stearidonyl bromide | 181213-46-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: stearidonyl bromide
• 英文别名: 1-bromo-6Z,9Z,12Z,15Z-octadecatetraene
• CAS: 181213-46-7
• 化学式: C₁₈H₂₉Br
• 分子量: 325.332
• InChiKey: NANOIENDJPMXIA-LTKCOYKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  19.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  stearidonyl bromide 在 sodium hydroxide 、 sodium 作用下， 以 乙醇 、 二乙二醇二甲醚 、 水 为溶剂， 反应 7.0h， 生成 (8Z,11Z,14Z,17Z)-8,11,14,17-二十碳四烯酸
  参考文献：
  名称：

  Kuklev; Popkov; Kas'yanov, Russian Journal of Bioorganic Chemistry, 1996, vol. 22, # 3, p. 192 - 195

  摘要：

  DOI：
• 作为产物：
  描述：

  (6Z,9Z,12Z,15Z)-十八碳四烯酸甲酯 在 lithium aluminium tetrahydride 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 3.0h， 生成 stearidonyl bromide
  参考文献：
  名称：

  Kuklev; Popkov; Kas'yanov, Russian Journal of Bioorganic Chemistry, 1996, vol. 22, # 3, p. 192 - 195

  摘要：

  DOI：

文献信息

• Chemical C2-elongation of polyunsaturated fatty acids
  作者：Dmitry V. Kuklev、William L. Smith

  DOI：10.1016/j.chemphyslip.2006.09.002

  日期：2006.11

  Three fatty acids were synthesized from commercially available alpha-linolenic, stearidonic and eicosapentaenoic acids by C2-elongation using a four step preparative technique. The parent fatty acid methyl esters were reduced to alcohols with LiAlH4, converted to bromides by treatment with triphenylphosphine dibromide, coupled with a lithiated C2-elongation block -2,4,4-trimethyl-2-oxazoline - to form the corresponding 2,2-dimethyloxazolines of C2-elongated fatty acids, and finally, converted to the target polyunsaturated fatty acids by acidic alcoholysis. Yields of more than 60% were achieved on a gram scale. The resulting 11Z, 14Z, 17Z-eicosatrienoic, 8Z, 11Z, 14Z, 17Z-eicosatetraenoic and 7Z, 10Z,13Z, 16Z, 19Z-docosapentaenoic acids were obtained as colorless oils with > 98% purity and could be used for biochemical investigations without additional purification. The elongated fatty acids were free of byproducts that could result from Z-E isomerization or migration of double bonds. (c) 2006 Elsevier Ireland Ltd. All rights reserved.