1,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanobenzoquinoxaline | 6058-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanobenzoquinoxaline
• 英文别名: camphorquinoxaline；1,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methano-phenazine；1,11,11-Trimethyl-1,2,3,4-tetrahydro-1,4-methano-phenazin；1-Methyl-1,2,3,4-tetrahydro-1,4-dimethylmethano-phenazin；Bornen-<2,3-b>chinoxalin；(+/-)-Camphanochinoxalin；1,11,11-Trimethyl-1,2,3,4-tetrahydro-1,4-methanophenazine；1,15,15-trimethyl-3,10-diazatetracyclo[10.2.1.02,11.04,9]pentadeca-2,4,6,8,10-pentaene
• CAS: 6058-27-1
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: NGUAUQBJYSZURH-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C
• 沸点：
  352.3±37.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanobenzoquinoxaline 、 单过氧邻苯二甲酸 以55%的产率得到
  参考文献：
  名称：

  HAHN W. E.; CEBULSKA Z., ROCZ. CHEM. , 1975, 49, NO 5, 973-978

  摘要：

  DOI：
• 作为产物：
  描述：

  樟脑醌 、 邻苯二胺 以 甲醇 为溶剂， 生成 1,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanobenzoquinoxaline
  参考文献：
  名称：

  刚性双齿氮配体的合成和表征，以及与二价钯配位的一些实例。双（对甲苯胺）和甲基氯[双（o， o'-二异丙基苯基-亚氨基）]钯（II）的X射线晶体结构†

  摘要：

  描述了刚性双齿氮配体双-（苯基亚氨基）樟脑（Ph-BIC）和一系列双（芳基））啶（Ar-BIAN）的合成和表征。这些配体是在樟脑醌或苯醌与相应的（取代的）苯胺在ZnCl 2或NiBr 2的存在下反应，然后在随后的步骤中除去金属盐而合成的。NDDO在p Tol- BIAN上的计算表明，该配体的电子性质与开链类似物Ph-DAB（DAB = 1,4-diaza-1,3-butadiene）相当。Ar-BIAN配体的亚胺N原子上的芳族基团定向在双（亚氨基）ac基平面之外，导致形成顺式和反式为异构体的邻位-取代的衍生物ö -MeC 6 ħ 4 -BIAN和OI PRC 6 ħ 4 -BIAN。在溶液中观察到这些配体的一种异构体，但是与Pd（Me）Cl片段配位后，由于形成了两种异构体，因此同时存在顺式和反式形式。此外，描述了尝试合成双（异丙基亚氨基）环己烷，但是发现形成了互变异构的亚胺-烯胺化合物，其

  DOI：

  10.1002/recl.19941130204

文献信息

• Synthesis and Characterization of Camphorimine Au(I) Complexes with a Remarkably High Antibacterial Activity towards B. contaminans and P. aeruginosa
  作者：Joana P. Costa、Sílvia A. Sousa、Catarina Soeiro、Jorge H. Leitão、Adelino M. Galvão、Fernanda Marques、M. Fernanda N. N. Carvalho

  DOI：10.3390/antibiotics10101272

  日期：——

  Fourteen new camphorimine Au(I) complexes were synthesized and characterized by spectroscopic (NMR, FTIR) and elemental analysis. The structural arrangement of three selected examples were computed by Density Functional Theory (DFT) showing that the complexes essentially keep the AuI-CN} unit. The Minimum Inhibition Concentrations (MIC) were assessed for all complexes showing that they are active towards the Gram-negative strains E. coli ATCC25922, P. aeruginosa 477, and B. contaminans IST408 and the Gram-positive strain S. aureus Newman. The complexes display very high activity towards P. aeruginosa 477 and B. contaminans IST408 with selectivity towards B. contaminans. An inverse correlation between the MIC values and the gold content was found for B. contaminans and P. aeruginosa. However, plots of MIC values and Au content for P. aeruginosa 477 and B. contaminans IST408 follow distinct trends. No clear relationship could be established between the MIC values and the redox potentials of the complexes measured by cyclic voltammetry. The MIC values are essentially independent of the redox potentials either cathodic or anodic. The complexes K3[Au(CN)2}3(A4L)] (8, Y = m-OHC6H4) and K3[Au(CN)2}3(B2L)]·3H2O (14, Z = p-C6H4) display the lower MIC values for the two strains. In normal fibroblast cells, the IC50 values for the complexes are ca. one order of magnitude lower than their MIC values, although higher than that of the precursor KAu(CN)2.

