stearic-1,1'-13C2 anhydride | 89088-45-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: stearic-1,1'-13C2 anhydride
• CAS: 89088-45-9
• 化学式: C₃₆H₇₀O₃
• 分子量: 552.928
• InChiKey: WVJVHUWVQNLPCR-HDBNOXJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.58
• 重原子数：
  39.0
• 可旋转键数：
  32.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-溴乙基二氯膦酸酯 、 硬脂酸 、 stearic-1,1'-13C2 anhydride 、 甘油-2-13C 、 甘油-1,3-13C2 、 三甲胺 在 三苯基氯甲烷 、 N,N-二异丙基乙胺 、 甲醇 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2,3-di-O-stearoyl-sn-glycero-3-phosphocholine-2,1',1"-13C3 、 2,3-di-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1',1"-13C4
  参考文献：
  名称：

  The total synthesis of 2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1′-13C3 and -2,1′-13C2 by a novel chemoenzymatic method

  摘要：

  2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A(2) was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydride. This phospholipid is an important biosynthetic precursor of arachidonic acid metabolites as well as the endocannabinoid 2-arachidonoylglycerol (2-AG), and is now available for NMR studies. (C) 2009 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2009.08.001
• 作为产物：
  描述：

  硬脂酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氯化碳 为溶剂， 生成 stearic-1,1'-13C2 anhydride
  参考文献：
  名称：

  The total synthesis of 2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1′-13C3 and -2,1′-13C2 by a novel chemoenzymatic method

  摘要：

  2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A(2) was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydride. This phospholipid is an important biosynthetic precursor of arachidonic acid metabolites as well as the endocannabinoid 2-arachidonoylglycerol (2-AG), and is now available for NMR studies. (C) 2009 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2009.08.001