yl)propionamide
• 英文别名: N,N-diethyl-2-(6-methoxy-2-naphthyl)propionamide；(2S)-N,N-diethyl-2-(6-methoxynaphthalen-2-yl)propanamide
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: GMVATKRDNVYKDJ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  萘普生 、 二乙胺 在 1-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-N,N-diethyl-2-(6-methoxynaphth-2-yl)propionamide
  参考文献：
  名称：

  胺在不对称萘基二元化合物的荧光猝灭中的波长依赖性立体分化。

  摘要：

  在本论文中，波长已用作可调参数，以实现对由萘单元（即6-甲氧基萘（NPX）和1-甲基萘（NAP）衍生物）组成的两种新型不对称双发色团的光物理的选择性控制。电子特性，通过酰胺间隔基[（S，S）和（S，R）-NPX-NAP]连接。作为模型系统，还研究了相关的发色化合物（NPX-M和NAP-M）。在325 nm激发时，光能保留在NPX部分中，而在290 nm时，从NAP单元到NPX发色团的有效单线态-单态-单态能量转移（phi（SSET）约为97％）。通过激基复合物形成的三乙胺在激发态猝灭中观察到了显着的立体分化。结果表明，可以通过波长调谐来控制激发态下与构型有关的相互作用。这可以通过pi系统的分子内相互作用导致氧化还原特性的调节而合理化。

  DOI：

  10.1021/jp047996a

文献信息

• ——
  作者：Horst Weber、Uta Steimer、Raimund Mannhold、Gabriele Cruciani

  DOI：10.1023/a:1011021024254

  日期：——

  Purpose. To synthesize new naproxen (01) derivatives with amide or ester structures or with a combination of the two (02-15). To compare their physicochemical properties with naproxen esters (16-22) and their respective skin permeation behavior. To study structure-permeation relationships via partial least squares (PLS)-analysis.Methods. Stability, aqueous, and octanol solubility were determined. Lipophilicity and further 53 chemical descriptors were computed. A suitable bz-vitro skin permeation model was developed to compare maximal flux (J(max)) of derivatives. Based on these flux data, PLS-analysis was performed to derive structure-permeation relationships.Results, None of the new derivatives showed an improved flux in comparison to naproxen. This result can be explained by PLS-analysis: skin permeation increases with the solubility both in water and in octanol. For a good permeation, an optimized molecule should exhibit a small volume with a spherical shape. The surface area should be large in relation to volume, as indicated by the rugosity parameter. A clear separation between the hydrophobic and the hydrophilic domain (= high amphiphilic moment) is favorable. Lipophilicity is inversely correlated with skin permeation.Conclusions. PLS-analysis is a valuable tool to derive significant, internally predictive quantitative models for structure-permeation relationships of naproxen derivatives in the above described skin permeation assay.