(R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol | 676352-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol
• CAS: 676352-04-8
• 化学式: C₂₅H₄₄O₅
• 分子量: 424.621
• InChiKey: HYZLHNLWJUDYOE-VRVGQERDSA-N

物化性质

• 沸点：
  533.2±35.0 °C(predicted)
• 密度：
  1.028±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol 在 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 sodium acetate 、 三乙胺 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 Imidazole-1-carbothioic acid O-[(R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-13-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-tridecyl] ester
  参考文献：
  名称：

  Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings

  摘要：

  The presence of two hydroxy groups adjacent to the THF ring(s) is a common structural feature of natural acetogenins. To elucidate the role of each hydroxy group in the inhibitory action of acetogenins, we synthesized three acetogenin analogues which lack either or both of the hydroxy groups, and investigated their inhibitory activities with bovine heart mitochondrial complex I. Our results indicate that the presence of either of the two hydroxy groups sufficiently sustains a potent inhibitory effect. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.021
• 作为产物：
  描述：

  (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-4-trimethylsilanyl-but-3-yn-1-ol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol
  参考文献：
  名称：

  Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings

  摘要：

  The presence of two hydroxy groups adjacent to the THF ring(s) is a common structural feature of natural acetogenins. To elucidate the role of each hydroxy group in the inhibitory action of acetogenins, we synthesized three acetogenin analogues which lack either or both of the hydroxy groups, and investigated their inhibitory activities with bovine heart mitochondrial complex I. Our results indicate that the presence of either of the two hydroxy groups sufficiently sustains a potent inhibitory effect. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.021