(2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(2R,5S)-5-undecyloxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one | 676351-93-2

• 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: (2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(2R,5S)-5-undecyloxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
• CAS: 676351-93-2
• 化学式: C₃₇H₆₆O₅
• 分子量: 590.928
• InChiKey: HTKRHXGPOODCSB-CXPQHEJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  42
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(2R,5S)-5-undecyloxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (2S)-2-methyl-4-[13-[(2S,5R)-5-[(2R,5S)-5-undecyloxolan-2-yl]oxolan-2-yl]tridecyl]-2H-furan-5-one
  参考文献：
  名称：

  Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2003.11.021
• 作为产物：
  描述：

  1-壬炔 在 palladium on activated charcoal 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 偶氮二异丁腈 、 三甲基溴硅烷 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 三正丁基氢锡 、 sodium acetate 、 potassium carbonate 、 三乙胺 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 13.75h， 生成 (2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(2R,5S)-5-undecyloxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
  参考文献：
  名称：

  Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2003.11.021

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.