| 1592950-66-7

• 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: 1592950-66-7
• 化学式: C₂₃H₁₉BrF₂N₂O
• 分子量: 457.317
• InChiKey: YWVOGQFJIRMRFD-LHSJRXKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.34
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-氟苯胺 在 吡啶 、 T406石油添加剂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 96.0h， 生成 、
  参考文献：
  名称：

  Structural requirement and stereospecificity of tetrahydroquinolines as potent ecdysone agonists

  摘要：

  Tetrahydroquinoline (THQ)- type compounds are a class of potential larvicides against mosquitoes. The structure-activity relationships (SAR) of these compounds were previously investigated (Smith et al., Bioorg. Med. Chem. Lett. 2003, 13, 1943-1946), and one of cis-forms (with respect to the configurations of 2-methyl and 4-anilino substitutions on the THQ basic structure) was stereoselectively synthesized. However, the absolute configurations of C2 and C4 were not determined. In this study, four THQ-type compounds with cis configurations were synthesized, and two were submitted for X-ray crystal structure analysis. This analysis demonstrated that two enantiomers are packed into the crystal form. We synthesized the cis-form of the fluorinated THQ compound, according to the published method, and the enantiomers were separated via chiral HPLC. The absolute configurations of the enantiomers were determined by X-ray crystallography. Each of the enantiomers was tested for activity against mosquito larvae in vivo and competitive binding to the ecdysone receptor in vitro. Compared to the (2S, 4R) enantiomer, the (2R, 4S) enantiomer showed 55 times higher activity in the mosquito larvicidal assay, and 36 times higher activity in the competitive receptor binding assay. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.043