5-Hydroxy-3-(phenylselanylmethyl)-3,4-dihydrochromen-2-one | 88703-35-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 5-Hydroxy-3-(phenylselanylmethyl)-3,4-dihydrochromen-2-one
• CAS: 88703-35-9
• 化学式: C₁₆H₁₄O₃Se
• 分子量: 333.245
• InChiKey: YAEBPZSSJAJSOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  494.4±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-3-(phenylselanylmethyl)-3,4-dihydrochromen-2-one 、 辛酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以67%的产率得到5-hydroxy-3-[(phenylseleno)methyl]hydrocoumarinoctanoate
  参考文献：
  名称：

  Synthesis and antitumor activity of some aromatic selenolactones

  摘要：

  Several aromatic seleno lactones have been synthesized and shown to possess significant inhibitory activity against human colon tumor-8r cells in culture at concentrations lower than 1 mM. Although all of the compounds tested were found to be active, 5-hydroxy-3-[(phenylseleno)methyl]hydrocoumarinoctanoate (3d) and 5-hydroxy-3-[(phenylseleno)methyl]hydrocoumarindecanoate (3e) were found to be the most effective in inhibiting cell growth. In situ formation of the corresponding alpha-methylene lactones is postulated to account for the cytotoxic activity in this class of compounds.

  DOI：

  10.1021/jm00370a022
• 作为产物：
  描述：

  3-phenylselenomethyl-5-acetoxy-3,4-dihydrocoumarin 在 甲烷磺酸 作用下， 以 甲酸 为溶剂， 反应 5.0h， 以75%的产率得到5-Hydroxy-3-(phenylselanylmethyl)-3,4-dihydrochromen-2-one
  参考文献：
  名称：

  Synthesis and antitumor activity of some aromatic selenolactones

  摘要：

  Several aromatic seleno lactones have been synthesized and shown to possess significant inhibitory activity against human colon tumor-8r cells in culture at concentrations lower than 1 mM. Although all of the compounds tested were found to be active, 5-hydroxy-3-[(phenylseleno)methyl]hydrocoumarinoctanoate (3d) and 5-hydroxy-3-[(phenylseleno)methyl]hydrocoumarindecanoate (3e) were found to be the most effective in inhibiting cell growth. In situ formation of the corresponding alpha-methylene lactones is postulated to account for the cytotoxic activity in this class of compounds.

  DOI：

  10.1021/jm00370a022

文献信息

• Synthesis and antitumor activity of some aromatic selenolactones
  作者：W. C. Groutas、M. C. Theodorakis、W. A. F. Tomkins、G. Herro、T. Gaynor

  DOI：10.1021/jm00370a022

  日期：1984.4

  Several aromatic seleno lactones have been synthesized and shown to possess significant inhibitory activity against human colon tumor-8r cells in culture at concentrations lower than 1 mM. Although all of the compounds tested were found to be active, 5-hydroxy-3-[(phenylseleno)methyl]hydrocoumarinoctanoate (3d) and 5-hydroxy-3-[(phenylseleno)methyl]hydrocoumarindecanoate (3e) were found to be the most effective in inhibiting cell growth. In situ formation of the corresponding alpha-methylene lactones is postulated to account for the cytotoxic activity in this class of compounds.