  合成了14个新的松香胺Au(I)配合物，并通过光谱学（NMR，FTIR）和元素分析进行了表征。通过密度泛函理论（DFT）计算，选取了三个样品的结构排列，显示配合物基本保持AuI-CN}单元。评估了所有配合物的最小抑菌浓度（MIC），显示它们对革兰氏阴性菌E. coli ATCC25922、P. aeruginosa 477和B. contaminans IST408以及革兰氏阳性菌S. aureus Newman都具有活性。配合物对P. aeruginosa 477和B. contaminans IST408表现出非常高的活性，对B. contaminans具有选择性。对于B. contaminans和P. aeruginosa，MIC值与金含量呈反相关。然而，对于P. aeruginosa 477和B. contaminans IST408的MIC值和金含量的图表遵循不同的趋势。通过循环伏安法测量的配合物的氧化还原电位与MIC值之间没有明显的关系。MIC值无论是阴极还是阳极电位都基本独立。配合物K3[Au(CN)2}3(A4L)]（8，Y = m-OH ）和K3[Au(CN)2}3(B2L)]·3H2O（14，Z = p-C6H4）对两种菌株的MIC值较低。在正常成纤维细胞中，配合物的IC50值约比它们的MIC值低一个数量级，但高于前体KAu(CN)2的IC50值。
• Synthesis of Quinoxalines Under Focussed Microwave Irradiation
  作者：Didier Villemin、Beno[icaron]t Martin

  DOI：10.1080/00397919508011789

  日期：1995.8

  Quinoxalines were obtained by the condensation of alpha-diones with o-diaminobenzenes without solvent under focussed microwave irradiation.
• Synthesis, characterization and study of the catalytic properties of Zn(II) camphor derived complexes
  作者：Tiago A. Fernandes、Ana M. Ferraria、Adelino M. Galvão、Ana M. Botelho do Rego、Ana C.M. Suárez、M.Fernanda N.N. Carvalho

  DOI：10.1016/j.jorganchem.2013.10.040

  日期：2014.6

  Zinc(II) complexes of general formula [ZnX2(YNC10H14O)], [ZnX2(YNC10H13NSO2)], [ZnX2(H2NNC10H14O)(2)], [ZnX2}(2)(YNC10H14O)] and [ZnX2}(2)(YNC10H13NSO2)] were obtained from zinc halides (chloride or bromide) by reaction with the suitable camphor ligands.In most of the complexes, the camphor ligands remain unchanged upon coordination, except in [Zn(MeNNC10H14O)}(2)(mu-Cl)(2)] where proton loss from MeHNNC10H14O occurs. The new complexes and camphor derivatives were characterized by IR, NMR (H-1, C-13H}, DEPT, 2D) and elemental analysis. In some cases the surface composition was studied by X-ray photoelectron spectroscopy (XPS) and imaged by Scanning Electron Microscopy (SEM). Images of [ZnCl2(Me2NNC10H14O)] and [ZnCl2(Me2NNC10H13NSO2)] obtained by SEM show the solid particles have tubular structures capped in one or both extremities. The coordination of THF in [ZnCl2(YNC10H14O) THF] was confirmed by X-ray diffraction analysis. The camphor derivatives YNC10H14NSO2 (Y = NMe2; NHMe) and p-C6H4(NC10H14O)(2) were structurally characterized by X-ray diffraction analysis.The ability of selected Zn(II) camphor complexes to catalyse the cyclization of 4-pentyn-1-ol was evaluated showing that the binuclear complex [ZnX2}(2)(YNC10H14O)] performs better than the mononuclear Zn(II) complexes. (C) 2013 Elsevier B.V. All rights reserve.
• Singh; Mazumder, Journal of the Chemical Society, 1919, vol. 115, p. 573
  作者：Singh、Mazumder

  DOI：——

  日期：——