9H-Fluoren-9-one, 2,7-diethoxy- | 303735-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-Fluoren-9-one, 2,7-diethoxy-
• 英文别名: 2,7-diethoxyfluoren-9-one
• CAS: 303735-64-0
• 化学式: C₁₇H₁₆O₃
• mdl: MFCD00427827
• 分子量: 268.312
• InChiKey: POVCQXIJGRFGTF-UHFFFAOYSA-N

物化性质

• 沸点：
  450.9±38.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9H-Fluoren-9-one, 2,7-diethoxy- 在 platinum(IV) oxide 4-二甲氨基吡啶 、 氯仿 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 0.25h， 生成 N-[2-(2,7-diethoxy-9H-fluoren-9-yl)ethyl]propanamide
  参考文献：
  名称：

  Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]-propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides

  摘要：

  A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.002
• 作为产物：
  描述：

  2-溴-5-乙氧基苯甲酸甲酯 在 tris-(dibenzylideneacetone)dipalladium(0) sodium hydroxide 、 氯化亚砜 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 生成 9H-Fluoren-9-one, 2,7-diethoxy-
  参考文献：
  名称：

  Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]-propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides

  摘要：

  A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.002

文献信息

• ——
  作者：A. V. Ivanov、S. A. Lyakhov、M. Yu. Yarkova、A. I. Galatina、A. V. Mazepa

  DOI：10.1023/a:1021686115034

  日期：——

  2,7-Dihydroxy-9-fluorenone was alkylated with alkyl halides in acetone in the presence of potassium carbonate to prepare 2,7-dialkoxy-9-fluorenones prone to mesomorphism. Mesomorphic properties are characteristic of the compounds containing in the alkoxyl chain from 5 to 14 carbon atoms. When slowly cooled, such compounds tend to vitrify in the liquid crystal phase.
• Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]-propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides
  作者：James R. Epperson、Marc A. Bruce、John D. Catt、Jeffrey A. Deskus、Donald B. Hodges、George N. Karageorge、Daniel J. Keavy、Cathy D. Mahle、Ronald J. Mattson、Astrid A. Ortiz、Michael F. Parker、Katherine S. Takaki、Brett T. Watson、Joseph P.Yevich

  DOI：10.1016/j.bmc.2004.07.002

  日期：2004.9

  A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery. (C) 2004 Elsevier Ltd. All rights reserved.