(R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol | 474650-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol
• CAS: 474650-08-3
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: LDCIQYPAHKXGPC-FAYOZSNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol 在 Wilkinson's catalyst bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 48.5h， 生成 (S)-3-Benzenesulfinyl-3-{(R)-13-hydroxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-dihydro-furan-2-one
  参考文献：
  名称：

  Essential structural factors of acetogenins, potent inhibitors of mitochondrial complex I

  摘要：

  To elucidate the role of the hydrophobic alkyl tail of acetogenins in the inhibitory action, we synthesized an acetogenin derivative possessing the shortest tail (i.e., methyl group) and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicated that the alkyl tail, which is one of the common structural features of natural acetogenins, is not an essential structural factor required for the potent inhibition. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00374-8
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2R,5R,2'R,5'R)-(R)-5'-oxiranyl-octahydro-[2,2']bifuranyl-5-yl)-ethyl ester 在 palladium on activated charcoal 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 117.25h， 生成 (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol
  参考文献：
  名称：

  Essential structural factors of acetogenins, potent inhibitors of mitochondrial complex I

  摘要：

  To elucidate the role of the hydrophobic alkyl tail of acetogenins in the inhibitory action, we synthesized an acetogenin derivative possessing the shortest tail (i.e., methyl group) and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicated that the alkyl tail, which is one of the common structural features of natural acetogenins, is not an essential structural factor required for the potent inhibition. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00374-8