(5Z,8Z,11Z,14Z)-19-azidoeicosa-5,8,11,14-tetraenoic acid | 742078-70-2

• 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: (5Z,8Z,11Z,14Z)-19-azidoeicosa-5,8,11,14-tetraenoic acid
• 英文别名: (5Z,8Z,11Z,14Z)-19-azidoicosa-5,8,11,14-tetraenoic acid
• CAS: 742078-70-2
• 化学式: C₂₀H₃₁N₃O₂
• 分子量: 345.485
• InChiKey: DBFIISOTSLXNEV-TWVHMNNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 5-(trimethylsilyl)-4-pentynyl ketone 在 Lindlar's catalyst 吡啶 、 喹啉 、 sodium hydroxide 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 sodium azide 、 四溴化碳 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 67.0h， 生成 (5Z,8Z,11Z,14Z)-19-azidoeicosa-5,8,11,14-tetraenoic acid
  参考文献：
  名称：

  Synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues through a common synthetic route

  摘要：

  Total synthesis of (5Z,8Z, 11Z, 14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-H-3(8)]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.02.008

文献信息

• Synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues through a common synthetic route
  作者：Stepan G. Romanov、Igor V. Ivanov、Valery P. Shevchenko、Igor Yu. Nagaev、Alexandr A. Pushkov、Nikolai F. Myasoedov、Galina I. Myagkova、Hartmut Kuhn

  DOI：10.1016/j.chemphyslip.2004.02.008

  日期：2004.7

  Total synthesis of (5Z,8Z, 11Z, 14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-H-3(8)]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis. (C) 2004 Elsevier Ireland Ltd. All rights reserved.