(10E,12Z)-1-(tetrahydro-2H-pyran-2-yloxy)hexadeca-10,12-dien-6-one | 1116649-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (10E,12Z)-1-(tetrahydro-2H-pyran-2-yloxy)hexadeca-10,12-dien-6-one
• CAS: 1116649-59-2
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: JYNYZFUEGDILGF-SCFJQAPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  24.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (10E,12Z)-1-(tetrahydro-2H-pyran-2-yloxy)hexadeca-10,12-dien-6-one 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 62.0h， 以17%的产率得到1,6,6-trifluoro-(10E,12Z)-hexadeca-10,12-diene
  参考文献：
  名称：

  Design and synthesis of bombykol analogues for probing pheromone-binding protein–ligand interactions

  摘要：

  Mono-, difluorinated, and thioanalogues of Bombyx mori female sex pheromones (bombykol, 1) were designed according to the ab initio calculations. These rationally designated analogues were synthesized using hydroboration and Sonogashira coupling strategy via (5E,7Z)-undecadien-1-ol (10) as a common intermediate. A new simplified binding assay based on nanoLC-linear ion trap ESI-MS for quantifying complexation of the B. mori pheromone-binding protein (BmPBP) with native (1) and prepared analogues was developed. The binding properties of native 1 and thioanalogue 4 with PBP were studied in detail. The dissociation constant (K-D) of 1 and 4 was determined to be 2.1 x 10(-6) M and 2.4 x 10(-6) M, respectively. The similar values for both ligands correlated with ab initio calculations. The new binding assay could be used to determine the K-D of other PBPs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.106
• 作为产物：
  描述：

  (10E,12Z)-1-(tetrahydro-2H-pyran-2-yloxy)hexadeca-10,12-dien-6-ol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以90%的产率得到(10E,12Z)-1-(tetrahydro-2H-pyran-2-yloxy)hexadeca-10,12-dien-6-one
  参考文献：
  名称：

  Design and synthesis of bombykol analogues for probing pheromone-binding protein–ligand interactions

  摘要：

  Mono-, difluorinated, and thioanalogues of Bombyx mori female sex pheromones (bombykol, 1) were designed according to the ab initio calculations. These rationally designated analogues were synthesized using hydroboration and Sonogashira coupling strategy via (5E,7Z)-undecadien-1-ol (10) as a common intermediate. A new simplified binding assay based on nanoLC-linear ion trap ESI-MS for quantifying complexation of the B. mori pheromone-binding protein (BmPBP) with native (1) and prepared analogues was developed. The binding properties of native 1 and thioanalogue 4 with PBP were studied in detail. The dissociation constant (K-D) of 1 and 4 was determined to be 2.1 x 10(-6) M and 2.4 x 10(-6) M, respectively. The similar values for both ligands correlated with ab initio calculations. The new binding assay could be used to determine the K-D of other PBPs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.106

文献信息

• Design and synthesis of bombykol analogues for probing pheromone-binding protein–ligand interactions
  作者：Madina Mansurova、Vojtěch Klusák、Petra Nešněrová、Alexander Muck、Jan Doubský、Aleš Svatoš

  DOI：10.1016/j.tet.2008.10.106

  日期：2009.1

  Mono-, difluorinated, and thioanalogues of Bombyx mori female sex pheromones (bombykol, 1) were designed according to the ab initio calculations. These rationally designated analogues were synthesized using hydroboration and Sonogashira coupling strategy via (5E,7Z)-undecadien-1-ol (10) as a common intermediate. A new simplified binding assay based on nanoLC-linear ion trap ESI-MS for quantifying complexation of the B. mori pheromone-binding protein (BmPBP) with native (1) and prepared analogues was developed. The binding properties of native 1 and thioanalogue 4 with PBP were studied in detail. The dissociation constant (K-D) of 1 and 4 was determined to be 2.1 x 10(-6) M and 2.4 x 10(-6) M, respectively. The similar values for both ligands correlated with ab initio calculations. The new binding assay could be used to determine the K-D of other PBPs. (C) 2008 Elsevier Ltd. All rights reserved.