9-(nitromethyl)anthracene | 61650-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(nitromethyl)anthracene
• CAS: 61650-95-1
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: ASYHQOYTTWVITK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(nitromethyl)anthracene 在 异氰酸苯酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到anthracene-9-carbonitrile N-oxide
  参考文献：
  名称：

  位阻芳基卤化物对硝基甲烷的芳基化

  摘要：

  开发了 Pd 催化空间位阻芳基卤化物与硝基甲烷交叉偶联的有效条件，得到相应的芳基硝基甲烷。证明了在这些条件下进行多硝基甲基化反应的机会，以及将所得产物用于合成二腈氧化物的机会。

  DOI：

  10.1007/s11172-022-3376-7
• 作为产物：
  描述：

  蒽-9-甲醛肟 在 三氟过氧乙酸 作用下， 生成 9-(nitromethyl)anthracene
  参考文献：
  名称：

  Homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in .alpha.-substituted and 10-substituted 9-methylanthracenes and their related radical anions

  摘要：

  Equilibrium acidities (pK(HA)), reduction potentials E(re)(HA), oxidation potentials E(ox)(HA), and oxidation potentials of the conjugate anions E(ox)(A-) have been measured in dimethylsulfoxide(DMSO) solution for 13 alpha-substituted 9-methylanthracenes (9-GCH2An) and 11 10-substituted 9-methylanthracenes (10-G-9-MeAn). The equilibrium acidities have been shown to be linearly correlated with Hammett sigma- constants. The similar rho- values for the linear correlations of pK(HA) Vs sigma- for 9-GCH2An (rho- = 13.8) and 10-G-9-MeAn (rho- = 14.2) demonstrate that the like substituents in 9-GCH2An and 10-G-9-MeAn have similar large effects on the equilibrium acidities. Suitable combinations of these equilibrium acidities with the reduction and oxidation potentials led to estimates of (a) the homolytic bond dissociation energies (BDE(HA)) of the acidic C-H bonds in 9-GCH2An and 10-G-9-MeAn, (b) the homolytic bond dissociation energies (BDE(HA.-)) of the acidic C-H bonds in 9-GCH2An.- and 10-G-9-MeAn.- radical anions, and (c) the radical cation acidities (pK(HA.+)) of the 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations. Introduction of alpha-CN and alpha-NO2 groups had opposite effects on the strengths (BDE(HA)) of the acidic C-H bonds in 9-GCH2An; the alpha-CN group decreased the BDE(HA) value by 2.5 kcal/mol and the alpha-NO2 increased the BDE(HA) value by 4.5 kcal/mol, but they both weakened the acidic C-H bonds in 9-GCH2An.- radical anions (by 10.6 and 12.5 kcal/mol, respectively). The BDEs of the acidic C-H bonds in 10-G-9-MeAn were estimated to be 81.3 +/- 1.3 kcal/mol and those in the corresponding radical anions were estimated to be 58.5 +/- 2.5 kcal/mol. The 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations are strongly acidic with the pK(HA.+) values estimated in the range of -5 to -11 pK(HA.+) units. Seven linear free energy relationships have been observed.

  DOI：

  10.1021/jo00063a025

文献信息

• SUZUKI HITOMI; YONEDA HAJIME; HANAFUSA TERUKIYO; SUGIYAMA TAKASHI, BULL. INST. CHEM. RES. KYOTO UNIV., 1976, 54, NO 3, 176-179
  作者：SUZUKI HITOMI、 YONEDA HAJIME、 HANAFUSA TERUKIYO、 SUGIYAMA TAKASHI

  DOI：——

  日期：——
• Homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in .alpha.-substituted and 10-substituted 9-methylanthracenes and their related radical anions
  作者：Xian Man Zhang、Frederick G. Bordwell、Joseph E. Bares、Jin Pei Cheng、Brian C. Petrie

  DOI：10.1021/jo00063a025

  日期：1993.5

  Equilibrium acidities (pK(HA)), reduction potentials E(re)(HA), oxidation potentials E(ox)(HA), and oxidation potentials of the conjugate anions E(ox)(A-) have been measured in dimethylsulfoxide(DMSO) solution for 13 alpha-substituted 9-methylanthracenes (9-GCH2An) and 11 10-substituted 9-methylanthracenes (10-G-9-MeAn). The equilibrium acidities have been shown to be linearly correlated with Hammett sigma- constants. The similar rho- values for the linear correlations of pK(HA) Vs sigma- for 9-GCH2An (rho- = 13.8) and 10-G-9-MeAn (rho- = 14.2) demonstrate that the like substituents in 9-GCH2An and 10-G-9-MeAn have similar large effects on the equilibrium acidities. Suitable combinations of these equilibrium acidities with the reduction and oxidation potentials led to estimates of (a) the homolytic bond dissociation energies (BDE(HA)) of the acidic C-H bonds in 9-GCH2An and 10-G-9-MeAn, (b) the homolytic bond dissociation energies (BDE(HA.-)) of the acidic C-H bonds in 9-GCH2An.- and 10-G-9-MeAn.- radical anions, and (c) the radical cation acidities (pK(HA.+)) of the 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations. Introduction of alpha-CN and alpha-NO2 groups had opposite effects on the strengths (BDE(HA)) of the acidic C-H bonds in 9-GCH2An; the alpha-CN group decreased the BDE(HA) value by 2.5 kcal/mol and the alpha-NO2 increased the BDE(HA) value by 4.5 kcal/mol, but they both weakened the acidic C-H bonds in 9-GCH2An.- radical anions (by 10.6 and 12.5 kcal/mol, respectively). The BDEs of the acidic C-H bonds in 10-G-9-MeAn were estimated to be 81.3 +/- 1.3 kcal/mol and those in the corresponding radical anions were estimated to be 58.5 +/- 2.5 kcal/mol. The 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations are strongly acidic with the pK(HA.+) values estimated in the range of -5 to -11 pK(HA.+) units. Seven linear free energy relationships have been observed.
• Arylation of nitromethane with sterically hindered aryl halides
  作者：M. A. Topchiy、A. N. Lysenko、M. A. Rasskazova、A. A. Ageshina、S. A. Rzhevskiy、L. I. Minaeva、M. S. Nechaev、A. F. Asachenko

  DOI：10.1007/s11172-022-3376-7

  日期：2022.1

  Efficient conditions for Pd-catalyzed cross-coupling of sterically hindered aryl halides with nitromethane were developed to give corresponding aryl nitromethanes. The opportunity to carry out the reaction of polynitromethylation under these conditions was demonstrated, as well as to use the obtained products in the synthesis of bisnitrile oxides.

  开发了 Pd 催化空间位阻芳基卤化物与硝基甲烷交叉偶联的有效条件，得到相应的芳基硝基甲烷。证明了在这些条件下进行多硝基甲基化反应的机会，以及将所得产物用于合成二腈氧化物的机会。