Pentachlorophenyl 9-Azidodecanoate | 134781-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Pentachlorophenyl 9-Azidodecanoate
• 英文别名: (2,3,4,5,6-pentachlorophenyl) 9-azidodecanoate
• CAS: 134781-61-6
• 化学式: C₁₆H₁₈Cl₅N₃O₂
• 分子量: 461.603
• InChiKey: HCHAJPSUHSGQNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.06
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Pentachlorophenyl 9-Azidodecanoate 在 苯硒酚 、 tin(ll) chloride 、 1-叠氮基乙烷 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以25%的产率得到10,20-dimethyl-1,11-diazacycloicosane-2,12-dione
  参考文献：
  名称：

  Cyclization of 9-substituted decanoic acid derivatives to 9-decanolide and 9-decanolactam

  摘要：

  Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedrues for lactonization and lactamization at 80-degrees-C under identical high-dilution conditions. The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed with anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions. Analogously, treatment of S-2-pyridyl 9-azidodecanethioate with Sn(SePh)3-afforded the best yield of the 10-membered lactam. The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag+ strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.

  DOI：

  10.1021/jo00017a027
• 作为产物：
  描述：

  9-癸烯酸 在 sodium azide 、 四丁基溴化铵 、 氢溴酸 、 甲基三辛基氯化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.75h， 生成 Pentachlorophenyl 9-Azidodecanoate
  参考文献：
  名称：

  Cyclization of 9-substituted decanoic acid derivatives to 9-decanolide and 9-decanolactam

  摘要：

  Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedrues for lactonization and lactamization at 80-degrees-C under identical high-dilution conditions. The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed with anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions. Analogously, treatment of S-2-pyridyl 9-azidodecanethioate with Sn(SePh)3-afforded the best yield of the 10-membered lactam. The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag+ strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.

  DOI：

  10.1021/jo00017a027