1,3,5-tris(2-thienyl)-2,4-diazapenta-1,4-diene | 114261-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1,3,5-tris(2-thienyl)-2,4-diazapenta-1,4-diene
• 英文别名: 2-thienyl-N,N-bis(2-thienylmethylene)methanediamine；1-thiophen-2-yl-N-[thiophen-2-yl-(thiophen-2-ylmethylideneamino)methyl]methanimine
• CAS: 114261-50-6
• 化学式: C₁₅H₁₂N₂S₃
• 分子量: 316.472
• InChiKey: JFBOACJJWSHXAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(2-thienyl)-2,4-diazapenta-1,4-diene 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84%的产率得到双-噻吩-2-甲基胺
  参考文献：
  名称：

  Highly chemoselective reductive amination-coupling by one-pot reaction of aldehydes, HMDS and NaBH4

  摘要：

  An efficient and highly chemoselective synthesis of symmetrical secondary amines via reductive amination of aldehydes with inexpensive and commercially available HMDS and sodium borohydride in high to quantitative yields is reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.048
• 作为产物：
  描述：

  2-噻吩甲醛 在 氨 作用下， 以 甲醇 为溶剂， 生成 1,3,5-tris(2-thienyl)-2,4-diazapenta-1,4-diene
  参考文献：
  名称：

  三烯丙基硼烷与氨和脂肪胺作为化学计量的烯丙基化剂进行羰基化合物的氨化反应的加成反应

  摘要：

  三烯丙基硼烷-胺加合物在甲醇中羰基化合物的氨基烯丙基化反应中是有效的化学计量烯丙基化剂。此外，用三烯丙基硼烷-甲胺加合物实现了铜催化的埃尔曼亚胺的非对映选择性烯丙基化。

  DOI：

  10.1021/acs.orglett.8b01317

文献信息

• A novel tricarbonyl rhenium complex of 2-thienyl-N,N-bis(2-thienylmethylene)methanediamine – X-ray structure, spectroscopic characterisation and DFT calculations
  作者：B. Machura、R. Kruszynski、J. Kusz

  DOI：10.1016/j.poly.2006.12.038

  日期：2007.7

  The reaction of Re(CO)(5)Cl with 2-thienyl-N,N-bis(2-thienylmethylene)methanediamine (tbtmma) has been examined and a novel Re(CO)(3)(+) tricarbonyl -fac-[Re(CO)(3)(tbtmma)Cl] - has been obtained. The compound has been studied by IR, U-V-Vis spectroscopy and X-ray crystallography. The molecular orbital diagram of the tricarbonyl has been calculated with the density functional theory (DFT) method. The spin-allowed singlet-singlet electronic transitions of [Re(CO)(3)(tbtmma)Cl] have been calculated with the time-dependent DFT method, and the UV-Vis spectrum of the title compound has been discussed on this basis. (c) 2007 Elsevier Ltd. All rights reserved.
• ——
  作者：N. A. Lozinskaya

  DOI：10.1023/a:1023915024572

  日期：——

  Novel data were obtained concerning the reaction of aromatic aldehydes with ammonia. A preparative method for the synthesis of new substituted 1,3,5-triaryl-2,4-diazapenta-1,4-dienes was developed. These products are the starting reactants for syntheses of cis- and trans-2,4,5-triaryl-2-imidazolines and 2,4,5-triarylimidazoles.
• Antioxidant activity and redox properties of cis-2,4,5-tris(hydroxyaryl)imidazolines
  作者：Daniil R. Bazanov、Victoria Yu. Savitskaya、Natalia A. Maximova、Vladimir Yu. Tyurin、Yulia A. Gracheva、Natalia B. Chesnokova、Olga V. Beznos、Sergey E. Sosonyuk、Natalia A. Lozinskaya

  DOI：10.1016/j.mencom.2022.09.038

  日期：2022.9