11-Oxiranyl-undecanoic acid methyl ester | 152175-57-0

• 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: 11-Oxiranyl-undecanoic acid methyl ester
• 英文别名: Methyl 11-(oxiran-2-yl)undecanoate
• CAS: 152175-57-0
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: QJQOQOLDVZAYNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-Oxiranyl-undecanoic acid methyl ester 在 氢氧化钾 、 copper(l) iodide 、 lithium iodide 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 [14,14,14-2H3]-12-hydroxytetradecanoic acid
  参考文献：
  名称：

  Synthesis of [14,14,14-2H3] 12-hydroxytetradecanoic acid and [13,14-2H2] 11-hydroxytetradecanoic acid useful as tracers to study a (11E)-desaturation reaction in Spodoptera littoralis

  摘要：

  The synthesis of deuterium labeled 11- and 12-hydroxytetradecanoic acids to study a (11E) desaturase in the moth Spodoptera littoralis is reported. [14,14,14-H-2(3)] 12-hydroxytetradecanoic acid was synthesized in four steps from 11-iodo-1-undecene in 49% overall yield. Deuterium was introduced by reaction of an epoxy ester with (CD3)(2)CuLi. The preparation of [13,14-H-2(2)] 11-hydroxytetradecanoic acid was carried out in six steps from 11-bromoundecanoic acid in 55% overall yield. In this case, label was introduced by deuteration of an homoallyl alcohol with D-2, using the Wilkinson catalyst. Incubation of pheromone glands with either of both acids did not lead to the formation of the labeled (11E)-tetradecenoic acid. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00023-5
• 作为产物：
  描述：

  十三烯酸甲酯 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以92%的产率得到11-Oxiranyl-undecanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of [14,14,14-2H3] 12-hydroxytetradecanoic acid and [13,14-2H2] 11-hydroxytetradecanoic acid useful as tracers to study a (11E)-desaturation reaction in Spodoptera littoralis

  摘要：

  The synthesis of deuterium labeled 11- and 12-hydroxytetradecanoic acids to study a (11E) desaturase in the moth Spodoptera littoralis is reported. [14,14,14-H-2(3)] 12-hydroxytetradecanoic acid was synthesized in four steps from 11-iodo-1-undecene in 49% overall yield. Deuterium was introduced by reaction of an epoxy ester with (CD3)(2)CuLi. The preparation of [13,14-H-2(2)] 11-hydroxytetradecanoic acid was carried out in six steps from 11-bromoundecanoic acid in 55% overall yield. In this case, label was introduced by deuteration of an homoallyl alcohol with D-2, using the Wilkinson catalyst. Incubation of pheromone glands with either of both acids did not lead to the formation of the labeled (11E)-tetradecenoic acid. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00023-5