(5S,15'S,16'S)-3-(15'-hydroxy-16'-methoxymethoxyditriacontyl)-5-methyl-2,5-dihydrofuran-2-one | 937182-42-8

• 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: (5S,15'S,16'S)-3-(15'-hydroxy-16'-methoxymethoxyditriacontyl)-5-methyl-2,5-dihydrofuran-2-one
• CAS: 937182-42-8
• 化学式: C₃₉H₇₄O₅
• 分子量: 623.014
• InChiKey: JACZKBIUGSTZMR-VRQIXWKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.54
• 重原子数：
  44.0
• 可旋转键数：
  34.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5S,15'S,16'S)-3-(15'-hydroxy-16'-methoxymethoxyditriacontyl)-5-methyl-2,5-dihydrofuran-2-one 在 三氟化硼乙醚 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 以56%的产率得到(17S,18S)-tonkinelin
  参考文献：
  名称：

  Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I

  摘要：

  The first synthesis of two possible diastereomers of tonkinelin was achieved. By comparison of the optical rotation of two candidates of tonkinelin and the natural compound, it is suggested that the absolute configuration of natural tonkinelin is likely to be (17S,18S). The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.002
• 作为产物：
  描述：

  碘十六烷 在 bis-triphenylphosphine-palladium(II) chloride AD-mix-α 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 正丁基锂 、 甲基磺酰胺 、 sodium acetate 、 三乙胺 、 N,N-二异丙基乙胺 、 对甲苯磺酰肼 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二醇二乙醚 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 64.67h， 生成 (5S,15'S,16'S)-3-(15'-hydroxy-16'-methoxymethoxyditriacontyl)-5-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I

  摘要：

  The first synthesis of two possible diastereomers of tonkinelin was achieved. By comparison of the optical rotation of two candidates of tonkinelin and the natural compound, it is suggested that the absolute configuration of natural tonkinelin is likely to be (17S,18S). The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.002