1,2-bis-(4-dimethylaminophenyl)-2-hydroxyethanone | 57806-83-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis-(4-dimethylaminophenyl)-2-hydroxyethanone
• 英文别名: 4,4'-Bis-dimethylamino-benzoin；1,2-Bis[4-(dimethylamino)phenyl]-2-hydroxyethanone
• CAS: 57806-83-4
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: NNIIDCLUJCRWNC-UHFFFAOYSA-N

物化性质

• 熔点：
  153-156 °C
• 沸点：
  491.6±45.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis-(4-dimethylaminophenyl)-2-hydroxyethanone 以 乙醇 为溶剂， 生成 4,4’-双(二甲基)苯酯
  参考文献：
  名称：

  Cytotoxicity of New Selenoimine, Selenonitrone and Nitrone Derivatives Against Human Breast Cancer MDA-MB231 Cells

  摘要：

  A series of new nitrone, selenoimine and selenonitrone derivatives were synthesized. Nitrone and selenonitrone derivatives were synthesized through the condensation reaction between N-mono substitutedhydroxylamine and carbonyl compounds substituted with electron donating groups, such as di(4-methoxy)benzoyl diselenide, 4-(N, N-dimethylamino) benzoyl selenonitrile and 4, 4'-di(N, N- dimethylamino)benzil, afforded a variety of new nitrone and selenonitrone compounds. Selenoimine derivative was synthesized through the condensation reaction between tert-butyl amine and (4-methoxybenzoyl selenonitrile). The yield of synthesized compounds (N-1, N-2, N-3, N-4 and N-5 were (66, 60, 61, 62 and 45) %, respectively. The structures of the synthesized compounds were characterized by FT-IR, H-1-NMR, C-13-NMR, and mass spectra. Cytotoxicity of selenonitrone (N-1) and selenoimine (N-3) derivatives against breast cancer cells (MDA-MB231) were evaluated for 24 and 48 h via MTT assay. The IC50 value of compound N-1 was 1.714 and 1.897 mu M for 24 h and 48 h, respectively. The IC50 value of compound N-3 was 1.438 and 2.469 mu M for 24 h and 48 h, respectively. The results suggested selenonitrone (N-1) and selenoimine (N-3) as anti-breast cancer potential lead compound with future merit investigations.

  DOI：

  10.21608/ejchem.2020.31747.2675
• 作为产物：
  描述：

  对二甲氨基苯甲醛 在 三氢化钐 、 potassium iodide 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以67%的产率得到1,2-bis-(4-dimethylaminophenyl)-2-hydroxyethanone
  参考文献：
  名称：

  铜（I）/钐将醛意外转化为安息香类

  摘要：

  摘要 使用涉及钐的各种还原剂将醛还原偶联生成频哪醇是众所周知的。然而，在本报告中，用 Cu(I)/Sm 系统处理芳香醛以良好的收率产生了苯甲酸和/或苯甲醚。提出了一种可能的机制，其中 Cu(I) 不仅激活 Sm 金属，而且促进中间体的脱氢，在此过程中可能涉及 Cu(III) 物种。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要

  DOI：

  10.1080/00397911.2013.804572

文献信息

• Amine-Linked N-Heterocyclic Carbenes: The Importance of an Pendant Free-Amine Auxiliary in Assisting the Catalytic Reaction
  作者：Chia-Yi Li、Yi-Yin Kuo、Jie-Hong Tsai、Glenn P. A. Yap、Tiow-Gan Ong

  DOI：10.1002/asia.201000829

  日期：2011.6.6

  amine group, leading to insight about the instability of NHCs arising from the intermolecular interaction of the dangling amine side‐arm. However, the pendant amine plays an important role with respect to the catalytic process, resuscitating the catalytic activity of unsaturated NHC’s through a synergistic effect invoked by the secondary amine. This proof of concept allows us to expand the spectrum of

