(2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran | 926029-81-4

• 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: (2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran
• 英文别名: (1R)-6-(4-butylphenoxy)-1-[(2R,5S)-5-[(2R,5S)-5-[(1S)-6-(4-butylphenoxy)-1-hydroxyhexyl]oxolan-2-yl]oxolan-2-yl]hexan-1-ol
• CAS: 926029-81-4
• 化学式: C₄₀H₆₂O₆
• 分子量: 638.929
• InChiKey: FFNQUATXYMFTMP-GMYCQMKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  46
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 对硝基苯甲酸 、 potassium carbonate 作用下， 以 甲苯 、 甲醇 为溶剂， 反应 3.5h， 以23%的产率得到(2R,2'S,5S,5'R)-5-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran
  参考文献：
  名称：

  Effect of stereochemistry of Δlac-acetogenins on the inhibition of mitochondrial complex I (NADH-ubiquinone oxidoreductase)

  摘要：

  Delta lac-Acetogenins are a new type of inhibitors of bovine heart mitochondrial complex I (NADH-ubiquinone oxidoreductase). We synthesized a series of Delta lac-acetogenins in which the stereochemistry around the hydroxylated tetrahydrofuran (THF) ring moiety was systematically modified, and examined their inhibitory effect on complex I. The present results revealed that the inhibitory effects of the bis-THF ring analogs are much more potent than those of the mono-THF ring analogs and that the stereochemistry around the bis-THF ring moiety significantly influences the inhibitory effect. The profiles of the structure-activity relationship observed for Delta lac-acetogenins were entirely different from those for natural-type acetogenins. (c) 2006 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2006.11.057
• 作为产物：
  描述：

  1-己醇,6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]- 在 咪唑 、 正丁基锂 、 草酰氯 、 偶氮二甲酸二异丙酯 、 4 A molecular sieve 、 三氟化硼乙醚 、 potassium tert-butylate 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 生成 (2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran
  参考文献：
  名称：

  Effect of stereochemistry of Δlac-acetogenins on the inhibition of mitochondrial complex I (NADH-ubiquinone oxidoreductase)

  摘要：

  Delta lac-Acetogenins are a new type of inhibitors of bovine heart mitochondrial complex I (NADH-ubiquinone oxidoreductase). We synthesized a series of Delta lac-acetogenins in which the stereochemistry around the hydroxylated tetrahydrofuran (THF) ring moiety was systematically modified, and examined their inhibitory effect on complex I. The present results revealed that the inhibitory effects of the bis-THF ring analogs are much more potent than those of the mono-THF ring analogs and that the stereochemistry around the bis-THF ring moiety significantly influences the inhibitory effect. The profiles of the structure-activity relationship observed for Delta lac-acetogenins were entirely different from those for natural-type acetogenins. (c) 2006 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2006.11.057