6-(4-dimethylaminophenyl)-4-methylthio-2-oxo-2H-pyran-3-carbonitrile | 667897-80-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(4-dimethylaminophenyl)-4-methylthio-2-oxo-2H-pyran-3-carbonitrile
• 英文别名: 6-[4-(Dimethylamino)phenyl]-4-methylsulfanyl-2-oxopyran-3-carbonitrile
• CAS: 667897-80-5
• 化学式: C₁₅H₁₄N₂O₂S
• 分子量: 286.354
• InChiKey: CLXZCOZMUUHIBH-UHFFFAOYSA-N

物化性质

• 熔点：
  249-251 °C(Solvent: Methanol)
• 沸点：
  420.6±45.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-dimethylaminophenyl)-4-methylthio-2-oxo-2H-pyran-3-carbonitrile 在 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.0h， 生成 4'-(dimethylamino)-3-(piperidin-1-yl)-5-(pyridin-4-yl)-[1,1'-biphenyl]-4-carbonitrile
  参考文献：
  名称：

  A new class of teraryl-based AIEgen for highly selective imaging of intracellular lipid droplets and its detection in advanced-stage human cervical cancer tissues

  摘要：

  设计并合成了一类新的基于 D-π-A teraryl 的 AIEgen 6a，用于细胞内脂滴的选择性染色。

  DOI：

  10.1039/d3tb01764h
• 作为产物：
  描述：

  2-氰-3,3-二(甲硫基)丙烯酸甲酯 、 二甲氨基苯乙酮 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 6-(4-dimethylaminophenyl)-4-methylthio-2-oxo-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  A new class of teraryl-based AIEgen for highly selective imaging of intracellular lipid droplets and its detection in advanced-stage human cervical cancer tissues

  摘要：

  设计并合成了一类新的基于 D-π-A teraryl 的 AIEgen 6a，用于细胞内脂滴的选择性染色。

  DOI：

  10.1039/d3tb01764h

文献信息

• Synthesis and fluorescence of 2<i>h</i>-pyrone derivatives for organic light-emitting diodes (OLED)
  作者：Naoko Mizuyama、Yuka Murakami、Shinya Kohra、Kazuo Ueda、Kyoko Hiraoka、Yoshinori Tominaga、Junko Nagaoka、Kojiro Takahashi、Yasuhiro Shigemitsu

  DOI：10.1002/jhet.5570440120

  日期：2007.1

  2H-Pyrone derivatives were synthesized through the reaction of aryl acetyl compounds with ketene dithioacetals in the presence of sodium hydroxide, and they showed very strong fluorescence in the solid state. The light-emitting region of these 2H-pyrones is 447-630 nm in the solid states.

  2 H-吡喃酮衍生物是通过芳基乙酰基化合物与乙烯酮二硫缩醛在氢氧化钠的存在下反应合成的，它们在固态时显示出非常强的荧光。在固态下，这两个H-吡喃酮的发光区域为447-630 nm。
• Reaction of 6‐aryl‐ or styryl‐4‐methylsulfanyl‐2‐oxo‐2<i>H</i>‐pyrans with active methylene compounds and fluorescence properties of the products
  作者：Naoko Mizuyama、Yuka Murakami、Takatoshi Nakatani、Keiko Kuronita、Shinya Kohra、Kazuo Ueda、Kyoko Hiraoka、Yoshinori Tominaga

  DOI：10.1002/jhet.5570450133

  日期：2008.1

  Abstractmagnified imageNew 2‐pyrone derivatives, dialkyl 3‐cyano‐6‐phenyl‐2‐oxo‐2H‐pyran‐4‐ylmalonates and alkyl 3‐cyano‐6‐phenyl‐2‐oxo‐2H‐pyran‐4‐ylacetates, which were easily prepared by the reaction of 6‐aryl‐4‐methyl‐sulfanyl‐2‐oxo‐2H‐pyran‐3‐carbonitriles with active methylene compounds in the presence of potassium carbonate, show fluorescence emission radiation. The light‐emitting region of dimethyl 3‐cyano‐6‐(4‐N,N‐dimethylamino)styryl‐2‐oxo‐2H‐pyran‐4‐ylmalonate (7h) was 620 nm in dichloromethane, making this compound a typical red fluorescent compound. Methyl 8‐hydroxy‐6‐methyl‐1‐oxo‐3‐phenyl‐1H‐pyrano‐[3,4‐c]pyridine‐5‐carboxylate deriv‐atives also showed fluorescence in the solid state. This is the first example of fluorescence in fused 2‐pyrone derivatives.
• Synthesis and Fluorescence of 6-(4-Dimethylaminophenyl)- and 6-[2-(4-N,N-Disubstituted Aminophenyl)vinyl]-4-methylthio-2-oxo-2H-pyran-3-carbonitriles in Solution and in the Solid States
  作者：Yoshinori Tominaga、Naoko Mizuyama、Yuka Murakami、Junko Nagaoka、Shinya Kohra、Kazuo Ueda、Kyoko Hiraoka、Yasuhiro Shigemitsu

  DOI：10.3987/com-06-10741

  日期：——