[1,1,10,10-2H4]-dodec-11-yn-1-ol | 495403-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1,1,10,10-2H4]-dodec-11-yn-1-ol
• 英文别名: 1,1,10,10-tetradeuteriododec-11-yn-1-ol
• CAS: 495403-18-4
• 化学式: C₁₂H₂₂O
• 分子量: 186.274
• InChiKey: XNRAUTMOUDUPET-ORZXUFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  13.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [1,1,10,10-2H4]-dodec-11-yn-1-ol 在 Bromotris(Triphenylphosphine)Rhodium(I) 正丁基锂 、 Dowex 50 W H⁺ form 、 氢气 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 10.5h， 生成 [1,10,10-2H3]-hexadecanal
  参考文献：
  名称：

  Biosynthesis of sex pheromones in moths: stereochemistry of fatty alcohol oxidation in Manduca sexta

  摘要：

  Six chiral deuterium labelled metabolic probes, (R) and (S)-enantiomers of [1, 10, 10-H-2(3)]-hexadecan-1-ol, (11E)-[1,10,10-H-2(3)]-hexadec-11-en-1-ol and (11Z)-[1, 10, 10-H-2(3)]-hexadec-11-en-1-ol, were synthesized to examine the stereospecificity of the fatty alcohol oxidase from the female pheromone gland of the tobacco hawk moth (Manduca sexta, Sphingidae). Both in vitro and in vivo oxidations were found to proceed by selective removal of the C1-H-R hydrogen or deuterium atom (Re-specificity) to yield the corresponding aldehydes. (R) and (S)-enantiomers of deuterium labelled salicyl alcohol and 2-thienyl-methanol, compounds entirely chemically diverse from the natural pheromone precursors, were also oxidised Re-specifically to salicylaldehyde and 2-thiophenecarb-aldehyde, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01199-7
• 作为产物：
  描述：

  在 Dowex 50 W H⁺ form 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以12.20 g的产率得到[1,1,10,10-2H4]-dodec-11-yn-1-ol
  参考文献：
  名称：

  Biosynthesis of sex pheromones in moths: stereochemistry of fatty alcohol oxidation in Manduca sexta

  摘要：

  Six chiral deuterium labelled metabolic probes, (R) and (S)-enantiomers of [1, 10, 10-H-2(3)]-hexadecan-1-ol, (11E)-[1,10,10-H-2(3)]-hexadec-11-en-1-ol and (11Z)-[1, 10, 10-H-2(3)]-hexadec-11-en-1-ol, were synthesized to examine the stereospecificity of the fatty alcohol oxidase from the female pheromone gland of the tobacco hawk moth (Manduca sexta, Sphingidae). Both in vitro and in vivo oxidations were found to proceed by selective removal of the C1-H-R hydrogen or deuterium atom (Re-specificity) to yield the corresponding aldehydes. (R) and (S)-enantiomers of deuterium labelled salicyl alcohol and 2-thienyl-methanol, compounds entirely chemically diverse from the natural pheromone precursors, were also oxidised Re-specifically to salicylaldehyde and 2-thiophenecarb-aldehyde, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01199-7