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Synthesis of 13C4-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene
作者:Anhui Wu、Daiwang Xu、Ding Lu、Trevor M. Penning、Ian A. Blair、Ronald G. Harvey
DOI:10.1016/j.tet.2012.05.130
日期:2012.9
sensitive stable isotope dilution LC/MS method for analysis of BaP metabolites. We now report efficient syntheses of 13C4-BaP and the complete set of its 13C4-labelled oxidized metabolites needed as internal standards They include the metabolites not involved in carcinogenesis (Group A) and the metabolites implicated in initiation of cancer (Group B). The synthetic approach is novel, entailing use of Pd-catalyzed
多环芳烃 (PAH),例如苯并 [ a ] 芘 (B a P),是普遍存在的环境污染物,与导致肺癌有关。B a P 是烟草烟雾的一种成分,通过酶促转化为与 DNA 相互作用的活性形式。我们之前报道了一种用于分析 B a P 代谢物的灵敏的稳定同位素稀释 LC/MS 方法的开发。我们现在报告了13 C 4 -B a P 的有效合成及其完整的13 C 4标记氧化代谢物,需要作为内标。它们包括不参与致癌作用的代谢物(A 组))和与癌症发生有关的代谢物(B组)。该合成方法是新颖的,需要使用 Pd 催化的 Suzuki、Sonogashira 和 Hartwig 交叉偶联反应与 PtCl 2催化的炔属化合物环化反应相结合。这种合成方法需要更少的步骤,使用更温和的条件,并且产物分离比传统的 PAH 合成方法更简单。13 C 4 -B a P 和13 C 4 -B a P-8-ol的合成各只需要四步,并且13
Dimensional Matching of Polycyclic Aromatics with Rectangular Metallacycles: Insertion Modes Determined by [CH⋅⋅⋅π] Interactions
作者:Cristina Alvariño、Elena Pía、Marcos D. García、Víctor Blanco、Alberto Fernández、Carlos Peinador、José M. Quintela
DOI:10.1002/chem.201302165
日期:2013.11.4
set of polycyclicaromatic substrates (naphthalene, carbazol, pyrene, and benzo[a]pyrene), were characterized and studied in aqueous solution and the solid state. By taking into account the dimensions of both receptors and substrates, an excellent complementarity was found between the size of the receptors and their ability to complex a given substrate. Furthermore, this dimensionalmatching results
介绍了一个Pd II / Pt II双核受体家族,旨在使它们的腔长平稳增加(从7.46–13.78Å)。在水溶液和固态下,对它们的包合物与一组代表性的多环芳族底物(萘,咔唑,pyr和苯并[ a ] py)进行了表征和研究。通过考虑受体和底物的尺寸,在受体的大小与其复合给定底物的能力之间发现了极好的互补性。此外,在此特定维匹配结果结合取决于客户的建立稳定[C的能力模式 H⋅⋅⋅π]与主机交互。
Significant Enhancement in the Efficiency and Selectivity of Iron-Catalyzed Oxidative Cross-Coupling of Phenols by Fluoroalcohols
Significantenhancement of both the rate and the chemoselectivity of iron‐catalyzed oxidative coupling of phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP), 2,2,2‐trifluoroethanol (TFE), and 1‐phenyl‐2,2,2‐trifluoroethanol. The generality of this effect was examined for the cross‐coupling of phenols with arenes and polycyclic aromatic hydrocarbons (PAHs)
Regioselective arene homologation through rhenium-catalyzed deoxygenative aromatization of 7-oxabicyclo[2.2.1]hepta-2,5-dienes
作者:Masahito Murai、Takuya Ogita、Kazuhiko Takai
DOI:10.1039/c9cc00270g
日期:——
Combined use of oxorhenium catalysts with triphenyl phosphite as an oxygen acceptor allowed efficient deoxygenative aromatization of oxabicyclic dienes. The reaction proceeded under neutral conditions and was compatible with various functional groups. Combining this deoxygenation with regioselective bromination and trapping of the generated aryne with furan resulted in benzannulative π-extension at
A Convenient New Synthesis of Benzo[<i>a</i>]pyrene
作者:Ronald G. Harvey、Keunpoong Lim、Qing Dai
DOI:10.1021/jo030313n
日期:2004.2.1
A convenient newsynthesis of the ubiquitous environmental carcinogen benzo[a]pyrene (BaP) is described. In the key step, the method entails Suzuki coupling of naphthalene 2-boronic acid with 2-bromobenzene-1,3-dialdehyde and requires only three steps. It is considerably shorter and simpler than the older methods and provides BaP in higher overall yield.
描述了一种方便的新的普遍存在的环境致癌物苯并[ a ] re(BaP)的合成方法。在关键步骤中,该方法需要将萘2-硼酸与2-溴苯-1,3-二醛进行Suzuki偶联,仅需三个步骤。与旧方法相比,它明显更短,更简单,并且可以提供更高的总收率。