4-(naphthalen-1-ylethynyl)benzaldehyde | 1580484-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(naphthalen-1-ylethynyl)benzaldehyde
• 英文别名: 4-(2-Naphthalen-1-ylethynyl)benzaldehyde；4-(2-naphthalen-1-ylethynyl)benzaldehyde
• CAS: 1580484-68-9
• 化学式: C₁₉H₁₂O
• 分子量: 256.304
• InChiKey: MTTRPSUTFVJZIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(naphthalen-1-ylethynyl)benzaldehyde 、 丙酮 在 L-脯氨酸 作用下， 反应 96.0h， 以51%的产率得到4-hydroxy-4-(4-(naphthalen-1-ylethynyl)phenyl)butan-2-one
  参考文献：
  名称：

  Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO

  摘要：

  Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.007
• 作为产物：
  描述：

  4-三甲基硅乙炔基苯甲醛 在 甲醇 、 四(三苯基膦)钯 、 potassium carbonate 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 44.0h， 生成 4-(naphthalen-1-ylethynyl)benzaldehyde
  参考文献：
  名称：

  Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO

  摘要：

  Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.007

文献信息

• Synthesis of diarylenynes by olefination of 1-arylpropyne with arylaldehyde and their optical properties
  作者：Kenta Shinohara、Takanori Nishida、Ryosuke Wada、Lifen Peng、Yuju Minoda、Akihiro Orita、Junzo Otera

  DOI：10.1016/j.tet.2016.06.018

  日期：2016.7

  A new synthetic protocol of 1-arylpropyne was developed by taking advantage of 1-(diphenylphosphoryl)propyne as propyne equivalent in Sonogashira coupling: consecutive subjection of phosphorylpropyne to t-BuOK and to aryl halides in the presence of Pd and Cu catalysts afforded the corresponding 1-arylpropynes. The following olefination of the 1-arylpropyne with aldehyde provided the corresponding diarylenyne. When the enynes thus obtained were irradiated with UV light, they showed strong emission in organic solvents and in the solid states. In solution, Ph2N-substituted enynes exhibited remarkable solvatofluorochromism, and Lippert-Mataga plot analysis demonstrated that they undergo the larger polarization in the excited states than in the ground states. (C) 2016 Elsevier Ltd. All rights reserved.
• Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO
  作者：Nobuyuki Mase、Taishi Ando、Fumiya Shibagaki、Atsushi Sugita、Tetsuo Narumi、Mitsuo Toda、Naoharu Watanabe、Fujie Tanaka

  DOI：10.1016/j.tetlet.2014.02.007

  日期：2014.3

  Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions. (c) 2014 Elsevier Ltd. All rights reserved.