methyl 4-((3R,7R,11R)-3-(benzyloxy)-3,7,11,15-tetramethylhexadec-1-yn-1-yl)-1,6-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate | 1257984-28-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 4-((3R,7R,11R)-3-(benzyloxy)-3,7,11,15-tetramethylhexadec-1-yn-1-yl)-1,6-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate
• CAS: 1257984-28-3
• 化学式: C₃₈H₅₆N₂O₃
• 分子量: 588.874
• InChiKey: RQOOEUNFCARWMZ-QQJQPJPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.94
• 重原子数：
  43.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  51.66
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl 1,6-dimethyl-4-(trifluoromethylsulfonyloxy)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate 、 3-benzoxy-(3R,7R,11R)-3,7,11,15-tetramethylhexadec-1-yne 在 copper(l) iodide 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以95%的产率得到methyl 4-((3R,7R,11R)-3-(benzyloxy)-3,7,11,15-tetramethylhexadec-1-yn-1-yl)-1,6-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate
  参考文献：
  名称：

  Design, synthesis, and evaluation of an α-tocopherol analogue as a mitochondrial antioxidant

  摘要：

  An efficient synthesis has provided access to a novel alpha-tocopherol analogue (2), as well as its trifluoroacetate salt and acetate ester. An annulation reaction was used to establish the pyridinol core structure and a Stille coupling reaction was employed for conjugation with the tocopherol side chain. This analogue was shown to suppress the levels of reactive oxygen species in cultured cells, and to quench peroxidation of mitochondrial membranes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.030