1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl-3-heptanol | 371114-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl-3-heptanol
• 英文别名: 1-(2-Benzylselanyl-5-methoxyphenyl)-3-methylheptan-3-ol
• CAS: 371114-89-5
• 化学式: C₂₂H₃₀O₂Se
• 分子量: 405.439
• InChiKey: WLSCPPKJWBLYNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl-3-heptanol 在 4-二甲氨基吡啶 、 2-mercaptopyridine-1-oxide sodium salt 作用下， 以 苯 为溶剂， 反应 20.5h， 生成 2-butyl-6-methoxy-2-methylselenochromane
  参考文献：
  名称：

  Intramolecular Homolytic Substitution at Selenium:  Synthesis of Novel Selenium-Containing Vitamin E Analogues

  摘要：

  Treatment of 1-(benzylselenenyl)-5-butyl-5-nonanoI (10) with oxalyl chloride followed by the sodium salt of N-hydroxypyridine-2-thione afforded the corresponding pyridine-2-thione-N-oxycarbonyI (PTOC) oxalate ester which was not isolated but immediately heated to provide 2,2-dibutylselenane (7). This transformation presumably involves a tertiary alkyl radical that undergoes intramolecular homolytic substitution at selenium with loss of the benzyl radical to provide the selenium-containing ring system (7). A similar protocol, when applied to 1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl3-heptanol (18) and 1-(2-benzylselenenyl-5-methoxyphenyl)-3,7,11,15-tetramethyl-3-hexadecanoI (19), followed by deprotection, afforded the selenium-containing alpha -tocopherol analogues 4 and 1f, respectively, in moderate yields. To the best of our knowledge, these transformations represent the first examples of tertiary radicals involved in homolytic substitution chemistry at selenium.td2

  DOI：

  10.1021/jo010274k
• 作为产物：
  描述：

  4-(2-bromo-5-methoxyphenyl)-2-butanone 在 盐酸 、 叔丁基锂 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 42.0h， 生成 1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl-3-heptanol
  参考文献：
  名称：

  Intramolecular Homolytic Substitution at Selenium:  Synthesis of Novel Selenium-Containing Vitamin E Analogues

  摘要：

  Treatment of 1-(benzylselenenyl)-5-butyl-5-nonanoI (10) with oxalyl chloride followed by the sodium salt of N-hydroxypyridine-2-thione afforded the corresponding pyridine-2-thione-N-oxycarbonyI (PTOC) oxalate ester which was not isolated but immediately heated to provide 2,2-dibutylselenane (7). This transformation presumably involves a tertiary alkyl radical that undergoes intramolecular homolytic substitution at selenium with loss of the benzyl radical to provide the selenium-containing ring system (7). A similar protocol, when applied to 1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl3-heptanol (18) and 1-(2-benzylselenenyl-5-methoxyphenyl)-3,7,11,15-tetramethyl-3-hexadecanoI (19), followed by deprotection, afforded the selenium-containing alpha -tocopherol analogues 4 and 1f, respectively, in moderate yields. To the best of our knowledge, these transformations represent the first examples of tertiary radicals involved in homolytic substitution chemistry at selenium.td2

  DOI：

  10.1021/jo010274k

文献信息

• Intramolecular Homolytic Substitution at Selenium:  Synthesis of Novel Selenium-Containing Vitamin E Analogues
  作者：Nawaf Al-Maharik、Lars Engman、Jonas Malmström、Carl H. Schiesser

  DOI：10.1021/jo010274k

  日期：2001.9.1

  Treatment of 1-(benzylselenenyl)-5-butyl-5-nonanoI (10) with oxalyl chloride followed by the sodium salt of N-hydroxypyridine-2-thione afforded the corresponding pyridine-2-thione-N-oxycarbonyI (PTOC) oxalate ester which was not isolated but immediately heated to provide 2,2-dibutylselenane (7). This transformation presumably involves a tertiary alkyl radical that undergoes intramolecular homolytic substitution at selenium with loss of the benzyl radical to provide the selenium-containing ring system (7). A similar protocol, when applied to 1-(2-benzylselenenyl-5-methoxyphenyl)-3-methyl3-heptanol (18) and 1-(2-benzylselenenyl-5-methoxyphenyl)-3,7,11,15-tetramethyl-3-hexadecanoI (19), followed by deprotection, afforded the selenium-containing alpha -tocopherol analogues 4 and 1f, respectively, in moderate yields. To the best of our knowledge, these transformations represent the first examples of tertiary radicals involved in homolytic substitution chemistry at selenium.td2