11,14,17-Eicosatrienoic acid, DMOX derivative | 944031-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 11,14,17-Eicosatrienoic acid, DMOX derivative
• 英文别名: 4,4-dimethyl-2-[(10Z,13Z,16Z)-nonadeca-10,13,16-trienyl]-5H-1,3-oxazole
• CAS: 944031-10-1
• 化学式: C₂₄H₄₁NO
• 分子量: 359.596
• InChiKey: ILKIQQUKRCSUSF-AGRJPVHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11,14,17-Eicosatrienoic acid, DMOX derivative 在 氢氧化钾 、 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 顺式-11,14,17-二十碳三烯酸
  参考文献：
  名称：

  Chemical C2-elongation of polyunsaturated fatty acids

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2006.09.002
• 作为产物：
  描述：

  亚麻酸甲酯 在 lithium aluminium tetrahydride 、 正丁基锂 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.58h， 生成 11,14,17-Eicosatrienoic acid, DMOX derivative
  参考文献：
  名称：

  Chemical C2-elongation of polyunsaturated fatty acids

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2006.09.002

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.