(3S,4S)-5-methoxymethoxy-1-docosyn-4-ol | 937182-40-6

• 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: (3S,4S)-5-methoxymethoxy-1-docosyn-4-ol
• CAS: 937182-40-6
• 化学式: C₂₃H₄₄O₃
• 分子量: 368.601
• InChiKey: IKOWUBQWHBBNBN-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  26.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-5-methoxymethoxy-1-docosyn-4-ol 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium acetate 、 三乙胺 、 对甲苯磺酰肼 作用下， 以 乙二醇二乙醚 、 水 为溶剂， 反应 16.0h， 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
• 作为产物：
  描述：

  碘十六烷 在 AD-mix-α 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 正丁基锂 、 甲基磺酰胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 48.67h， 生成 (3S,4S)-5-methoxymethoxy-1-docosyn-4-ol
  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