2-bromoeicos-1-ene | 153499-82-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-bromoeicos-1-ene
• CAS: 153499-82-2
• 化学式: C₂₀H₃₉Br
• 分子量: 359.434
• InChiKey: SKVWTHKSKPHCQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.55
• 重原子数：
  21.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2-bromoeicos-1-ene 在 六甲基磷酰三胺 、 sodium hydroxide 、 正丁基锂 、 四丁基氢氧化铵 、 十六烷基三甲基溴化铵 、 二甲基亚砜 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 12.25h， 生成 methyl 4-(2-octadecylcyclopropen-1-yl)butanoate
  参考文献：
  名称：

  The synthesis of methyl 4-(2-octadecylcyclopropen-l-yl)butanoate: a possible inhibitor in mycolic acid biosynthesis

  摘要：

  The high molecular weight 2-alkyl-3-hydroxy mycolic acids are key structural components of the cell envelope of pathogenic mycobacteria such as Mycobacterium tuberculosis. It has been shown recently that (Z)-tetracos-5-enoic acid is a key initial intermediate in mycolic acid biosynthesis in extracts of Mycobacterium smegmatis. This acid is presumably for-med by desaturation of tetracosanoate, and previous studies on oleic acid biosynthesis suggest that a cyclopropene analogue may be a potential inhibitor. This communication describes the synthesis of methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, which is shown elsewhere to be an inhibitor of the initial stages of mycolic acid synthesis.

  DOI：

  10.1016/0009-3084(93)90028-2
• 作为产物：
  描述：

  硬脂基溴 在 四乙基溴化铵 、 氢溴酸 、 乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-bromoeicos-1-ene
  参考文献：
  名称：

  The synthesis of methyl 4-(2-octadecylcyclopropen-l-yl)butanoate: a possible inhibitor in mycolic acid biosynthesis

  摘要：

  The high molecular weight 2-alkyl-3-hydroxy mycolic acids are key structural components of the cell envelope of pathogenic mycobacteria such as Mycobacterium tuberculosis. It has been shown recently that (Z)-tetracos-5-enoic acid is a key initial intermediate in mycolic acid biosynthesis in extracts of Mycobacterium smegmatis. This acid is presumably for-med by desaturation of tetracosanoate, and previous studies on oleic acid biosynthesis suggest that a cyclopropene analogue may be a potential inhibitor. This communication describes the synthesis of methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, which is shown elsewhere to be an inhibitor of the initial stages of mycolic acid synthesis.

  DOI：

  10.1016/0009-3084(93)90028-2