(S)-3-((E)-(13R,14R,17S,18S)-13-Hydroxy-14,17,18-tris-methoxymethoxy-triacont-8-en-10-ynyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one | 676441-72-8

• 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: (S)-3-((E)-(13R,14R,17S,18S)-13-Hydroxy-14,17,18-tris-methoxymethoxy-triacont-8-en-10-ynyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one
• CAS: 676441-72-8
• 化学式: C₄₇H₇₈O₉S
• 分子量: 819.197
• InChiKey: VGJVPCYSVVHYSP-BHYOWQNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.95
• 重原子数：
  57.0
• 可旋转键数：
  36.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((E)-(13R,14R,17S,18S)-13-Hydroxy-14,17,18-tris-methoxymethoxy-triacont-8-en-10-ynyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 在 Wilkinson's catalyst 、 氢气 作用下， 以 苯 为溶剂， 以97%的产率得到(S)-3-((13R,14R,17S,18S)-13-Hydroxy-14,17,18-tris-methoxymethoxy-triacontyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis and mitochondrial complex I inhibition of dihydroxy-cohibin A, non-THF annonaceous acetogenin analogue

  摘要：

  To elucidate the inhibitory action of acetogenins, we synthesized an acetogenin derivative which possesses tetraol in place of the tetrahydrofuran ring and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicate that these hydroxy groups are an essential structural factor though it is not effective as bis-THF hydroxy groups combination. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.057
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (2R,3R,6S,7S)-2,3,6-tris-(2-ethoxy-ethoxy)-7-methoxymethoxy-nonadecyl ester 在 四氢吡咯 、 potassium fluoride 、 氢氧化钾 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 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， 生成 (S)-3-((E)-(13R,14R,17S,18S)-13-Hydroxy-14,17,18-tris-methoxymethoxy-triacont-8-en-10-ynyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis and mitochondrial complex I inhibition of dihydroxy-cohibin A, non-THF annonaceous acetogenin analogue

  摘要：

  To elucidate the inhibitory action of acetogenins, we synthesized an acetogenin derivative which possesses tetraol in place of the tetrahydrofuran ring and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicate that these hydroxy groups are an essential structural factor though it is not effective as bis-THF hydroxy groups combination. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.057