4-nitro-N-(pyridin-4-ylmethyl)aniline | 749872-65-9

• 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: 4-nitro-N-(pyridin-4-ylmethyl)aniline
• 英文别名: N-(4-picolyl)-4-nitroaniline；PINA
• CAS: 749872-65-9
• 化学式: C₁₂H₁₁N₃O₂
• mdl: MFCD05271682
• 分子量: 229.238
• InChiKey: IRAQCAZDHFQRFW-UHFFFAOYSA-N

物化性质

• 熔点：
  144-147 °C
• 沸点：
  424.3±30.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)
• 溶解度：
  >34.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitro-N-(pyridin-4-ylmethyl)aniline 、 zinc(II) propionate 以 甲醇 为溶剂， 以80.6%的产率得到Zn(N-(4-picolyl)-4-nitroaniline)2(propionato)2
  参考文献：
  名称：

  通过锌（II）络合组装的远程功能化非手性NLO-phor的SHG活性晶体。

  摘要：

  在吡啶衍生的4-硝基苯胺的基础上，开发了一种非手性的非线性光学发色团，其具有可作为配体的“远程官能团”。这些分子通过与简单的非手性锌（II）盐和由抗衡离子介导的H键网络络合而组装，以生成显示光学二次谐波（SHG）的非中心对称材料。确定了新配合物的晶体结构。抗衡离子强烈影响配体的取向和晶格结构。研究了微晶材料的SHG。使用分子和分子簇的超极化性的半经验量子化学估计来合理化结构和SHG之间的相关性。金属络合物在分子组装中起着重要作用，但对SHG的影响很小，因此可以简化从分子反应方面分析整体性质的过程。因此，通过金属离子络合的远程官能化分子的组织为二次NLO材料的合理设计提供了一种方便的方法。

  DOI：

  10.1021/ic061145v
• 作为产物：
  描述：

  4-nitro-N-pyridin-4-ylmethylene-aniline 在 polymethylhydrosiloxane 作用下， 以 二氯甲烷 为溶剂， 生成 4-nitro-N-(pyridin-4-ylmethyl)aniline
  参考文献：
  名称：

  Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions

  摘要：

  Polymethylhydrosiloxine (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of(het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was Successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Bronsted acid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.048

文献信息

• Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions
  作者：Jay P. Patel、An-Hu Li、Hanqing Dong、Vijaya L. Korlipara、Mark J. Mulvihill

  DOI：10.1016/j.tetlet.2009.08.048

  日期：2009.11

  Polymethylhydrosiloxine (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of(het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was Successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Bronsted acid. (C) 2009 Elsevier Ltd. All rights reserved.
• SHG Active Crystals of a Remote Functionalized Achiral NLO-phore Assembled through Zinc(II) Complexation
  作者：M. Jaya Prakash、T. P. Radhakrishnan

  DOI：10.1021/ic061145v

  日期：2006.11.1

  optical chromophore with a "remote functionality" that can act as a ligand is developed on the basis of 4-nitroaniline derivatized with pyridine. The molecules are assembled through complexation with simple achiral zinc(II) salts and the H-bond network mediated by the counterions, to generate noncentrosymmetric materials exhibiting optical second harmonic generation (SHG). The crystal structures of the

  在吡啶衍生的4-硝基苯胺的基础上，开发了一种非手性的非线性光学发色团，其具有可作为配体的“远程官能团”。这些分子通过与简单的非手性锌（II）盐和由抗衡离子介导的H键网络络合而组装，以生成显示光学二次谐波（SHG）的非中心对称材料。确定了新配合物的晶体结构。抗衡离子强烈影响配体的取向和晶格结构。研究了微晶材料的SHG。使用分子和分子簇的超极化性的半经验量子化学估计来合理化结构和SHG之间的相关性。金属络合物在分子组装中起着重要作用，但对SHG的影响很小，因此可以简化从分子反应方面分析整体性质的过程。因此，通过金属离子络合的远程官能化分子的组织为二次NLO材料的合理设计提供了一种方便的方法。