N-(4-甲氧基-2-硝基苯基)氨基甲酸甲酯 | 29111-77-1

• 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-(4-甲氧基-2-硝基苯基)氨基甲酸甲酯
• 英文名称: methyl (4-methoxy-2-nitrophenyl)carbamate
• 英文别名: methyl 4-methoxy-2-nitrophenylcarbamate；Methyl-N-(4-methoxy-2-nitrophenyl)carbamat；methyl N-(4-methoxy-2-nitrophenyl)carbamate
• CAS: 29111-77-1
• 化学式: C₉H₁₀N₂O₅
• 分子量: 226.189
• InChiKey: VTATWAAUIITNPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-甲氧基-2-硝基苯基)氨基甲酸甲酯 、 3-溴丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以77%的产率得到methyl allyl(4-methoxy-2-nitrophenyl)carbamate
  参考文献：
  名称：

  The first intramolecular Heck–Matsuda reaction and its application in the syntheses of benzofurans and indoles

  摘要：

  In this Letter, we report, for the first time, the development of an efficient method for the intramolecular Heck reaction of arenediazonium salts in the synthesis of benzofuran and indole derivatives. In addition, this methodology allowed the synthesis of a series of dihydrobenzofuran acetic acid derivatives via a domino Heck-Matsuda coupling-carbonylation reaction. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.011
• 作为产物：
  描述：

  甲醇 、 N-苯基香豆甲酯 在 三氟化硼乙醚 、 硝酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 为溶剂， 反应 0.17h， 以47%的产率得到N-(4-甲氧基-2-硝基苯基)氨基甲酸甲酯
  参考文献：
  名称：

  Acylamino-Directed Specific Sequential Difunctionalizations of Anilides via Metal-Free Relay Reactions for p-Oxygen and o-Nitrogen Incorporation

  摘要：

  Novel acylamino-directed relay disubstitutions realize the sequential difunctionalizations of anilides (1) under mild and metal-free conditions for the first time. This [bis(trifluoroacetoxy)iodo]benzene (PIFA) and BF3 center dot Et2O promoted straightforward reaction produces a series of p-acetoxyl- or p-alkoxyl-o-nitro-N-arylamides (2), which are key scaffolds of various drugs, functional materials, and bioactive molecules. The flexibility with respect to the functional groups in these products affords this novel protocol excellent versatility for synthetic applications.

  DOI：

  10.1021/acs.joc.8b02636

文献信息

• Velikorodov, Russian Journal of Organic Chemistry, 2000, vol. 36, # 2, p. 233 - 239
  作者：Velikorodov

  DOI：——

  日期：——
• Acylamino-Directed Specific Sequential Difunctionalizations of Anilides via Metal-Free Relay Reactions for <i>p</i>-Oxygen and <i>o</i>-Nitrogen Incorporation
  作者：Yameng Wan、Zhiguo Zhang、Nana Ma、Jingjing Bi、Guisheng Zhang

  DOI：10.1021/acs.joc.8b02636

  日期：2019.1.18

  Novel acylamino-directed relay disubstitutions realize the sequential difunctionalizations of anilides (1) under mild and metal-free conditions for the first time. This [bis(trifluoroacetoxy)iodo]benzene (PIFA) and BF3 center dot Et2O promoted straightforward reaction produces a series of p-acetoxyl- or p-alkoxyl-o-nitro-N-arylamides (2), which are key scaffolds of various drugs, functional materials, and bioactive molecules. The flexibility with respect to the functional groups in these products affords this novel protocol excellent versatility for synthetic applications.
• The first intramolecular Heck–Matsuda reaction and its application in the syntheses of benzofurans and indoles
  作者：Fernanda A. Siqueira、Jason G. Taylor、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2010.02.011

  日期：2010.4

  In this Letter, we report, for the first time, the development of an efficient method for the intramolecular Heck reaction of arenediazonium salts in the synthesis of benzofuran and indole derivatives. In addition, this methodology allowed the synthesis of a series of dihydrobenzofuran acetic acid derivatives via a domino Heck-Matsuda coupling-carbonylation reaction. (c) 2010 Elsevier Ltd. All rights reserved.