Acetic acid (S)-1-{(2R,5R)-5-[(R)-1-acetoxy-6-(4-butyl-phenoxy)-hexyl]-tetrahydro-furan-2-yl}-6-(4-butyl-phenoxy)-hexyl ester | 954371-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Acetic acid (S)-1-{(2R,5R)-5-[(R)-1-acetoxy-6-(4-butyl-phenoxy)-hexyl]-tetrahydro-furan-2-yl}-6-(4-butyl-phenoxy)-hexyl ester
• CAS: 954371-78-9
• 化学式: C₄₀H₆₀O₇
• 分子量: 652.912
• InChiKey: XLSHVBONXYZWHU-KKOUMEGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.36
• 重原子数：
  47.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (S)-1-{(2R,5R)-5-[(R)-1-acetoxy-6-(4-butyl-phenoxy)-hexyl]-tetrahydro-furan-2-yl}-6-(4-butyl-phenoxy)-hexyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(2R,5R)-2-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-tetrahydrofuran
  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 palladium on activated charcoal 、 palladium hydroxide - carbon 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 草酰氯 、 偶氮二甲酸二异丙酯 、 4 A molecular sieve 、 potassium tert-butylate 、 四丁基氟化铵 、 氢气 、 四氯化锡 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 107.5h， 生成 Acetic acid (S)-1-{(2R,5R)-5-[(R)-1-acetoxy-6-(4-butyl-phenoxy)-hexyl]-tetrahydro-furan-2-yl}-6-(4-butyl-phenoxy)-hexyl ester
  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