(1S,11Z)-[1,10,10-2H3]-hexadec-11-en-1-ol | 495403-59-3

• 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: (1S,11Z)-[1,10,10-2H3]-hexadec-11-en-1-ol
• 英文别名: (Z,1S)-1,10,10-trideuteriohexadec-11-en-1-ol
• CAS: 495403-59-3
• 化学式: C₁₆H₃₂O
• 分子量: 243.406
• InChiKey: RHVMNRHQWXIJIS-VEYHBSCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (1S,11Z)-[1,10,10-2H3]-hexadec-11-en-1-ol 在 Manduca sexta pheromone gland alcohol oxidase 作用下， 以 phosphate buffer 、 正己烷 为溶剂， 反应 48.0h， 以91%的产率得到(11Z)-[1,10,10-2H3]-hexadec-11-enal
  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：

  癸二酸二乙酯 在 P₂-Ni 正丁基锂 、 lithium aluminium deuteride 、 B-isopinocampheyl-9-borabicyclo[3.3.1]nonane 、 Dowex 50 W H⁺ form 、 氨 、 氢溴酸 、 氢气 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 乙二胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 98.5h， 生成 (1S,11Z)-[1,10,10-2H3]-hexadec-11-en-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

文献信息

• Biosynthesis of sex pheromones in moths: stereochemistry of fatty alcohol oxidation in Manduca sexta
  作者：Michal Hoskovec、Anna Luxová、Aleš Svatoš、Wilhelm Boland

  DOI：10.1016/s0040-4020(02)01199-7

  日期：2002.11

  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.