N-cyclohexyl-2-nitrobenzamide | 1780-21-8

• 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-cyclohexyl-2-nitrobenzamide
• CAS: 1780-21-8
• 化学式: C₁₃H₁₆N₂O₃
• mdl: MFCD00578813
• 分子量: 248.282
• InChiKey: HVAPXQQNJGQXGW-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  432.2±28.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-2-nitrobenzamide 在 四羟基二硼 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以95%的产率得到2-cyclohexyl-1,2-dihydro-3H-indazol-3-one
  参考文献：
  名称：

  A B₂(OH)₄-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library

  摘要：

  Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B-2(OH)(4)-mediated reductive N-N bond formation is developed. This strategy features mild conditions, no request for a metal catalyst, and a wide scope for both aliphatic and aromatic amines. Meanwhile, this method was further successfully applied on DNA to construct indazolone cores for a DNA-encoded library. This will enable the production of a very attractive indazolone-cored library from simple amines and scaffolds, which will provide considerable diversity.

  DOI：

  10.1021/acs.orglett.0c02032
• 作为产物：
  描述：

  2-Cyclohexyl-3-(2-nitrophenyl)oxaziridine 在 ferric sulfate heptahydrate 、 sodium dodecyl-sulfate 作用下， 以 水 为溶剂， 反应 2.33h， 以86%的产率得到N-cyclohexyl-2-nitrobenzamide
  参考文献：
  名称：

  在水中和表面活性剂存在下，通过硫酸铁（III）催化经济地合成N-烷基苯甲酰胺的2-烷基-3-芳基恶唑烷的重排

  摘要：

  一种绿色温和的合成N-烷基苯甲酰胺的合成路线涉及从N-烷基胺和苯甲醛通过生态环保的一锅法合成2-烷基-3-芳基恶唑烷，然后将硫酸铁（III）催化重排为相应的酰胺。

  DOI：

  10.1039/c6gc03589b

文献信息

• Nickel-catalyzed reductive amidation of aryl-triazine ethers
  作者：Majid M. Heravi、Farhad Panahi、Nasser Iranpoor

  DOI：10.1039/c9cc08727c

  日期：——

  The reaction of activated phenolic compounds, 2,4,6-triaryloxy-1,3,5-triazine (aryl-triazine ethers), with various isocyanates or carbodiimides in the presence of a nickel pre-catalyst resulted in the synthesis of aryl amides in good to excellent yields.

  在镍预催化剂存在下，活化的酚类化合物2,4,6-三芳氧基-1,3,5-三嗪（芳基三嗪醚）与各种异氰酸酯或碳二亚胺的反应导致芳基酰胺的合成高产到高产。
• Synthesis and Crystal Structure of N-Cyclohexyl-2-Nitrobenzamide
  作者：Aamer Saeed、Shahid Hussain、Michael Bolte

  DOI：10.1007/s10870-010-9764-0

  日期：2010.11

  N-Cyclohexyl-2-nitrobenzamide was synthesized and characterized by spectroscopic data and X-ray diffraction analysis. It crystallizes at room temperature in the monoclinic space group P21/n with cell parameters a = 13.9913(10), b = 8.8475(4), c = 20.5627(15) Å, β = 93.278(6)°, V = 2541.3(3) Å3 and Z = 8. The structure was refined to final R1 = 0.0626 using all 4950 reflections. The crystal packing is stabilized by N–H⋯O hydrogen bonds. N-Cyclohexyl-2-nitrobenzamide was synthesized and characterized by spectroscopic data and X-ray diffraction analysis. It crystallizes at room temperature in the monoclinic space group P21/n with cell parameters a = 13.9913(10), b = 8.8475(4), c = 20.5627(15) Å, β = 93.278(6)°, V = 2541.3(3) Å3 and Z = 8. The structure was refined to final R1 = 0.0626 using all 4950 reflections. The crystal packing is stabilized by N–H⋯O hydrogen bonds.

  合成了 N-环己基-2-硝基苯甲酰胺，并通过光谱数据和 X 射线衍射分析进行了表征。它在室温下在单斜空间群 P21/n 中结晶，晶胞参数 a = 13.9913(10)、b = 8.8475(4)、c = 20.5627(15) Å、β = 93.278(6)°、V = 2541.3( 3) Å3 和 Z = 8。使用所有 4950 次反射将结构细化为最终 R1 = 0.0626。晶体堆积通过 N–H⋯O 氢键稳定。合成了 N-环己基-2-硝基苯甲酰胺，并通过光谱数据和 X 射线衍射分析进行了表征。它在室温下在单斜空间群 P21/n 中结晶，晶胞参数 a = 13.9913(10)、b = 8.8475(4)、c = 20.5627(15) Å、β = 93.278(6)°、V = 2541.3( 3) Å3 和 Z = 8。使用所有 4950 次反射将结构细化为最终 R1 = 0.0626。晶体堆积通过 N–H⋯O 氢键稳定。
• A Study on the Activation of Carboxylic Acids by Means of 2-Chloro-4,6-dimethoxy-1,3,5-triazine and 2-Chloro-4,6-diphenoxy-1,3,5-triazine
  作者：Z. J. Kamiński、P. Paneth、J. Rudziński

  DOI：10.1021/jo972020y

  日期：1998.6.1

  Activation of carboxylic function by means of 2-chloro-4,6-disubstituted-1,3,5-triazines 1 and 2 leading to triazine esters was found to be a multistep process with participation of quarternary triazinylammonium salts 3-6 as the intermediates, with the rate of reaction strongly dependent on the structure of the tertiary amine. The studies on alkylation of tertiary amines with CDMT revealed the two-step process A(N) + D-N, and zwitterionic addition product 9 was identified by H-1 NMR spectroscopy. Semiempirical modeling of the reaction as well as measured nitrogen and chlorine isotope effects also support this mechanism.
• ATTA-UR-RAHMAN; BASHA A.; WAHEED N.; AHMED S., TETRAHEDRON LETT. <TELE-AY>, 1976, NO 3, 219-222
  作者：ATTA-UR-RAHMAN、 BASHA A.、 WAHEED N.、 AHMED S.

  DOI：——

  日期：——
• Cu-Catalyzed Regioselective C–H Amination of 2<i>H</i>-Indazoles for the Synthesis of Indazole-Containing Indazol-3(2<i>H</i>)-ones
  作者：Lina Zhang、Hang Yan、Yueyue Fan、Xiande Luo、Yingqiao Pan、Yishu Liu、Yuepiao Cai、Qinqin Xia

  DOI：10.1021/acs.joc.3c00187

  日期：——