N-甲基-4-硝基-N-苯基苯甲酰胺 | 961-61-5

• 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: N-甲基-4-硝基-N-苯基苯甲酰胺
• 英文名称: N-methyl-N-phenyl-4-nitrobenzamide
• 英文别名: N-methyl-4-nitro-N-phenylbenzamide；N-Methyl-4-nitro-benzanilid；N-Methyl-4-nitrobenzanilide
• CAS: 961-61-5
• 化学式: C₁₄H₁₂N₂O₃
• mdl: MFCD00430508
• 分子量: 256.261
• InChiKey: MVDGHRIRJFXONZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 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：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-甲基-4-硝基-N-苯基苯甲酰胺 在 diphosphorus pentasulfide 作用下， 生成 N-methyl-p-nitrothiobenzanilide
  参考文献：
  名称：

  Movassagh, Barahman; Meibodi, Forhatosadat; Sobhani, Shahin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 6, p. 1296 - 1298

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯甲酸 在 三乙烯二胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 N-甲基-4-硝基-N-苯基苯甲酰胺
  参考文献：
  名称：

  Mechanism of decomposition of some carboxylic thiolcarbonic anhydrides

  摘要：

  DOI：

  10.1021/jo01269a039

文献信息

• An alternative and facile purification procedure of amidation and esterification reactions using a medium fluorous Mukaiyama reagent
  作者：Masato Matsugi、Misaki Suganuma、Shoko Yoshida、Shohei Hasebe、Yoko Kunda、Kotaro Hagihara、Sayaka Oka

  DOI：10.1016/j.tetlet.2008.09.016

  日期：2008.11

  convenient methodology for the separation of a fluorous by-product using fluorous chemistry is described. A Mukaiyama coupling reagent bearing a medium fluorous tag, between 40% and 60% fluorine by weight, can be effectively separated from non-fluorous components by increasing the water content of the crude reaction mixture and subsequent filtration. Additional fluorous solid phase extraction is not necessary

  描述了一种使用氟化学分离氟副产物的简便方法。通过增加粗反应混合物的水含量并随后过滤，可以有效地将氟含量在40％至60％之间的带有中等氟标签的Mukaiyama偶联剂与非氟组分有效地分离。不需要额外的氟固相萃取。
• KMnO4-mediated oxidative C N bond cleavage of tertiary amines: Synthesis of amides and sulfonamides
  作者：Zhang Zhang、Yong-Hong Liu、Xi Zhang、Xi-Cun Wang

  DOI：10.1016/j.tet.2019.03.047

  日期：2019.5

  KMnO4-mediated oxidative CN bond cleavage of tertiary amines producing secondary amine was introduced, which was trapped by electrophiles (acyl chloride and sulfonyl chloride) to form amides and sulfonamides. The reaction could take place at mild condition, tolerating a wide range of function groups and affording products in moderate to excellent yields.

  引入了KMnO 4介导的叔胺氧化C N键裂解生成仲胺的方法，该方法被亲电子试剂（酰氯和磺酰氯）捕获，形成酰胺和磺酰胺。反应可以在温和的条件下进行，可以耐受各种官能团，并提供中等至极好的收率的产物。
• TiCl₄-promoted desulfurization of thiocarbonyls and oxidation of sulfides in the presence of H₂O₂
  作者：Kiumars Bahrami、Mohammad M. Khodaei、Vida Shakibaian、Donya Khaledian、Behrooz H. Yousefi

  DOI：10.1080/17415993.2011.647915

  日期：2012.4.1

  TiCl4 proved to be a highly reactive reagent system for the desulfurization of thioamide and thioketone derivatives in excellent yields and short reaction times with high purity. Sulfides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases, these reactions are highly selective, simple, and clean, affording products in high yields and purity.

  H2O2 与 TiCl4 结合被证明是一种用于硫代酰胺和硫酮衍生物脱硫的高反应性试剂体系，收率高，反应时间短，纯度高。还发现硫化物在类似的反应条件下会氧化成砜。在大多数情况下，这些反应具有高度选择性、简单和清洁，可提供高产率和纯度的产品。
• A fluorous Mukaiyama coupling reagent for a concise condensation reaction: utility of medium-fluorous strategy
  作者：Yuya Sugiyama、Yuki Kurata、Yoko Kunda、Atsushi Miyazaki、Junko Matsui、Shuichi Nakamura、Hiromi Hamamoto、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tet.2012.03.034

  日期：2012.5

  condensation reactions using various fluorous Mukaiyama reagents, including a novel medium-fluorous strategy, is described. A Mukaiyama reagent bearing a medium-fluorous content tag, between 40 and 60% fluorine by weight, was prepared and examined in ester and amide-forming condensation reactions. At the end of the reactions, the fluorous pyridone by-product was effectively separated from non-fluorous components

  描述了使用各种含氟Mukaiyama试剂进行缩合反应的整个研究，包括新型中氟策略。制备了带有中等氟含量标签的Mukaiyama试剂，氟含量在40％至60％之间，并在形成酯和酰胺的缩合反应中进行了检测。在反应结束时，通过增加粗反应混合物的水含量并随后过滤沉淀物，有效地将氟吡啶酮副产物与非氟组分分离。还显示了带有氟标签的Mukaiyama试剂与其无氟标签的对应物相比，可显着提高反应速率。有趣的是，观察到氟链越长，Mukaiyama试剂的活性越高。
• New Heteroaromatic Azo Compounds Based on Pyridine, Isoxazole, and Benzothiazole for Efficient and Highly Selective Amidation and Mono-<i>N</i>-Benzylation of Amines under Mitsunobu Conditions
  作者：Nasser Iranpoor、Habib Firouzabadi、Dariush Khalili

  DOI：10.1246/bcsj.20090269

  日期：2010.8.15

  4,4′-Azopyridine (2c) is used in conjunction with triphenylphosphine for the efficient conversion of carboxylic acids into amides via Mitsunobu reaction with primary and secondary aliphatic and aromatic amines. The highly selective amidation of only primary aromatic amines with new heterogeneous azo compounds based on benzothiazole 2d and isoxazole 2e is also described. These azo compounds 2c–2e can also be applied for selective mono-N-benzylation of primary aromatic amines. The solid side product heteroaromatic hydrazines obtained under the developed Mitsunobu conditions are easily separated by simple filtration and can be reoxidized to azo compounds for further use.

  4,4′-偶氮吡啶（2c）与三苯基膦联合使用，可通过 Mitsunobu 反应高效地将羧酸转化为酰胺，适用于伯胺和仲胺、脂肪族胺和芳香族胺。还描述了基于苯并噻唑 2d 和新合成基于异恶唑 2e 的偶氮化合物的超高选择性的伯芳香胺酰胺化反应。这些偶氮化合物 2c-2e 还可用于选择性地单 N-苄基化伯芳香胺。在开发的 Mitsunobu 条件下得到的固体副产品杂芳香肼可以通过简单的过滤轻松分离，并且可以再氧化为偶氮化合物以供进一步使用。