11-(tert-butyloxy)-1-undecyne | 139396-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-(tert-butyloxy)-1-undecyne
• 英文别名: 11-[(2-Methylpropan-2-yl)oxy]undec-1-yne
• CAS: 139396-46-6
• 化学式: C₁₅H₂₈O
• 分子量: 224.387
• InChiKey: IGJAQRFOYGFQQY-UHFFFAOYSA-N

物化性质

• 沸点：
  275.7±13.0 °C(Predicted)
• 密度：
  0.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-(tert-butyloxy)-1-undecyne 在 二异丁基氢化铝 、 碘 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 5.0h， 生成 (E)-11-tert-butoxy-1-iodoundec-1-ene
  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：

  10-十一炔醇 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 18.0h， 生成 11-(tert-butyloxy)-1-undecyne
  参考文献：
  名称：

  Novel Antiviral Activity of l-Dideoxy Bicyclic Nucleoside Analogues versus Vaccinia and Measles Viruses in Vitro

  摘要：

  Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with D-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved using novel L-analogues. A structure-activity relationship was established: Antiviral activity versus VACV was highest with an ether side chain with an optimum of n-C9H18-O-n-C5H11. This gave an IC50 of 190 nM, a 60-fold enhancement over the FDA-approved antiviral cidofovir. Interestingly, L-ddBCNAs also inhibit wild type measles virus syncytia formation with a TCID50 of 7.5 mu M for the lead compound. We propose that L-ddBCNAs represent significant innovative antiviral candidates versus measles and poxviruses, and we suggest a mechanism of action versus one or more cellular targets that are essential for viral replication.

  DOI：

  10.1021/jm301778x

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.
• Novel Antiviral Activity of <scp>l</scp>-Dideoxy Bicyclic Nucleoside Analogues versus Vaccinia and Measles Viruses in Vitro
  作者：Christopher McGuigan、Karen Hinsinger、Laura Farleigh、Ranjith N. Pathirana、Joachim J. Bugert

  DOI：10.1021/jm301778x

  日期：2013.2.14

  Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with D-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved using novel L-analogues. A structure-activity relationship was established: Antiviral activity versus VACV was highest with an ether side chain with an optimum of n-C9H18-O-n-C5H11. This gave an IC50 of 190 nM, a 60-fold enhancement over the FDA-approved antiviral cidofovir. Interestingly, L-ddBCNAs also inhibit wild type measles virus syncytia formation with a TCID50 of 7.5 mu M for the lead compound. We propose that L-ddBCNAs represent significant innovative antiviral candidates versus measles and poxviruses, and we suggest a mechanism of action versus one or more cellular targets that are essential for viral replication.