2,6-bis((1-methyl-1H-pyrrol-2-yl)methylene)cyclohexan-1-one | 94386-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,6-bis((1-methyl-1H-pyrrol-2-yl)methylene)cyclohexan-1-one
• 英文别名: 2,6-Bis[(1-methylpyrrol-2-yl)methylidene]cyclohexan-1-one
• CAS: 94386-21-7
• 化学式: C₁₈H₂₀N₂O
• mdl: MFCD04001857
• 分子量: 280.37
• InChiKey: VTZLPXIVTAFLQG-UHFFFAOYSA-N

物化性质

• 沸点：
  499.9±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 2,6-bis((1-methyl-1H-pyrrol-2-yl)methylene)cyclohexan-1-one 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (9E)-1,3-dimethyl-5-(1-methylpyrrol-2-yl)-9-[(1-methylpyrrol-2-yl)methylidene]-7,8-dihydro-6H-pyrimido[4,5-b]quinoline-2,4-dione
  参考文献：
  名称：

  The products of the reaction between 6-amine-1,3-dimethyl uracil and bis-chalcones induce cytotoxicity with massive vacuolation in HeLa cervical cancer cell line

  摘要：

  As a part of our research in the chemistry of chalcones we have prepared four pyrimidine monoadducts of bis-chalcones through the reaction with 6-amino-1,3-dimethyl uracil. These compounds displayed cytotoxicity with a massive vacuolation in different human cell lines in vitro. Compound 6 was the most cytotoxic inducer of vacuoles, this compound induced G1 phase cell cycle arrest, and their cytotoxicity went without morphological and biochemical evidence of apoptotic cell death in HeLa cells. In addition, our results showed that this vacuole formation does not require de novo protein synthesis and the content vacuolar is acidic. Compound 6 induce necrotic cell death with excessive vacuolation, similar to a process of autophagy. Spautin-1 an inhibitor of autophagy, decreased the transformation of microtubule-associated protein 1 light chain 3 (LC3B-I) to LC3B-II and the vacuolation induced by compound 6 in HeLa cells, both autophagy processes. These compounds could be of pivotal importance in the study of non-apoptotic cell death with vacuole formation and could be useful in research into new autophagy inhibitors agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.021
• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 、 环己酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以70%的产率得到2,6-bis((1-methyl-1H-pyrrol-2-yl)methylene)cyclohexan-1-one
  参考文献：
  名称：

  405/460 nm LED灯下基于吡咯的烯酮染料作为自由基光引发剂：酮结构的影响

  摘要：

  烯酮染料作为光引发剂在可见光诱导的光致聚合反应中获得了极大的关注。但是，尚未完全揭示烯酮的光化学反应性的结构关系，该结构关系强烈地决定了它们的引发效率。在这项工作中，通过N-甲基吡咯-2-醛与四种不同的酮的缩合反应合成了基于吡咯的烯酮（PYO），得到了C3PY，C6PY，C6NPY和C6SPY。发现酮部分的变化稍微影响了它们的吸收性能，但是显着改变了它们的光物理行为。因此，当与少量盐或三乙醇胺作为添加剂一起使用时，PYO对丙烯酸酯单体的引发性能彼此不同，这与光解实验结果一致。DFT计算证明，在酮部分加成六元环会降低C6PY，C6NPY和C6SPY的分子平面度，从而提高它们的内部转化率并降低其光化学反应性。这项工作为烯酮染料的结构性质关系领域提供了有意义的信息。

  DOI：

  10.1016/j.dyepig.2021.109372

文献信息

• Pyrrole-based enone dyes as radical photointiator under 405/460 nm LED lamp: The effect of ketone structure
  作者：Tanlong Xue、Yang Li、Liqun Tang、Ruifen Tang、Jun Nie、Xiaoqun Zhu

  DOI：10.1016/j.dyepig.2021.109372

  日期：2021.7

  pyrrole-based enones (PYOs) were synthesized by the condensation of N-methypyrrole-2-aldehyde and four different ketones, yielding C3PY, C6PY, C6NPY, and C6SPY. It was found that variation of ketone part slightly affected their absorption properties but significantly changed their photophysical behavior. Accordingly, initiation performance of PYOs toward an acrylate monomer, when co-used with onimum salt or

  烯酮染料作为光引发剂在可见光诱导的光致聚合反应中获得了极大的关注。但是，尚未完全揭示烯酮的光化学反应性的结构关系，该结构关系强烈地决定了它们的引发效率。在这项工作中，通过N-甲基吡咯-2-醛与四种不同的酮的缩合反应合成了基于吡咯的烯酮（PYO），得到了C3PY，C6PY，C6NPY和C6SPY。发现酮部分的变化稍微影响了它们的吸收性能，但是显着改变了它们的光物理行为。因此，当与少量盐或三乙醇胺作为添加剂一起使用时，PYO对丙烯酸酯单体的引发性能彼此不同，这与光解实验结果一致。DFT计算证明，在酮部分加成六元环会降低C6PY，C6NPY和C6SPY的分子平面度，从而提高它们的内部转化率并降低其光化学反应性。这项工作为烯酮染料的结构性质关系领域提供了有意义的信息。
• The products of the reaction between 6-amine-1,3-dimethyl uracil and bis-chalcones induce cytotoxicity with massive vacuolation in HeLa cervical cancer cell line
  作者：José D. Solano、Ignacio González-Sánchez、Marco A. Cerbón、Ángel Guzmán、Miguel A. Martínez-Urbina、Miguel A. Vilchis-Reyes、Eduardo C. Martínez-Zuñiga、Cuauhtémoc Alvarado、Angelina Quintero、Eduardo Díaz

  DOI：10.1016/j.ejmech.2012.12.021

  日期：2013.2

  As a part of our research in the chemistry of chalcones we have prepared four pyrimidine monoadducts of bis-chalcones through the reaction with 6-amino-1,3-dimethyl uracil. These compounds displayed cytotoxicity with a massive vacuolation in different human cell lines in vitro. Compound 6 was the most cytotoxic inducer of vacuoles, this compound induced G1 phase cell cycle arrest, and their cytotoxicity went without morphological and biochemical evidence of apoptotic cell death in HeLa cells. In addition, our results showed that this vacuole formation does not require de novo protein synthesis and the content vacuolar is acidic. Compound 6 induce necrotic cell death with excessive vacuolation, similar to a process of autophagy. Spautin-1 an inhibitor of autophagy, decreased the transformation of microtubule-associated protein 1 light chain 3 (LC3B-I) to LC3B-II and the vacuolation induced by compound 6 in HeLa cells, both autophagy processes. These compounds could be of pivotal importance in the study of non-apoptotic cell death with vacuole formation and could be useful in research into new autophagy inhibitors agents. (C) 2012 Elsevier Masson SAS. All rights reserved.