5-(4-bromophenyl)-1,2,3,4-tetrahydrobenzo[a]phenanthridine | 24951-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(4-bromophenyl)-1,2,3,4-tetrahydrobenzo[a]phenanthridine
• CAS: 24951-95-9
• 化学式: C₂₃H₁₈BrN
• 分子量: 388.307
• InChiKey: RWOFLLVJKOWPJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(二苯基氨基)苯硼酸频那醇酯 、 5-(4-bromophenyl)-1,2,3,4-tetrahydrobenzo[a]phenanthridine 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 以50%的产率得到N,N-diphenyl-4′-(1,2,3,4-tetrahydrobenzo[a]phenanthridin-5-yl)[1,1′-biphenyl]-4-amine
  参考文献：
  名称：

  Improving of molecular planarity via tailoring alkyl chain within the molecules to enhance memory device performance

  摘要：

  DOI：

  10.1016/j.dyepig.2014.05.003
• 作为产物：
  描述：

  2-萘胺 在 盐酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 8.0h， 生成 5-(4-bromophenyl)-1,2,3,4-tetrahydrobenzo[a]phenanthridine
  参考文献：
  名称：

  摘要：

  Previously unknown derivatives of tetrahydro[a]phenanthridine containing annelated benzoquinoline and cyclohexene nuclei were prepared by condensation of azomethines of the 2-naphthylamine series with cyclohexanone. The possibility of synthesis of such compounds without preliminarily preparing Schiff bases was demonstrated. The effect of substituents in the aromatic ring of the azomethine on the yield of the target products was elucidated. The IR, UV, H-1 NMR, and mass spectra of the synthesized compounds were discussed.

  DOI：

  10.1023/a:1012355506689

文献信息

• An Efficient Method for the Synthesis of Benzo[<i>f</i>]quinoline and Benzo[<i>a</i>]phenanthridine Derivatives Catalyzed by Iodine by a Three-Component Reaction of Arenecarbaldehyde, Naphthalen-2-amine, and Cyclic Ketone
  作者：Xiang-Shan Wang、Qing Li、Chang-Sheng Yao、Shu-Jiang Tu

  DOI：10.1002/ejoc.200800287

  日期：2008.7

  A mild, efficient, and general method for the synthesis of benzo[f]quinoline and benzo[a]phenanthridine derivatives by a three-component reaction of arenecarbaldehyde, naphthalen-2-amine, and cyclic ketone using iodine as catalyst is described. A possible reaction mechanism for the formation of the product is proposed based on further experimental results.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  描述了一种温和、高效、通用的合成苯并 [f] 喹啉和苯并 [a] 菲啶衍生物的方法，该方法通过芳烃甲醛、萘-2-胺和环酮的三组分反应，以碘为催化剂。根据进一步的实验结果提出了形成该产物的可能反应机制。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• ——
  作者：N. G. Kozlov、L. I. Basalaeva

  DOI：10.1023/a:1012355506689

  日期：——

  Previously unknown derivatives of tetrahydro[a]phenanthridine containing annelated benzoquinoline and cyclohexene nuclei were prepared by condensation of azomethines of the 2-naphthylamine series with cyclohexanone. The possibility of synthesis of such compounds without preliminarily preparing Schiff bases was demonstrated. The effect of substituents in the aromatic ring of the azomethine on the yield of the target products was elucidated. The IR, UV, H-1 NMR, and mass spectra of the synthesized compounds were discussed.
• Improving of molecular planarity via tailoring alkyl chain within the molecules to enhance memory device performance
  作者：Rongcheng Bo、Hua Li、Hongzhang Liu、Hao Zhuang、Najun Li、Qingfeng Xu、Jianmei Lu、Lihua Wang

  DOI：10.1016/j.dyepig.2014.05.003

  日期：2014.10