diethyl 2-amino-5-(2-thienylmethylideneamino)-3,4-thiophene dicarboxylate | 698978-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: diethyl 2-amino-5-(2-thienylmethylideneamino)-3,4-thiophene dicarboxylate
• 英文别名: 2-Amino-5-[(thiophen-2-ylmethylene)-amino]-thiophene-3,4-dicarboxylic acid diethyl ester；diethyl 2-amino-5-(thiophen-2-ylmethylideneamino)thiophene-3,4-dicarboxylate
• CAS: 698978-91-5
• 化学式: C₁₅H₁₆N₂O₄S₂
• 分子量: 352.435
• InChiKey: DGNAHGQXCGFUSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氰乙酸乙酯 在 sulfur 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 72.67h， 生成 diethyl 2-amino-5-(2-thienylmethylideneamino)-3,4-thiophene dicarboxylate
  参考文献：
  名称：

  一种2,5-二氨基-3,4-噻吩二羧酸乙酯衍生物的 制备方法和用途

  摘要：

  本发明涉及一种2,5-二氨基-3,4-噻吩二羧酸乙酯衍生物的制备方法和用途，该类化合物以硫黄和氰基乙酸乙酯为原料，在三乙胺的催化下，与取代苯甲醛或芳杂环醛缩合得到。采用MTT法对所合成的化合物进行了人乳腺癌细胞(T47D、MCF-7)、人宫颈癌细胞(Hela)、人子宫内膜癌细胞(Ishikawa)的抗肿瘤活性筛选，实验结果表明：化合物1，2b，2c，2e，2h-2l对T47D细胞株的抑制活性明显；化合物2a，2b，2c，2h，2j对MCF-7的抑制作用较强；化合物2j对四种癌细胞株均表现出了很强的抑制活性，对于MCF-7、Hela和Ishikawa三种癌细胞株的IC50分别为2.4μM、4.7μM和7.6μM，均好与阳性对照药阿霉素。本发明所采用的制备方法反应条件温和，实验步骤简捷。

  公开号：

  CN104016963B

文献信息

• Tuning of the photophysical and electrochemical properties of symmetric and asymmetric conjugated thiophenoazomethines
  作者：Shengzhen Liu、Ti Wu、Qi Zhu、Jialing Pu、Guangxue Chen、Weimin Zhang、Zhongxiao Li

  DOI：10.1039/c8ra00570b

  日期：——

  have a great effect on the electronic absorption and energy levels of the conjugated compounds, particularly the effect of terminal groups. The terminal withdrawing and donating groups of thiophenoazomethines led to the formation of an electronic push–pull, push–push and pull–pull system, which can perturb the electronic transitions between the ground and excited states. The flexible chain substituents

  通过容易获得的胺与各种醛的反应，实现了通往对称和不对称噻吩并亚甲基的合成路线。对该方法得到的一系列噻吩并亚甲基的研究表明，末端基团和共轭程度对共轭化合物的电子吸收和能级有很大影响，尤其是末端基团的影响。噻吩并亚甲基的末端撤离和供体基团导致形成电子推拉、推拉和拉拉系统，这可以扰乱基态和激发态之间的电子跃迁。噻吩单元上的柔性链取代基提高了其溶解度，也导致了红移吸收，但对能级的影响有限。
• Conjugated Thiophenes Having Conducting Properties and Synthesis of Same
  申请人：Skene G. William

  公开号：US20070287842A1

  公开（公告）日：2007-12-13

  The present invention relates to conjugated oligomers and polymers comprising aromatic thiophene cores. The conjugated materials are obtained by simple and efficient condensation of an aryl diamine and an aryl dialdehyde or a bifunctional aryl moiety comprising both an aldehyde and an amine. Condensation of the complementary moieties at temperatures ranging from ambient to refluxing temperatures in various solvents resulted in conjugated oligomers and polymers that can subsequently be cast into thin films. Oligomerization and polymerization can be done under mild conditions with removal of the resulting water bi-product responsible for shifting the equilibrium in favour of the conjugated products. The resulting conjugated compounds can be made conducting with dopants affording electrically conducting materials of either p-type or n-type conductors depending on the dopant selected.

