16-(methoxymethoxy)hexadeca-3,5-diyne-1,1,1,2,2-d5 | 160206-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 16-(methoxymethoxy)hexadeca-3,5-diyne-1,1,1,2,2-d5
• CAS: 160206-54-2
• 化学式: C₁₈H₃₀O₂
• 分子量: 283.395
• InChiKey: SSDRYEJOWSMVAV-WNWXXORZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  20.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  16-(methoxymethoxy)hexadeca-3,5-diyne-1,1,1,2,2-d5 在 盐酸 、 重铬酸吡啶 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  Synthesis of [16,16,16-2H3] 11-hexadecynoic acid and [15,15,16,16,16-2H5] (Z,Z)-11,13-hexadecadienoic acid and their use as tracers in a key step of the sex pheromone biosynthesis of the processionary moth.

  摘要：

  The synthesis of deuterium labeled 11-hexadecynoic acid and (Z,Z)-11,13-hexadecadienoic acid and their use to investigate the biosynthetic pathway of the processionary moth sex pheromone is reported. In [16,16,16-H-2(3)] 11-hexadecynoic acid, deuterium atoms were introduced by reaction of iodoalkyne 6b with (CD3)(2)CuLi. Alkylation of terminal diyne 14b with CD3CD2I followed by stereoselective reduction of the corresponding diyne to the corresponding (Z,Z) diene afforded [15,15,16,16,16-H-2(5)] (Z,Z)-11,13-hexadecadienoic acid. GLC-MS analyses of extracts from pheromone glands incubated with these tracers revealed that the acetylenic acid, but not the dienoic acid, is a precursor of the pheromone enyne system.

  DOI：

  10.1016/s0040-4020(01)85545-9
• 作为产物：
  描述：

  在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 3.0h， 生成 16-(methoxymethoxy)hexadeca-3,5-diyne-1,1,1,2,2-d5
  参考文献：
  名称：

  Synthesis of [16,16,16-2H3] 11-hexadecynoic acid and [15,15,16,16,16-2H5] (Z,Z)-11,13-hexadecadienoic acid and their use as tracers in a key step of the sex pheromone biosynthesis of the processionary moth.

  摘要：

  The synthesis of deuterium labeled 11-hexadecynoic acid and (Z,Z)-11,13-hexadecadienoic acid and their use to investigate the biosynthetic pathway of the processionary moth sex pheromone is reported. In [16,16,16-H-2(3)] 11-hexadecynoic acid, deuterium atoms were introduced by reaction of iodoalkyne 6b with (CD3)(2)CuLi. Alkylation of terminal diyne 14b with CD3CD2I followed by stereoselective reduction of the corresponding diyne to the corresponding (Z,Z) diene afforded [15,15,16,16,16-H-2(5)] (Z,Z)-11,13-hexadecadienoic acid. GLC-MS analyses of extracts from pheromone glands incubated with these tracers revealed that the acetylenic acid, but not the dienoic acid, is a precursor of the pheromone enyne system.

  DOI：

  10.1016/s0040-4020(01)85545-9