Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester | 900865-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester
• CAS: 900865-45-4
• 化学式: C₃₁H₅₆O₈SSi₂
• 分子量: 645.018
• InChiKey: VMPVBFWLHLLGDM-CJAVQSORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester 在 4-二甲氨基吡啶 、 氢氧化钾 、 正丁基锂 、 二甲基硫 、 三氟化硼乙醚 、 四丁基氟化铵 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.75h， 生成 (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-4-trimethylsilanyl-but-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-undec-3-yn-1-ol
  参考文献：
  名称：

  Synthesis and inhibitory activity of ubiquinone–acetogenin hybrid inhibitor with bovine mitochondrial complex I

  摘要：

  To elucidate the inhibitory action of acetogenins, the most potent inhibitors of mitochondrial complex I, we synthesized an acetogenin analogue which possesses a ubiquinone ring (i.e., the physiological substrate of complex I) in place of the alpha,beta-unsaturated gamma-lactone ring of natural acetogenins, and named it Q-acetogenin. Our results indicate that the gamma-lactone ring of acetogenins is completely substitutable with the ubiquinone ring. This fact is discussed in light of the inhibitory action of acetogenins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00439-6
• 作为产物：
  描述：

  对甲苯磺酰氯 、 (S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethanol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以55%的产率得到Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester
  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