5,6-Heptadien-3-yn-1-ol | 91027-16-6

• 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: 5,6-Heptadien-3-yn-1-ol
• CAS: 91027-16-6
• 化学式: C₇H₈O
• 分子量: 108.14
• InChiKey: RJXTYWWIAGISIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  5,6-Heptadien-3-yn-1-ol 在 一水合肼 作用下， 反应 0.5h， 以71%的产率得到5-Methyl-3-pyrazol-propanol
  参考文献：
  名称：

  在烯基乙炔上区域选择性地加成肼—简便的方法制得3（5）-甲基-5（3）-取代的吡唑

  摘要：

  DOI：

  10.1007/bf00506291
• 作为产物：
  描述：

  7-(trimethylsilyl)hepta-3,6-diyn-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到5,6-Heptadien-3-yn-1-ol
  参考文献：
  名称：

  Total Synthesis of Photoactivatable or Fluorescent Anandamide Probes: Novel Bioactive Compounds with Angiogenic Activity

  摘要：

  Endocannabinoids are endogenous polyunsaturated fatty acids involved in a multitude of health and disease processes. Recently, several lines of evidence suggest the presence of a novel non-CB1/CB2 anandamide receptor in endothelial cells. Thus, we synthesized two types of photoaffinity probes that contain either an arylazide group or a diazirin moiety, together with a fluorescent analogue. The key steps rely on selective hydrogenation of skipped tetrayne backbones and on copper-mediated cross-coupling reactions between diynic precursors. Three synthetic routes were investigated. In biological functional assays, we found that both the arylazide and the fluorescent probes induced robust increases in matrix metalloprotease activity and produced positive angiogenic responses in in vitro endothelial cell tube formation assays. Irradiation of the arylazide probe nicely enhanced this effect in both HUVEC and CBI-KO HUVEC. These results suggest that the arylazide and the fluorescent probes can be used to identify "non-C131/CB2 anandamide receptor" from endothelial cells.

  DOI：

  10.1021/jm8011382

文献信息

• XRIMYAN, A. P.;KARAPETYAN, A. V.;BADANYAN, SH. O., XIMIYA GETEROTSIKL. SOEDIN., 1984, N 2, 230-238
  作者：XRIMYAN, A. P.、KARAPETYAN, A. V.、BADANYAN, SH. O.

  DOI：——

  日期：——
• Regioselective addition of hydrazines to allenylacetylenes ? Convenient route to 3(5)-methyl-5(3)-substituted pyrazoles
  作者：A. P. Khrimyan、A. V. Karapetyan、Sh. O. Badanyan

  DOI：10.1007/bf00506291

  日期：1984.2
• Total Synthesis of Photoactivatable or Fluorescent Anandamide Probes: Novel Bioactive Compounds with Angiogenic Activity
  作者：Laurence Balas、Thierry Durand、Sattyabrata Saha、Inneke Johnson、Somnath Mukhopadhyay

  DOI：10.1021/jm8011382

  日期：2009.2.26

  Endocannabinoids are endogenous polyunsaturated fatty acids involved in a multitude of health and disease processes. Recently, several lines of evidence suggest the presence of a novel non-CB1/CB2 anandamide receptor in endothelial cells. Thus, we synthesized two types of photoaffinity probes that contain either an arylazide group or a diazirin moiety, together with a fluorescent analogue. The key steps rely on selective hydrogenation of skipped tetrayne backbones and on copper-mediated cross-coupling reactions between diynic precursors. Three synthetic routes were investigated. In biological functional assays, we found that both the arylazide and the fluorescent probes induced robust increases in matrix metalloprotease activity and produced positive angiogenic responses in in vitro endothelial cell tube formation assays. Irradiation of the arylazide probe nicely enhanced this effect in both HUVEC and CBI-KO HUVEC. These results suggest that the arylazide and the fluorescent probes can be used to identify "non-C131/CB2 anandamide receptor" from endothelial cells.