dodeca-5,7-diyndiyn-1-ol | 960129-20-8

• 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: dodeca-5,7-diyndiyn-1-ol
• 英文别名: dodeca-5,7-diyn-1-ol
• CAS: 960129-20-8
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: JPDXRJZFOLLUJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  309.6±25.0 °C(Predicted)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  dodeca-5,7-diyndiyn-1-ol 在 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 反应 0.17h， 以75%的产率得到3-(hex-1-ynyl)-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine
  参考文献：
  名称：

  Discovery, Synthetic Methodology, and Biological Evaluation for Antiphotoaging Activity of Bicyclic[1,2,3]triazoles: In Vitro and in Vivo Studies

  摘要：

  Novel bicyclic[1,2,3]triazoles (4, 7, 11, 15) have been synthesized using a one-pot metal free strategy with high structural diversity as photoprotective agents, and their effect on UVA-induced senescence in human dermal fibroblast cells (FB) and the associated mechanism are delineated. lid plus UVA can induce a decrease in reactive oxygen species (ROS) production and senescence-associated beta-galactosiclase (SA-beta-gal) activity but an increase in adenosine triphosphate (ATP) synthesis and mitochondrial membrane potential (Delta psi(mt)). The mRNA levels of six senescence-associated genes, matrix metalloproteinase-1 (MMP-1), was decreased, while elastin, procollagen I type I, fibronectin, COL1 alpha 1, and tissue inhibitor of metalloproteinase-1 (TIMP-1) were increased. lid plus UVA also decreased MMP-1 and increased TIMP-1 protein levels. Additionally, the thickness of the minim dorsal skin and epidermis, by UVA, was decreased by topical lid treatment. Our results indicate that bicyclic[1,2,3]triazoles protect UVA-induced senescence-like characteristics in FB cells, which may provide potential prevention against photoaging.

  DOI：

  10.1021/jm400394s
• 作为产物：
  描述：

  5-己炔-1-醇 、 1-己炔 在 copper(l) iodide 、 四甲基乙二胺 、 三乙胺 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以75%的产率得到dodeca-5,7-diyndiyn-1-ol
  参考文献：
  名称：

  Discovery, Synthetic Methodology, and Biological Evaluation for Antiphotoaging Activity of Bicyclic[1,2,3]triazoles: In Vitro and in Vivo Studies

  摘要：

  Novel bicyclic[1,2,3]triazoles (4, 7, 11, 15) have been synthesized using a one-pot metal free strategy with high structural diversity as photoprotective agents, and their effect on UVA-induced senescence in human dermal fibroblast cells (FB) and the associated mechanism are delineated. lid plus UVA can induce a decrease in reactive oxygen species (ROS) production and senescence-associated beta-galactosiclase (SA-beta-gal) activity but an increase in adenosine triphosphate (ATP) synthesis and mitochondrial membrane potential (Delta psi(mt)). The mRNA levels of six senescence-associated genes, matrix metalloproteinase-1 (MMP-1), was decreased, while elastin, procollagen I type I, fibronectin, COL1 alpha 1, and tissue inhibitor of metalloproteinase-1 (TIMP-1) were increased. lid plus UVA also decreased MMP-1 and increased TIMP-1 protein levels. Additionally, the thickness of the minim dorsal skin and epidermis, by UVA, was decreased by topical lid treatment. Our results indicate that bicyclic[1,2,3]triazoles protect UVA-induced senescence-like characteristics in FB cells, which may provide potential prevention against photoaging.

  DOI：

  10.1021/jm400394s

文献信息

• Harnessing by a diacetylene unit: a molecular design for porous two-dimensional network formation at the liquid/solid interface
  作者：Kazukuni Tahara、Jinne Adisoejoso、Koji Inukai、Shengbin Lei、Aya Noguchi、Bing Li、Willem Vanderlinden、Steven De Feyter、Yoshito Tobe

  DOI：10.1039/c3cc47949h

  日期：——

  Through the precise molecular design for alkoxy dehydro[12]annulene derivatives harnessed by a diacetylene unit in each alkyl chain, porous two-dimensional networks with giant pores were formed at the liquid/graphite interface.

  通过精确的分子设计，将每个烷基链中的二炔单元用于操控烷氧脱氢[12]环烯衍生物，在液体/石墨界面形成了具有巨孔的二维多孔网络。
• Synthesis and properties of diacetylene azides
  作者：I. N. Domnin、L. A. Remizova

  DOI：10.1134/s1070428009080028

  日期：2009.8

  A three-stage method was developed for the synthesis of diacetylene azides from diacetylene alcohols prepared by Cadiot-Chodkiewicz reaction. By their bromination the corresponding diacetylene bromides were obtained whose azidation resulted in the target diacetylene azides. The attempt was performed to prepare azides of triacetylene series, but the low stability of the synthesized triacetylene alcohols prevented their conversion into the corresponding bromides.