  我们已经成功地扩展了胺基上具有不同取代基的氨基-NHC库，从而使人们对悬空的胺侧臂之间的分子间相互作用引起的NHC不稳定性有了更深入的了解。然而，侧链胺在催化过程中起着重要作用，通过仲胺引起的协同作用来恢复不饱和NHC的催化活性。这一概念证明使我们能够将催化范围扩展到C CC以及CB键的形成。
• Unexpected Transformation of Aldehydes into Benzoins with Copper(I)/Samarium
  作者：Yongjun Liu、Hui Wang、Yulong Fu、Yan Qi、Kuiwei Yang

  DOI：10.1080/00397911.2013.804572

  日期：2014.1.17

  Abstract The reductive coupling of aldehydes to afford pinacolic alcohols using all kinds of reducing agents involving samarium is well known. In this report, however, treatment of aromatic aldehydes with Cu(I)/Sm system produces benoins and/or benzils in good yields. A possible mechanism is proposed where Cu(I) not only activates the Sm metal but also promotes the dehydrogenation of the intermediates

  摘要 使用涉及钐的各种还原剂将醛还原偶联生成频哪醇是众所周知的。然而，在本报告中，用 Cu(I)/Sm 系统处理芳香醛以良好的收率产生了苯甲酸和/或苯甲醚。提出了一种可能的机制，其中 Cu(I) 不仅激活 Sm 金属，而且促进中间体的脱氢，在此过程中可能涉及 Cu(III) 物种。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• Samarium reagent-promoted formation of benzoins from diarylmethanones and DMF via a carbene rearrangement reaction
  作者：Yongjun Liu、Xiaoliang Xu、Yongmin Zhang

  DOI：10.1016/j.tet.2004.03.093

  日期：2004.5

  Prompted by samarium metal in DMF with TMSCl or iodine as an activator, or by SmI2/THF system, diarylmethanones react readily with DMF to afford benzoins in moderate to good yields via rearrangement of aryl groups. As for asymmetric diarylmethanones, products resulting from the migration of either aryl group were obtained, where the migration of aryl groups shows certain priority.

  在TMF1或碘作为活化剂的DMF中，用metal金属提示，或在SmI 2 / THF体系中，二芳基甲烷很容易与DMF反应，通过芳基的重排以中等至良好的收率得到苯偶姻。对于不对称的二芳基甲烷，获得了由任一芳基的迁移产生的产物，其中芳基的迁移表现出一定的优先权。
• Direct Formation of Benzoins from Diarylmethanones via a Rearrangement Reaction Promoted by Samarium Metal in DMF
  作者：Yongmin Zhang、Yongjun Liu、Xiaoliang Xu

  DOI：10.1055/s-2004-815408

  日期：——

  Diarylmethanones react readily with DMF when promoted by samarium metal in DMF with TMSCl or iodine as an activator, to afford benzoins in good to excellent yields via rearrangement of aryl groups. As for asymmetric diarylmethanones, products resulting from the migration of either aryl group were obtained, where the migration of aryl groups shows certain priority.

  当二芳基甲酮在 DMF 中以 TMSCl 或碘作为活化剂的钐金属促进时，二芳基甲酮很容易与 DMF 反应，通过芳基重排以良好至极好的产率提供安息香。对于不对称二芳基甲酮，得到任一芳基迁移的产物，其中芳基迁移具有一定的优先性。
• HITZEHÄRTENDE EPOXIDHARZZUSAMMENSETZUNG MIT HOHER LAGERSTABILITÄT
  申请人：SIKA TECHNOLOGY AG

  公开号：EP3476882A1

  公开（公告）日：2019-05-01

  Die vorliegende Erfindung betrifft einkomponentige hitzehärtende Epoxidharzzusammensetzungen, welche sich durch eine gute Lagerstabilität auszeichnen. Die Epoxidharzzusammensetzungen sind insbesondere geeignet für den Einsatz als Rohbauklebstoff und zur Herstellung von Strukturschäumen.

  本发明涉及单组分热固性环氧树脂组合物，其特点是具有良好的储存稳定性。这种环氧树脂组合物特别适合用作白坯粘合剂和生产结构泡沫。