(R)-1-[(2R,5R,2'R,5'R)-5'-((S)-2-Hydroxy-1-methoxymethoxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-undec-3-yn-1-ol | 596828-46-5

• 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: (R)-1-[(2R,5R,2'R,5'R)-5'-((S)-2-Hydroxy-1-methoxymethoxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-undec-3-yn-1-ol
• CAS: 596828-46-5
• 化学式: C₂₃H₄₀O₆
• 分子量: 412.567
• InChiKey: PFQTVHNOEJXFPX-RCQJKQRMSA-N

物化性质

• 沸点：
  554.2±40.0 °C(predicted)
• 密度：
  1.094±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-1-[(2R,5R,2'R,5'R)-5'-((S)-2-Hydroxy-1-methoxymethoxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-undec-3-yn-1-ol 在 4-二甲氨基吡啶 、 氢氧化钾 、 二甲基硫 、 三氟化硼乙醚 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.25h， 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：

  (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 、 正丁基锂 、 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 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (R)-1-[(2R,5R,2'R,5'R)-5'-((S)-2-Hydroxy-1-methoxymethoxy-ethyl)-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

文献信息

• Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings
  作者：Masato Abe、Atsushi Kenmochi、Naoya Ichimaru、Takeshi Hamada、Takaaki Nishioka、Hideto Miyoshi

  DOI：10.1016/j.bmcl.2003.11.021

  日期：2004.2

  The presence of two hydroxy groups adjacent to the THF ring(s) is a common structural feature of natural acetogenins. To elucidate the role of each hydroxy group in the inhibitory action of acetogenins, we synthesized three acetogenin analogues which lack either or both of the hydroxy groups, and investigated their inhibitory activities with bovine heart mitochondrial complex I. Our results indicate that the presence of either of the two hydroxy groups sufficiently sustains a potent inhibitory effect. (C) 2003 Elsevier Ltd. All rights reserved.