1-(2-tert-butyldimethylsilyloxynaphthalen-1-yl)-3-(2-methylphenyl)-3-(4-methylpiperazin-1-yl)-2-propen-1-one | 1219684-06-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 1-(2-tert-butyldimethylsilyloxynaphthalen-1-yl)-3-(2-methylphenyl)-3-(4-methylpiperazin-1-yl)-2-propen-1-one
• CAS: 1219684-06-6
• 化学式: C₃₁H₄₀N₂O₂Si
• 分子量: 500.756
• InChiKey: NYAWPHUHJLSNTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-tert-butyldimethylsilyloxynaphthalen-1-yl)-3-(2-methylphenyl)-3-(4-methylpiperazin-1-yl)-2-propen-1-one 在 水 作用下， 以 二甲基亚砜 为溶剂， 反应 9.5h， 以84%的产率得到1-(2-hydroxynaphthalen-1-yl)-3-(2-methylphenyl)-3-(4-methylpiperazin-1-yl)-2-propen-1-one
  参考文献：
  名称：

  β-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: Improvement of solubility by disruption of molecular planarity

  摘要：

  The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical modification of an AhR agonist, beta-naphthoflavone, focusing on planarity-disruption. As expected, introduction of substituents at the ortho-positions of the phenyl group resulted in greater solubility. Among the compounds prepared, the fluoro analog showed more potent AhR agonistic activity and greater solubility than did b-naphthoflavone. Our results indicate that this strategy to improve aqueous solubility, that is, introduction of substituent(s) that disrupt planarity, may be generally applicable to bicyclic molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.036
• 作为产物：
  描述：

  N-甲基哌嗪 、 1-(2-tert-butyldimethylsilyloxynaphthalen-1-yl)-3-(2-methylphenyl)-2-propyn-1-one 在 乙醇 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以58%的产率得到1-(2-tert-butyldimethylsilyloxynaphthalen-1-yl)-3-(2-methylphenyl)-3-(4-methylpiperazin-1-yl)-2-propen-1-one
  参考文献：
  名称：

  β-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: Improvement of solubility by disruption of molecular planarity

  摘要：

  The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical modification of an AhR agonist, beta-naphthoflavone, focusing on planarity-disruption. As expected, introduction of substituents at the ortho-positions of the phenyl group resulted in greater solubility. Among the compounds prepared, the fluoro analog showed more potent AhR agonistic activity and greater solubility than did b-naphthoflavone. Our results indicate that this strategy to improve aqueous solubility, that is, introduction of substituent(s) that disrupt planarity, may be generally applicable to bicyclic molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.036