1,10-trimethylenephenanthrene | 4389-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,10-trimethylenephenanthrene
• 英文别名: 5,6-Dihydro-4H-benzanthracen；5,6-dihydro-4H-benzo[de]anthracene；5,6-dihydro-4H-benzo[a]phenalene
• CAS: 4389-09-7
• 化学式: C₁₇H₁₄
• 分子量: 218.298
• InChiKey: VFZDNSWGNPSQLY-UHFFFAOYSA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  418.4±15.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,10-trimethylenephenanthrene 在 四(三苯基膦)钯 氢氧化钾 、 4 A molecular sieve 、 溴 、 cesium fluoride 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 二苯并(A,L)芘
  参考文献：
  名称：

  二苯并具有高度缩合成[ DEF，P ]屈（chrysene）及其12甲氧基衍生物，密钥前驱体对二苯并[的近端和最终致癌物的合成DEF，P ]屈

  摘要：

  二苯并[ def，p ]丙烯（DBC）（1）是迄今为止鉴定出的最具致突变性和毒性的多环芳烃。它的代谢活化导致反式-11,12-二羟基-11,12-二氢-DBC（2）进一步代谢为最终的代谢产物，反-反式-11,12-二羟基-13,14-环氧-11 ，12,13,14-tetrahydro-DBC（3），与DNA结合导致突变并最终诱导肿瘤。我们报告了合成DBC（1）及其12-甲氧基衍生物（12-methoxy-DBC）（13）（合成2和3的关键中间体）的简便方法，使用Suzuki交叉耦合方法。

  DOI：

  10.1021/jo0303822
• 作为产物：
  描述：

  2,3-二氢-1H-萉 在 platinum on activated charcoal 盐酸 、 三氯化铝 、 汞 、 锌 作用下， 生成 1,10-trimethylenephenanthrene
  参考文献：
  名称：

  Rahman,A. et al., Australian Journal of Chemistry, 1972, vol. 25, p. 1521 - 1527

  摘要：

  DOI：

文献信息

• The monomethyl and dimethyl derivatives of benzo[e]pyrene
  作者：Hongmee Lee、N. Shyamasundar、Ronald G. Harvey

  DOI：10.1016/s0040-4020(01)98957-4

  日期：1981.1

  claim16 that the analogous isomeric benzo[a]pyrene derivatives are principal products of reactions of this type is disproven. Synthesis of 3,6- and 4,5-dimethylbenzo[e]pyrene are also described. The structural assignments of all mono- and dimethyl benzo[e] pyrene products are supported by high resolution 270 MHz proton NMR spectra; the chemical shifts and coupling constants of all aromatic protons are

  描述了苯并[e] py的六种异构单甲基衍生物，1-，2-，3-，4-，9-和10-甲基苯并[e] py的先前未知的完整集合的便利合成。1-，2-和3-甲基苯并[e] py的合成是通过7H-苯并蒽（或其适当的1-Me衍生物）与1,3-双（二甲基氨基）三甲亚甲基高氯酸盐（或其1-Me）反应完成的衍生物），然后进行热电环闭合，并进行消除和芳构化。较早的索赔16证明类似的异构体苯并[a] py衍生物是这类反应的主要产物。还描述了3，6-和4，5-二甲基苯并[e] py的合成。高分辨率270 MHz质子NMR谱支持所有单和二甲基苯并[e] pyr产物的结构分配；所有芳族质子的化学位移和偶合常数均已完全赋值。
• Deacylation-aided C–H alkylative annulation through C–C cleavage of unstrained ketones
  作者：Xukai Zhou、Yan Xu、Guangbin Dong

  DOI：10.1038/s41929-021-00661-7

  日期：——

  on the aromatic core and a tethered alkyl moiety provides a straightforward approach to access these scaffolds; however, such a strategy is often hampered by the need of special reactive groups and/or less compatible cyclization conditions. It would be synthetically appealing if a common native functional group can be used as a handle to enable a general C–H annulation with diverse aromatic rings.

  芳烃和杂芳烃稠合环普遍存在于生物活性分子中。芳香核心上的 C-H 键和连接的烷基部分之间的直接环化提供了一种直接接近这些支架的方法；然而，这种策略通常会因需要特殊的反应基团和/或不太相容的环化条件而受到阻碍。如果可以使用一个共同的天然官能团作为手柄来实现具有不同芳香环的通用 C-H 环化，那将具有综合吸引力。在这里，我们展示了一种脱酰基环化策略，用于从线性简单酮前体制备多种芳族稠环。该反应首先通过前芳族中间体均裂酮α C-C 键，然后是自由基介导的脱氢环化。
• Benzylic oxidation with 2,3-dichloro-5,6-dicyanobenzoquinone in aqueous media. A convenient synthesis of aryl ketones and aldehydes
  作者：Hongmee Lee、Ronald G. Harvey

  DOI：10.1021/jo00153a030

  日期：1983.3
• Chemistry of the Oxo and Related Reactions. IV. Reductions in the Aromatic Series¹
  作者：Irving Wender、Harold Greenfield、Milton Orchin

  DOI：10.1021/ja01150a069

  日期：1951.6
• Pupils' views of the role and value of the science curriculum: A focus-group study
  作者：Jonathan Osborne、Sue Collins

  DOI：10.1080/09500690010006518

  日期：2001.5

  Pupils' perceptions of their experience of school science have rarely been investigated. The aim of the research reported in this paper, therefore, was to document the range of views that pupils held about the school science curriculum, the aspects they found either interesting and/or valuable, and their views about its future content. As such, the research aimed to articulate their views as a contribution to the debate about the future form and function of the school science curriculum. The method adopted to elicit their views was to use focus groups-a methodology that has not been extensively used in the science education research. Reported here are the findings from 20 focus groups conducted with 144 16-year-old pupils in London, Leeds and Birmingham, split both by gender and whether the pupils intended to continue, or not, with the study of science post-16. The findings of this research offer a window into pupils' perspective of school science revealing both their discontents and satisfaction with the existing curriculum. On the negative side, many pupils perceived school science to be a subject dominated by content with too much repetition and too little challenge. From a more positive perspective, pupils saw the study of science as important and were engaged by topics where they could perceive an immediate relevance, practical work, material that was challenging and high-quality teaching. The implications of these findings and the insights they provide for curriculum policy and school science curricula are discussed.

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