(S)-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-5H-furan-2-one | 474650-01-6

• 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: (S)-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-5H-furan-2-one
• 英文别名: (2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyethyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
• CAS: 474650-01-6
• 化学式: C₂₈H₄₈O₆
• 分子量: 480.686
• InChiKey: CEORVEGGKXSUQT-NZSLWZAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Toluene-4-sulfonic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-ethyl ester 在 Wilkinson's catalyst bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 69.75h， 生成 (S)-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-5H-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

文献信息

• Essential structural factors of acetogenins, potent inhibitors of mitochondrial complex I
  作者：Tomoko Motoyama、Hiromi Yabunaka、Hideto Miyoshi

  DOI：10.1016/s0960-894x(02)00374-8

  日期：2002.8

  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.