N-(4-nitrobenzylidene)-2-methylaniline | 17064-68-5

• 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: N-(4-nitrobenzylidene)-2-methylaniline
• 英文别名: N-<4-Nitro-benzyliden>-o-toluidin；4-Nitro-benzaldehyd-(2-methyl-anil)；N-(4-nitro-benzylidene)-o-toluidine；4-Nitro-benzaldehyd-o-tolylimin；N-(4-Nitro-benzyliden)-o-toluidin；4-Nitro-benzaldehyd-o-tolylimid；N-(2-methylphenyl)-1-(4-nitrophenyl)methanimine
• CAS: 17064-68-5
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: RQFFMSIFMJMNTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  N-(3-nitrobenzylidene)-O-toluidine 、 N-(4-nitrobenzylidene)-2-methylaniline 、 丁酮 在 碘 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 、
  参考文献：
  名称：

  Cross double Mannich reaction catalyzed by I2: Synthesis of highly substituted 4-piperidones

  摘要：

  Cross double Mannich reaction and tandem cyclization were achieved under iodine catalyzed conditions, yielding a series of highly substituted 4-piperidones. Among the possible diastereomers, only one diastereomer was isolated, which could be ascribed to the chair-like transition state in six-membered ring, in which all of the hindered groups are located in the pseudoequatorial orientation. (C) 2011 Xiao Dong Jia. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.12.008
• 作为产物：
  描述：

  对硝基苯甲醇 、 邻甲苯胺 在 nanosized zeolite Beta 、 air 作用下， 反应 24.0h， 以34%的产率得到N-(4-nitrobenzylidene)-2-methylaniline
  参考文献：
  名称：

  N-Alkylation of amines with alcohols over nanosized zeolite beta

  摘要：

  使用纳米尺寸的Beta沸石成功实现了胺与醇的直接N-烷基化反应，Beta沸石在其他传统沸石中显示出最高的催化活性。该方法具有多个优点，如环保性、适中至高产率以及简便的后续处理程序。催化剂可成功回收并重复使用，活性无明显损失，副产物仅为水。此外，通过使用纳米尺寸的Beta沸石，胺与2-、3-和4-硝基苄醇的串联反应也能高效制备亚胺。

  DOI：

  10.1039/c3gc41345d

文献信息

• Gawinecki, Ryszard, Polish Journal of Chemistry, 1987, vol. 61, # 4-6, p. 589 - 598
  作者：Gawinecki, Ryszard

  DOI：——

  日期：——
• Lowy; King, Journal of the American Chemical Society, 1921, vol. 43, p. 627
  作者：Lowy、King

  DOI：——

  日期：——
• N-Alkylation of amines with alcohols over nanosized zeolite beta
  作者：Marri Mahender Reddy、Macharla Arun Kumar、Peraka Swamy、Mameda Naresh、Kodumuri Srujana、Lanka Satyanarayana、Akula Venugopal、Nama Narender

  DOI：10.1039/c3gc41345d

  日期：——

  Direct N-alkylation of amines with alcohols was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcohols using nanosized zeolite beta.

  使用纳米尺寸的Beta沸石成功实现了胺与醇的直接N-烷基化反应，Beta沸石在其他传统沸石中显示出最高的催化活性。该方法具有多个优点，如环保性、适中至高产率以及简便的后续处理程序。催化剂可成功回收并重复使用，活性无明显损失，副产物仅为水。此外，通过使用纳米尺寸的Beta沸石，胺与2-、3-和4-硝基苄醇的串联反应也能高效制备亚胺。
• Cross double Mannich reaction catalyzed by I2: Synthesis of highly substituted 4-piperidones
  作者：Xiao Dong Jia、Xiang Ning Chen、Cong De Huo、Fang Fang Peng、Chang Qing、Xi Cun Wang

  DOI：10.1016/j.cclet.2011.12.008

  日期：2012.3

  Cross double Mannich reaction and tandem cyclization were achieved under iodine catalyzed conditions, yielding a series of highly substituted 4-piperidones. Among the possible diastereomers, only one diastereomer was isolated, which could be ascribed to the chair-like transition state in six-membered ring, in which all of the hindered groups are located in the pseudoequatorial orientation. (C) 2011 Xiao Dong Jia. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.