| 1261295-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• CAS: 1261295-23-1
• 化学式: C₁₇H₁₂ClNO₂
• 分子量: 297.741
• InChiKey: FJUHSLLHOIGUIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.19
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  6-[2-[5-氯-2-[(2,4-二氟苯基)甲氧基]苯基]环戊烯-1-基]吡啶-2-羧酸 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  A spectroscopic and computational study of an electrocyclized photo-degradation product of 6-(2-(5-chloro-2-(2,4-difluorobenyzloxy)phenyl)cyclopent-1-enyl)picolinic acid

  摘要：

  An unusual electrocyclized photo-degradation product of an EP1 antagonist drug candidate, 6-(2-(5-chloro-2-(2,4-difluorobenyzloxy) phenyl) cyclopent-1-enyl) picolinic acid, is characterized by liquid chromatography (LC) with mass spectrometry (MS) and NMR. LC-MSn experiments using electrospray ionization are used to obtain a tentative structure of the photo-degradation product from fragmentation studies, exchangeable proton analysis, and accurate mass data. H-1 LC-NMR, including nuclear Overhauser effect experiments, are performed in stopped-flow mode to confirm the structure. A small amount of material was isolated via preparative chromatography for 2D C-13 NMR analysis. The H-1 and C-13 NMR shifts of the photo-degradation product are calculated and compared to experimental values using density functional theory (DFT) to confirm the structural assignment. Several interesting features of the MS fragmentation of the photo-degradation product are examined and explained using DFT methods, including the transition state of an intramolecular Smiles rearrangement. The UV-Visible (UV-Vis) spectrum of the photo-degradation product is also predicted using time-dependent DFT (TDDFT) and matched to experimental data. A mechanism for the formation of this unusual photo-degradation product via electrocyclization is proposed and discussed. The combination of LC-MS, LC-NMR, and computational methods are used to provide a thorough structural identification of the photo-degradation product and also fully interpret the observed NMR, UV-Vis, and MS spectra. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.09.036