(1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis(6-(4-(n-butyl)phenoxy)hex-3-yn-1-ol) | 839674-19-0

• 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: (1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis(6-(4-(n-butyl)phenoxy)hex-3-yn-1-ol)
• 英文别名: (1R)-6-(4-butylphenoxy)-1-[(2R,5R)-5-[(2R,5R)-5-[(1R)-6-(4-butylphenoxy)-1-hydroxyhex-3-ynyl]oxolan-2-yl]oxolan-2-yl]hex-3-yn-1-ol
• CAS: 839674-19-0
• 化学式: C₄₀H₅₄O₆
• 分子量: 630.865
• InChiKey: MDEULAGRCKIUHD-ZNAXKYJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis(6-(4-(n-butyl)phenoxy)hex-3-yn-1-ol) 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以87%的产率得到(2R,2'R,5R,5'R)-5,5'-bis[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran
  参考文献：
  名称：

  Synthesis and characterization of Δlac-acetogenins that potently inhibit mitochondrial complex I

  摘要：

  Four Dlac-acetogenins have been prepared and characterized as inhibitors of the mitochondrial respiratory chain, to define the effects of unsaturation within the alkyl substituents. In keeping with earlier reports, the presence of acetylenic functionalities within the alkyl substituents slightly diminished their potency of inhibition of NADH oxidase activity, which measures the overall transfer of electrons from NADH to oxygen through mitochondrial complexes I, III, and IV. In contrast, both of the acetylenic Dlac-acetogenins were far more active in a NADH-ubiquinone Q(1) oxidoreductase assay that measures complex I function per se. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.071
• 作为产物：
  描述：

  1-(but-3-ynyloxy)-4-(n-butyl)benzene 、 (-)-(2R,3R,6R,7R,10R,11R)-1,2:3,6:7,10:11,12-tetraepoxydodecane 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以99%的产率得到(1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis(6-(4-(n-butyl)phenoxy)hex-3-yn-1-ol)
  参考文献：
  名称：

  Synthesis and characterization of Δlac-acetogenins that potently inhibit mitochondrial complex I

  摘要：

  Four Dlac-acetogenins have been prepared and characterized as inhibitors of the mitochondrial respiratory chain, to define the effects of unsaturation within the alkyl substituents. In keeping with earlier reports, the presence of acetylenic functionalities within the alkyl substituents slightly diminished their potency of inhibition of NADH oxidase activity, which measures the overall transfer of electrons from NADH to oxygen through mitochondrial complexes I, III, and IV. In contrast, both of the acetylenic Dlac-acetogenins were far more active in a NADH-ubiquinone Q(1) oxidoreductase assay that measures complex I function per se. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.071