(E)-2-nonadecen-1-ol | 465532-68-7

• 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: (E)-2-nonadecen-1-ol
• 英文别名: (E)-nonadec-2-en-1-ol
• CAS: 465532-68-7
• 化学式: C₁₉H₃₈O
• 分子量: 282.51
• InChiKey: JVJTVCYQAVOSLU-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-nonadecen-1-ol 在 AD-mix-α 、 N-溴代丁二酰亚胺(NBS) 、 甲基磺酰胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 28.17h， 生成 (2S,3S)-1,2-epoxy-3-methoxymethoxynonadecane
  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：

  2-nonadecyn-1-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到(E)-2-nonadecen-1-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

文献信息

• Amphimic acids and related long-chain fatty acids as DNA topoisomerase I inhibitors from an Australian sponge, Amphimedon sp.: Isolation, structure, synthesis, and biological evaluation
  作者：Takayuki Nemoto、Go Yoshino、Makoto Ojika、Youji Sakagami

  DOI：10.1016/s0040-4020(97)10099-0

  日期：1997.12

  fatty acids have been isolated from an Australian sponge, Amphimedon sp., as human DNA topoisomerase I inhibitors. Three of them, amphimic acids A (1)-C (3), are unusual fatty acids possessing a cyclopropylidene group, and one is a new C30 fatty acid 4. Their structures were elucidated by spectroscopic analysis and chemical degradation. The enantioselective synthesis of 1 was carried out to determine

  从澳大利亚海绵Amphimedon sp。中分离出了几种C 27 – C 30不饱和脂肪酸，作为人类DNA拓扑异构酶I抑制剂。其中三个，两性酸A（1）-C（3），是具有环亚丙基的不常见脂肪酸，一个是新的C 30脂肪酸4。通过光谱分析和化学降解阐明了它们的结构。进行1的对映选择性合成以确定两性酸的绝对构型。对这些天然产物和合成衍生物评估了DNA拓扑异构酶I的抑制活性。
• Amphimic acids, novel unsaturated C28 fatty acids as DNA topoisomerase I inhibitors from an Australian sponge Amphimedon sp.
  作者：Takayuki Nemoto、Makoto Ojika、Youji Sakagami

  DOI：10.1016/s0040-4039(97)01234-3

  日期：1997.8

  Amphimic acids A (1) and B (2), novel unsaturated long-chain fatty acids possessing a cyclopropylidene group and inhibiting DNA topoisomerase I, have been isolated from an Australian sponge Amphimedon sp. Their structures were elucidated by spectroscopic analysis and chemical degradation. The enantioselective synthesis of 1 was carried out to determine the absolute configuration. (C) 1997 Elsevier Science Ltd.
• 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.