1-[5'-(1-hydroxy-5-propyl-oct-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-5-propyl-oct-3-yn-1-ol | 900865-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 1-[5'-(1-hydroxy-5-propyl-oct-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-5-propyl-oct-3-yn-1-ol
• CAS: 900865-47-6
• 化学式: C₃₀H₅₀O₄
• 分子量: 474.725
• InChiKey: WWWHARBVHUZWND-VHNXJUCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[5'-(1-hydroxy-5-propyl-oct-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-5-propyl-oct-3-yn-1-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (1R)-1-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxy-5-propyloctyl]oxolan-2-yl]oxolan-2-yl]-5-propyloctan-1-ol
  参考文献：
  名称：

  Function of the alkyl side chains of Δlac-acetogenins in the inhibitory effect on mitochondrial complex I (NADH-ubiquinone oxidoreductase)

  摘要：

  We synthesized a series of Alac-acetogenins in which the two alkyl side chains were systematically modified, and examined their inhibitory effect on bovine heart mitochondrial complex I (NADH-ubiquinone oxidoreductase). The results revealed that the physicochemical properties of the side chains, such as the balance of hydrophobicity and the width (or bulkiness) of the chains, are important structural factors for a potent inhibitory effect of amphiphilic Alac-acetogenins. This is probably because such properties decide the precise location of the hydrophilic bis-THF ring moiety in the enzyme embedded in the inner mitochondrial membrane. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.082
• 作为产物：
  描述：

  2-丙基戊醛 在 4-二甲氨基吡啶 、 正丁基锂 、 二甲基硫 、 三氟化硼乙醚 、 氯化二乙基铝 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 1-[5'-(1-hydroxy-5-propyl-oct-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-5-propyl-oct-3-yn-1-ol
  参考文献：
  名称：

  Function of the alkyl side chains of Δlac-acetogenins in the inhibitory effect on mitochondrial complex I (NADH-ubiquinone oxidoreductase)

  摘要：

  We synthesized a series of Alac-acetogenins in which the two alkyl side chains were systematically modified, and examined their inhibitory effect on bovine heart mitochondrial complex I (NADH-ubiquinone oxidoreductase). The results revealed that the physicochemical properties of the side chains, such as the balance of hydrophobicity and the width (or bulkiness) of the chains, are important structural factors for a potent inhibitory effect of amphiphilic Alac-acetogenins. This is probably because such properties decide the precise location of the hydrophilic bis-THF ring moiety in the enzyme embedded in the inner mitochondrial membrane. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.082