1-(1,3-dithian-2-yl)-2-(4-isobutylphenyl)-propan-1-one | 1246302-55-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(1,3-dithian-2-yl)-2-(4-isobutylphenyl)-propan-1-one
• 英文别名: 1-(1,3-Dithian-2-yl)-2-[4-(2-methylpropyl)phenyl]propan-1-one
• CAS: 1246302-55-5
• 化学式: C₁₇H₂₄OS₂
• 分子量: 308.509
• InChiKey: MMUMATXYXOEJGR-UHFFFAOYSA-N

物化性质

• 沸点：
  436.6±45.0 °C(predicted)
• 密度：
  1.098±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二噻烷 、 2-(4-isobutylphenyl)-N-methoxy-N-methylpropanamide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以57%的产率得到1-(1,3-dithian-2-yl)-2-(4-isobutylphenyl)-propan-1-one
  参考文献：
  名称：

  Chemistry around imidazopyrazine and ibuprofen: Discovery of novel fatty acid amide hydrolase (FAAH) inhibitors

  摘要：

  Based on the imidazo-[1,2-a]-pyrazin-3-(7H)-one scaffold, a dual action prodrug has been designed for combining antioxidant and anti-inflammatory activities, possibly unmasked upon oxidation. The construction of the target-molecule requires two building blocks, namely a 2-amino-1,4-pyrazine and a 2-ketoaldehyde. Attempts to synthesize the 2-ketoaldehyde (5a) derived from ibuprofen failed, but led to the corresponding 2-ketoaldoxime (7a) which could not be condensed with the pyrazine synthons. However, a model compound, i.e. phenylglyoxal aldoxime, reacted well under microwave activation to furnish novel imidazo[1,2-a]-pyrazine-3-(7H)-imine derivatives (18a,b). These heterobicycles behave as antioxidants by inhibiting the lipid peroxidation, and one compound (18b) is endowed with a significant anti-inflammatory effect in a cellular test. Unexpectedly, all the synthetic intermediates derived from ibuprofen are good inhibitors of FAAH, the most active compound (4a) featuring the 1,3-dithian-2-yl motif. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.040

文献信息

• Chemistry around imidazopyrazine and ibuprofen: Discovery of novel fatty acid amide hydrolase (FAAH) inhibitors
  作者：Frédéric De Wael、Giulio G. Muccioli、Didier M. Lambert、Thérèse Sergent、Yves-Jacques Schneider、Jean-François Rees、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.ejmech.2010.04.040

  日期：2010.9

  Based on the imidazo-[1,2-a]-pyrazin-3-(7H)-one scaffold, a dual action prodrug has been designed for combining antioxidant and anti-inflammatory activities, possibly unmasked upon oxidation. The construction of the target-molecule requires two building blocks, namely a 2-amino-1,4-pyrazine and a 2-ketoaldehyde. Attempts to synthesize the 2-ketoaldehyde (5a) derived from ibuprofen failed, but led to the corresponding 2-ketoaldoxime (7a) which could not be condensed with the pyrazine synthons. However, a model compound, i.e. phenylglyoxal aldoxime, reacted well under microwave activation to furnish novel imidazo[1,2-a]-pyrazine-3-(7H)-imine derivatives (18a,b). These heterobicycles behave as antioxidants by inhibiting the lipid peroxidation, and one compound (18b) is endowed with a significant anti-inflammatory effect in a cellular test. Unexpectedly, all the synthetic intermediates derived from ibuprofen are good inhibitors of FAAH, the most active compound (4a) featuring the 1,3-dithian-2-yl motif. (C) 2010 Elsevier Masson SAS. All rights reserved.