Tonkinelin | 945026-79-9

• 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: Tonkinelin
• 英文别名: (2S)-4-[(15R,16R)-15,16-dihydroxydotriacontyl]-2-methyl-2H-furan-5-one
• CAS: 945026-79-9
• 化学式: C₃₇H₇₀O₄
• 分子量: 578.96
• InChiKey: MECGDTAEMVIQNQ-DFOKCWARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  41
• 可旋转键数：
  31
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-nonadecyn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 甲基磺酰胺 、 三氟化硼乙醚 、 sodium acetate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 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 59.17h， 生成 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

文献信息

• Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I
  作者：Yasunao Hattori、Hiroyuki Konno、Masato Abe、Hideto Miyoshi、Tetsuhisa Goto、Hidefumi Makabe

  DOI：10.1016/j.bmc.2007.02.002

  日期：2007.4

  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.