9-Bromodecanoic Acid | 134781-66-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9-Bromodecanoic Acid
• 英文别名: 9-Bromo-decanoic acid
• CAS: 134781-66-1
• 化学式: C₁₀H₁₉BrO₂
• 分子量: 251.164
• InChiKey: NALSZVIUTARYSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-Bromodecanoic Acid 在 sodium azide 、 四丁基溴化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.0h， 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
• 作为产物：
  描述：

  10-溴癸酸 在 氢氧化钾 、 sodium tetrahydroborate 、 2-硝基苯基丝氰酸酯 、 氢溴酸 、 双氧水 、 甲基三辛基氯化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 52.75h， 生成 9-Bromodecanoic Acid
  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

文献信息

• Silver carboxylate promoted lactonization: a general method applicable to prepare medium and large-sized lactones without high dilution or slow addition
  作者：Le Liu、Shimin Xu、Hongwei Zhou

  DOI：10.1016/j.tet.2013.07.064

  日期：2013.9

  and simple operation, remains a challenging task for the organic community. We developed a ‘freshman-can-do’ protocol to medium- and large-sized lactones, not depending on high-dilution or slow addition techniques. Application of this method for the synthesis of natural lactones or potentially pharmaceutical compounds might be useful for organic chemists and pharmacists.

  对于有机内酯而言，有效且适用的宏观内酯化方法以及充足的起始原料和简单的操作方法仍然是一项艰巨的任务。我们为中型和大型内酯开发了“新鲜人可以做”的实验方案，而不依赖于高稀释或慢速添加技术。该方法用于天然内酯或潜在药物化合物的合成对于有机化学家和药剂师可能是有用的。
• Covalent Inhibition of Bacterial Quorum Sensing
  申请人：Meijler Michael M.

  公开号：US20120135925A1

  公开（公告）日：2012-05-31

  Inhibitors of bacterial communication, such as quorum sensing, and method of use and manufacture thereof.

  细菌通讯抑制剂，例如群体感应，以及其使用和制造方法。
• Covalent inhibition of bacterial quorum sensing
  申请人：Meijler Michael M

  公开号：US08501969B2

  公开（公告）日：2013-08-06

  Inhibitors of bacterial communication, such as quorum sensing, and method of use and manufacture thereof.

  细菌通讯抑制剂，如群体感应，以及使用和制造方法。
• Granata, Alessandro; Perlin, Arthur S., Canadian Journal of Chemistry, 1993, vol. 71, # 6, p. 864 - 871
  作者：Granata, Alessandro、Perlin, Arthur S.

  DOI：——

  日期：——
• N-((S)-2-Oxo-tetrahydro-furan-3-yl)-amide derivatives as inhibitors of the bacterial quorum sensing for treating plant or animal diseases and for preventing the formation of biofilms on medical devices
  申请人：The National Institute for Biotechnology in the Negev Ltd.

  公开号：EP2448930B1

  公开（公告）日：2017-02-15