1-[p-(dimethylamino)phenyl]-4-(p-nitrophenyl)-1,3-butadiyne | 112902-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[p-(dimethylamino)phenyl]-4-(p-nitrophenyl)-1,3-butadiyne
• 英文别名: 1-(4-dimethylaminophenyl)-4-(4-nitrophenyl)-1,3-butadiyne；N,N-Dimethyl-4-[4-(4-nitrophenyl)buta-1,3-diyn-1-yl]aniline；N,N-dimethyl-4-[4-(4-nitrophenyl)buta-1,3-diynyl]aniline
• CAS: 112902-74-6
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: WXZZTYFUMJQUEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  467.8±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[p-(dimethylamino)phenyl]-4-(p-nitrophenyl)-1,3-butadiyne 、 di(9-anthryl) disulfide 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 17.5h， 以63%的产率得到2-[p-(dimethylamino)phenyl]-4-(p-nitrophenyl)-5H-5,9b[1′,2′]-benzenonaphtho[1,2-b]thiophene
  参考文献：
  名称：

  Red and Near-Infrared Photoluminescence of D-π-A-Type Compounds Based on a 1,4-Diaryl-1-thio-1,3-butadiene Conjugated System in a Dibenzobarrelene Skeleton

  摘要：

  1,4-Diaryl-1-thio-1,3-butadiene derivatives having a pi-donor dimethylamino group and several pi-acceptor substituents at both terminals of the conjugated system were synthesized by intramolecular [4 + 2] cycloaddition of 1-thio-enynes and subsequent chemical transformations. They displayed largely red-shifted absorption and emission spectra in solution, the powder state, and in polymer films. The derivatives with a 2,2-dicyanoethenyl group as the p-acceptor exhibited inverted solvatochromism in both optical absorption and fluorescence spectroscopies.

  DOI：

  10.1021/acs.joc.5b02189
• 作为产物：
  描述：

  5-[(3-羧基-5-甲基-4-羰基-2,5-环己二烯-1-亚基)[4-(二乙胺基)苯基]甲基]-3-甲基水杨基<邻羟苄基>酸 、 4-二甲基氨基苯乙炔 在 盐酸羟胺 、 copper dichloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以56%的产率得到1-[p-(dimethylamino)phenyl]-4-(p-nitrophenyl)-1,3-butadiyne
  参考文献：
  名称：

  Red and Near-Infrared Photoluminescence of D-π-A-Type Compounds Based on a 1,4-Diaryl-1-thio-1,3-butadiene Conjugated System in a Dibenzobarrelene Skeleton

  摘要：

  1,4-Diaryl-1-thio-1,3-butadiene derivatives having a pi-donor dimethylamino group and several pi-acceptor substituents at both terminals of the conjugated system were synthesized by intramolecular [4 + 2] cycloaddition of 1-thio-enynes and subsequent chemical transformations. They displayed largely red-shifted absorption and emission spectra in solution, the powder state, and in polymer films. The derivatives with a 2,2-dicyanoethenyl group as the p-acceptor exhibited inverted solvatochromism in both optical absorption and fluorescence spectroscopies.

  DOI：

  10.1021/acs.joc.5b02189

文献信息

• Novel diacetylenic and polydiacetylenic compositions
  申请人：Hoechst Celanese Corporation

  公开号：US04720567A1

  公开（公告）日：1988-01-19

  This invention provides a novel class of diacetylenic monomers and corresponding polydiacetylenic polymers. Illustrative of the invention is a polymer characterized by the repeating unit: ##STR1## In the form of an optically transparent medium with a noncentrosymmetric alignment of molecules, the polymer exhibits exceptional second order nonlinear optical susceptibility effects.

  这项发明提供了一类新型的二乙炔基单体和相应的聚二乙炔基聚合物。该发明的示例是一种以重复单元为特征的聚合物：##STR1## 作为一种具有非中心对称分子排列的光学透明介质，该聚合物表现出异常的二阶非线性光学敏感度效应。
• US4703096A
  申请人：——

  公开号：US4703096A

  公开（公告）日：1987-10-27
• US4711532A
  申请人：——

  公开号：US4711532A

  公开（公告）日：1987-12-08
• US4720567A
  申请人：——

  公开号：US4720567A

  公开（公告）日：1988-01-19
• Red and Near-Infrared Photoluminescence of D-π-A-Type Compounds Based on a 1,4-Diaryl-1-thio-1,3-butadiene Conjugated System in a Dibenzobarrelene Skeleton
  作者：Akihiko Ishii、Yukihiro Makishima、Norio Nakata

  DOI：10.1021/acs.joc.5b02189

  日期：2015.11.20

  1,4-Diaryl-1-thio-1,3-butadiene derivatives having a pi-donor dimethylamino group and several pi-acceptor substituents at both terminals of the conjugated system were synthesized by intramolecular [4 + 2] cycloaddition of 1-thio-enynes and subsequent chemical transformations. They displayed largely red-shifted absorption and emission spectra in solution, the powder state, and in polymer films. The derivatives with a 2,2-dicyanoethenyl group as the p-acceptor exhibited inverted solvatochromism in both optical absorption and fluorescence spectroscopies.