(2S,5R)-5-[(1R)-1-acetyloxy-6-(4-butylphenyloxy)hexyl]tetrahydrofuran-2-carbaldehyde | 926030-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,5R)-5-[(1R)-1-acetyloxy-6-(4-butylphenyloxy)hexyl]tetrahydrofuran-2-carbaldehyde
• CAS: 926030-08-2
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: HQHUZGORNDCVSF-YTFSRNRJSA-N

物化性质

• 沸点：
  519.8±50.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  28.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,5R)-5-[(1R)-1-acetyloxy-6-(4-butylphenyloxy)hexyl]tetrahydrofuran-2-carbaldehyde 在 4 A molecular sieve 、 四氯化锡 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 (2S,2'S,5R,5'R)-5,5'-bis[(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
• 作为产物：
  描述：

  5-benzyloxymethyl-2-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-3-(dimethylphenylsilyl)tetrahydrofuran 在 palladium hydroxide - carbon 4-二甲氨基吡啶 、 草酰氯 、 四丁基氟化铵 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 (2S,5R)-5-[(1R)-1-acetyloxy-6-(4-butylphenyloxy)hexyl]tetrahydrofuran-2-carbaldehyde
  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