1,4-dihydro-2,6-dimethyl-3,5-bis<(phenylamino)carbonyl>-4-(p-methoxyphenyl)pyridine | 138571-08-1

• 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: 1,4-dihydro-2,6-dimethyl-3,5-bis<(phenylamino)carbonyl>-4-(p-methoxyphenyl)pyridine
• 英文别名: 4-(4-methoxyphenyl)-2,6-dimethyl-3-N,5-N-diphenyl-1,4-dihydropyridine-3,5-dicarboxamide
• CAS: 138571-08-1
• 化学式: C₂₈H₂₇N₃O₃
• 分子量: 453.541
• InChiKey: KCDXAATUWBEUEY-UHFFFAOYSA-N

物化性质

• 沸点：
  706.9±60.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 N-乙酰乙酰苯胺 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以91%的产率得到1,4-dihydro-2,6-dimethyl-3,5-bis<(phenylamino)carbonyl>-4-(p-methoxyphenyl)pyridine
  参考文献：
  名称：

  通过SO2-4 / SnO2催化的Hantzsch反应合成二氢吡啶的有效过程

  摘要：

  硫酸化的氧化锡（STO）被确立为通过Hantzsch反应一步合成二氢吡啶衍生物的令人敬佩的非均相催化剂。该合成方法主要在STO存在下作为非均相固体催化剂使用。STO催化的Hantzsch反应在80°C的乙腈中提供良好的收率（90–94％）。通过高分辨率质谱（HRMS），傅立叶变换红外光谱（FTIR），1 H和13 C-NMR以及光谱数据对合成的标题化合物进行表征和确认。

  DOI：

  10.1002/jccs.202000264

文献信息

• 1,4-Dihydropyridine charge control agents for electrostatographic toners and developers
  申请人：EASTMAN KODAK COMPANY

  公开号：EP1109070A2

  公开（公告）日：2001-06-20

  A charge control agent is disclosed selected from the group consisting of 1,4-dihydropyridines having the following general structure: where R1, R2, R3, R4, R5, X, and Z are defined in the specification. These compounds are useful in electrostatographic toners and developers.

  本发明公开了一种电荷控制剂，它选自具有以下一般结构的 1,4-二氢吡啶类： 其中 R1、R2、R3、R4、R5、X 和 Z 的定义见说明书。这些化合物适用于电致发光调色剂和显影剂。
• Zn-VCO3 hydrotalcite: A highly efficient and reusable heterogeneous catalyst for the Hantzsch dihydropyridine reaction
  作者：Ramakanth Pagadala、Suresh Maddila、Venkata D.B.C. Dasireddy、Sreekantha B. Jonnalagadda

  DOI：10.1016/j.catcom.2013.11.012

  日期：2014.2

  The Zn-VCO3 hydrotalcite was found to be an excellent solid catalyst for the one-pot synthesis of triphenylpyridine-3,5-dicarboxamide via Hantzsch reaction of acetoacetanilide, ammonium hydroxide and various aromatic aldehydes. The combinatorial syntheses were achieved for the first time using hydrotalcite as a heterogeneous catalyst. The catalyst was active for the Hantzsch reaction in water at 60 degrees C. The products were isolated in good yields (85-93%) with short reaction times (2-3 h). The resulting substituted dihydropyridines were characterized and confirmed by H-1 and C-13 NMR, FTIR, and HRMS spectral data and the solid catalyst was characterized by XRD, BET, SEM and TEM. The newly synthesized heterogeneous solid catalyst offers simple means for recovery and the isolated catalyst was reused for five rounds for the synthesis of compound 4a, without significant loss of catalytic activity. For all the other reactions carried out with the recycled catalyst, results were similar to with the fresh catalyst. (C) 2013 Elsevier B.V. All rights reserved.
• Reductions with NADH models. 3. The high reactivity of Hantzsch amides
  作者：Georges Gelbard、Jian Lin、Nathalie Roques

  DOI：10.1021/jo00032a035

  日期：1992.3

  Aromatic ketones and aldehydes are rapidly reduced to alcohols by various 1,4-dihydropyridines, several of which can be considered to be a model of the coenzyme NADH. The reducing agents bear amide groups and are closely related to Hantzsch esters. They exhibit the highest reactivity among NADH models so far described. In some cases, the rate and completeness of reduction by Hantzsch amides compare favorably with those of reduction by the usually employed metal hydrides.
• US6265127B1
  申请人：——

  公开号：US6265127B1

  公开（公告）日：2001-07-24
• An effective process for the synthesis of dihydropyridines via <scp> SO ₄ </scp> ⁻² / <scp> SnO ₂ </scp> ‐catalyzed Hantzsch reaction
  作者：Ramesh Goud Koduri、Ramakanth Pagadala、Ravi Varala、Satyanarayana Boodida

  DOI：10.1002/jccs.202000264

  日期：2021.2

  Sulfated tin oxide (STO) was established as an admirable heterogeneous catalyst for the single‐step synthesis of dihydropyridine derivatives via Hantzsch reaction. The synthetic method was mainly used in the presence of STO as a heterogeneous solid catalyst. STO‐catalyzed Hantzsch reaction afforded good yields (90–94%) in acetonitrile at 80°C. The synthesized titled compounds were characterized and

  硫酸化的氧化锡（STO）被确立为通过Hantzsch反应一步合成二氢吡啶衍生物的令人敬佩的非均相催化剂。该合成方法主要在STO存在下作为非均相固体催化剂使用。STO催化的Hantzsch反应在80°C的乙腈中提供良好的收率（90–94％）。通过高分辨率质谱（HRMS），傅立叶变换红外光谱（FTIR），1 H和13 C-NMR以及光谱数据对合成的标题化合物进行表征和确认。