  本发明涉及含有芳香硫吡咯核的共轭寡聚物和聚合物。这些共轭材料是通过芳香族二胺和芳香族二醛或具有同时含有醛和胺的双官能团芳香族基团的简单而有效的缩合反应获得的。在各种溶剂中，在从常温到沸点温度的温度范围内缩合互补的官能团，得到了可以随后铸造成薄膜的共轭寡聚物和聚合物。在温和的条件下进行寡聚和聚合，去除产生的水副产物，有利于使平衡向共轭产物方向移动。所得的共轭化合物可以通过掺杂制成导电材料，根据所选择的掺杂剂，可以得到p型或n型导体的电导材料。
• CONJUGATED THIOPHENES HAVING CONDUCTING PROPERTIES AND SYNTHESIS OF SAME
  申请人：Skene William G.

  公开号：US20120004386A1

  公开（公告）日：2012-01-05

  The present invention relates to conjugated oligomers and polymers comprising aromatic thiophene cores. The conjugated materials are obtained by simple and efficient condensation of an aryl diamine and an aryl dialdehyde or a bifunctional aryl moiety comprising both an aldehyde and an amine. Condensation of the complementary moieties at temperatures ranging from ambient to refluxing temperatures in various solvents resulted in conjugated oligomers and polymers that can subsequently be cast into thin films. Oligomerization and polymerization can be done under mild conditions with removal of the resulting water bi-product responsible for shifting the equilibrium in favour of the conjugated products. The resulting conjugated compounds can be made conducting with dopants affording electrically conducting materials of either p-type or n-type conductors depending on the dopant selected.

  本发明涉及含有芳香硫杂苯核的共轭寡聚物和聚合物。这些共轭材料是通过芳香族二胺和芳香族二醛或含有醛和胺的双官能团芳香族基团的简单高效缩合反应得到的。在各种溶剂中，将互补的官能团在环境温度到沸腾温度范围内缩合，得到共轭寡聚物和聚合物，随后可以将其铸造成薄膜。在温和的条件下进行寡聚和聚合反应，通过去除生成的水分子，使平衡向共轭产物倾斜。所得的共轭化合物可以通过掺杂剂使其导电，从而获得p型或n型导体的电导材料。
• Conjugated thiophenes having conducting properties and synthesis of same
  申请人：Université de Montréal

  公开号：US08034895B2

  公开（公告）日：2011-10-11

  The present invention relates to conjugated oligomers and polymers comprising aromatic thiophene cores. The conjugated materials are obtained by simple and efficient condensation of an aryl diamine and an aryl dialdehyde or a bifunctional aryl moiety comprising both an aldehyde and an amine. Condensation of the complementary moieties at temperatures ranging from ambient to refluxing temperatures in various solvents resulted in conjugated oligomers and polymers that can subsequently be cast into thin films. Oligomerization and polymerization can be done under mild conditions with removal of the resulting water bi-product responsible for shifting the equilibrium in favor of the conjugated products. The resulting conjugated compounds can be made conducting with dopants affording electrically conducting materials of either p-type or n-type conductors depending on the dopant selected.

  本发明涉及含芳香硫吡咯核的共轭寡聚体和聚合物。这些共轭材料是通过芳香族二胺和芳香族二醛或含有醛和胺的双功能芳香族基团的简单高效缩合反应得到的。在各种溶剂中，在从室温到沸点温度的温度下，互补基团的缩合反应结果形成了共轭寡聚体和聚合物，随后可以将其铸造成薄膜。在温和的条件下进行寡聚和聚合反应，并通过去除产生的水副产物来促进共轭产物的生成。所得到的共轭化合物可以通过掺杂剂进行导电，从而获得p型或n型导体的电导材料。
• 一种2,5-二氨基-3,4-噻吩二羧酸乙酯衍生物的 制备方法和用途
  申请人：中国科学院新疆理化技术研究所

  公开号：CN104016963B

  公开（公告）日：2016-04-06

  本发明涉及一种2,5-二氨基-3,4-噻吩二羧酸乙酯衍生物的制备方法和用途，该类化合物以硫黄和氰基乙酸乙酯为原料，在三乙胺的催化下，与取代苯甲醛或芳杂环醛缩合得到。采用MTT法对所合成的化合物进行了人乳腺癌细胞(T47D、MCF-7)、人宫颈癌细胞(Hela)、人子宫内膜癌细胞(Ishikawa)的抗肿瘤活性筛选，实验结果表明：化合物1，2b，2c，2e，2h-2l对T47D细胞株的抑制活性明显；化合物2a，2b，2c，2h，2j对MCF-7的抑制作用较强；化合物2j对四种癌细胞株均表现出了很强的抑制活性，对于MCF-7、Hela和Ishikawa三种癌细胞株的IC50分别为2.4μM、4.7μM和7.6μM，均好与阳性对照药阿霉素。本发明所采用的制备方法反应条件温和，实验步骤简捷。