4-硝基-N-[(1E)-3-苯基丙-2-烯-1-亚基]苯胺 | 15286-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-硝基-N-[(1E)-3-苯基丙-2-烯-1-亚基]苯胺
• 英文名称: cinnamaldehyde N-(4-nitrophenyl)imine
• 英文别名: N-Cinnamyliden-p-nitranilin；(E)-N-(4-nitrophenyl)-3-phenylprop-2-en-1-imine
• CAS: 15286-45-0；56110-09-9
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: RXBUYUMXXZKCCT-ZFCVXBDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-硝基-N-[(1E)-3-苯基丙-2-烯-1-亚基]苯胺 在 polymethylhydrosiloxane 作用下， 以 二氯甲烷 为溶剂， 生成 4-nitro-N-(3-phenylpropyl)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
• 作为产物：
  描述：

  反式肉桂醛 、 4-硝基苯胺 以 二氯甲烷 为溶剂， 生成 4-硝基-N-[(1E)-3-苯基丙-2-烯-1-亚基]苯胺
  参考文献：
  名称：

  通过亚磷酸的甲硅烷基酯合成有机磷化合物

  摘要：

  在室温下将原位产生的三甲基甲硅烷氧基磷（III）衍生物加到亚胺上，为α-氨基烷基磷酸酯和α-氨基烷基苯基次膦酸酯提供了温和的选择性和高产率的途径。异氰酸酯和碳二亚胺类似地反应，分别得到膦酰脲和膦酰胍，醛和酮的反应性低得多，氰化物是惰性的。

  DOI：

  10.1016/s0040-4020(01)87899-6

文献信息

• A new synthetic approach to the benzazole ring system. Synthesis and electrocyclic ring closure of dialkenyl and alkenyl-aryl substituted pyrroles, imidazoles and oxazoles
  作者：Janusz Moskal、Pens van Stralen、Djurre Postma、Albert M. van Leusen

  DOI：10.1016/s0040-4039(00)84479-2

  日期：1986.1

  An efficient synthesis is described of the substituted azoles referred to in the title, which are precursors of an equally successful new synthetic approach to indoles, benzimidazoles and benzoxazoles.

  描述了标题中所述的取代的吡咯的有效合成，它们是同等成功的吲哚，苯并咪唑和苯并恶唑的新合成方法的前体。
• Zayed, Salem E., Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 71, p. 193 - 196
  作者：Zayed, Salem E.

  DOI：——

  日期：——
• Synthesis of organophosphorus compounds via silyl esters of phosphorous acids
  作者：Kamyar Afarinkia、Charles W. Rees、John I.G. Cadogan

  DOI：10.1016/s0040-4020(01)87899-6

  日期：1990.1

  The addition of trimethylsilyloxy phosphorus (III)derivatives generated in situ to imines at room temperature provides a mild selective and high yielding route to α-aminoalkylphosphorate and α-aminoalkylphenylphosphinate esters. Isocyanates and carbodiimides react similarly to give phosphonoureas and phosphonoguarnidines respectively aldehydes and ketones are much less reactive and cyanides are inert

  在室温下将原位产生的三甲基甲硅烷氧基磷（III）衍生物加到亚胺上，为α-氨基烷基磷酸酯和α-氨基烷基苯基次膦酸酯提供了温和的选择性和高产率的途径。异氰酸酯和碳二亚胺类似地反应，分别得到膦酰脲和膦酰胍，醛和酮的反应性低得多，氰化物是惰性的。
• 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.