2-(but-3-yn-1-yl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione | 1416169-99-7

• 英文名称: 2-(but-3-yn-1-yl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 1416169-99-7
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: UZYOTNRKRKGACF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-戊炔 、 2-(but-3-yn-1-yl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione 在 copper(l) iodide 、 nickel(II) chloride hexahydrate 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以71%的产率得到C₁₈H₂₀O₄
  参考文献：
  名称：

  Alkyne-Tag Raman Imaging for Visualization of Mobile Small Molecules in Live Cells

  摘要：

  Alkyne has a unique Raman band that does not overlap with Raman scattering from any endogenous molecule in live cells. Here, we show that alkyne-tag Raman imaging (ATRI) is a promising approach for visualizing nonimmobilized small molecules in live cells. An examination of structure Raman shift/intensity relationships revealed that alkynes conjugated to an aromatic ring and/or to a second allcyne (conjugated diynes) have strong Raman signals in the cellular silent region and can be excellent tags. Using these design guidelines, we synthesized and imaged a series of alkyne-tagged coenzyme Q (CoQ) analogues in live cells. Cellular concentrations of diyne-tagged Coganalogues could be semiquantitatively estimated. Finally, simultaneous imaging of two small molecules, 5-ethynyl-2 '-deoxyuridine (EdU) and a Cog analogue, with distinct Raman tags was demonstrated.

  DOI：

  10.1021/ja308529n
• 作为产物：
  描述：

  2,3,4,5-四甲氧基-6-甲基苯甲醛 在 ammonium cerium (IV) nitrate 、 吡啶-2,6-二甲酸 、 2-氮杂金刚烷-N-氧自由基 、 碘苯二乙酸 、 palladium on activated charcoal 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 、 mineral oil 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.91h， 生成 2-(but-3-yn-1-yl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Alkyne-Tag Raman Imaging for Visualization of Mobile Small Molecules in Live Cells

  摘要：

  Alkyne has a unique Raman band that does not overlap with Raman scattering from any endogenous molecule in live cells. Here, we show that alkyne-tag Raman imaging (ATRI) is a promising approach for visualizing nonimmobilized small molecules in live cells. An examination of structure Raman shift/intensity relationships revealed that alkynes conjugated to an aromatic ring and/or to a second allcyne (conjugated diynes) have strong Raman signals in the cellular silent region and can be excellent tags. Using these design guidelines, we synthesized and imaged a series of alkyne-tagged coenzyme Q (CoQ) analogues in live cells. Cellular concentrations of diyne-tagged Coganalogues could be semiquantitatively estimated. Finally, simultaneous imaging of two small molecules, 5-ethynyl-2 '-deoxyuridine (EdU) and a Cog analogue, with distinct Raman tags was demonstrated.

  DOI：

  10.1021/ja308529n