2-(p-tolyl)-1H-perimidine | 25110-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类 - 二氮杂萘
• 英文名称: 2-(p-tolyl)-1H-perimidine
• 英文别名: 2-(4-methylphenyl)-1H-perimidine
• CAS: 25110-47-8
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: VQHBDGIIHYIOAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(p-tolyl)-1H-perimidine 在 甲烷磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 生成 7-bromo-2-(p-tolyl)benzo[gh]perimidine
  参考文献：
  名称：

  非对称 2,7-二取代 1,3-二氮杂芘的合成，新的有前途的超分子化学对象

  摘要：

  许多非对称的 2,7-二取代的 1,3-二氮杂芘是通过 2-取代的 7-溴苯并[ gh ] 芘与苯基和戊基乙炔的 Sonogashira 交叉偶联合成的。开发了一种从 2-取代的 6-(5-bromo-3,4-dihydropyrimidin-4-yl)-1 H - perimidines直接一锅合成的方法。所提出的 1,3-二氮杂芘官能化方法可应用于超分子化学。

  DOI：

  10.1007/s10593-021-03016-z
• 作为产物：
  描述：

  环对甲基亚苄基丙二酸-2,2-丙二醇 、 1,8-二氨基萘 以 乙醇 为溶剂， 反应 5.5h， 以80%的产率得到2-(p-tolyl)-1H-perimidine
  参考文献：
  名称：

  使用亚芳基 Meldrum 酸作为芳基和氧化剂的来源合成 2-芳基-1H-苯并咪唑和 2-芳基-1H-perimidines

  摘要：

  亚芳基 Meldrum 酸被用作芳基的来源和氧化剂，用于通过与 1,2-苯二胺在回流乙醇中的缩合反应合成 2-芳基-1H-苯并咪唑，收率良好至高。亚芳基 Meldrum 的酸也被用作芳基的来源和氧化剂，用于通过与 1,8-二氨基萘在回流乙醇中的缩合反应以高产率合成 2-芳基-1H-脒。

  DOI：

  10.3184/174751918x15199196317528

文献信息

• A Cobalt Catalyst Permits the Direct Hydrogenative Synthesis of 1 <i>H</i> ‐Perimidines from a Dinitroarene and an Aldehyde
  作者：Tobias Schwob、Mirco Ade、Rhett Kempe

  DOI：10.1002/cssc.201900498

  日期：2019.7.5

  A new sustainable catalytic reaction, the synthesis of 1H‐ perimidines from a dinitroarene and an aldehyde in the presence of H2, was achieved. An earth‐abundant metal catalyst was developed to permit the efficient, highly chemoselective, and consecutive hydrogenation of dinitroarenes. The catalyst was reusable and easy to handle. The use of a specific Co complex and its pyrolysis at a certain temperature

  实现了一种新的可持续催化反应，即在H 2存在下由二硝基芳烃和醛合成1 H-亚氨基吡啶。开发了一种富含地球的金属催化剂，可实现对二硝基芳烃的高效，高度化学选择性和连续氢化。该催化剂是可重复使用的并且易于处理。使用特定的Co配合物及其在一定温度下的热解对于实现有机物转化的高活性至关重要。苯甲醛和脂肪醛可能会发生加氢缩合反应，因此可以容忍许多官能团，包括对碘敏感的芳基，腈基，烯烃和炔基等加氢敏感的例子。
• Synthesis of 7-Bromo-1,3-diazapyrenes
  作者：Alexander V. Aksenov、Stanisvlav V. Shcherbakov、Irina V. Lobach、Leonid G. Voskressensky、Michael Rubin

  DOI：10.1002/ejoc.201800703

  日期：2018.8.15

  Previously inaccessible 7‐bromo‐1,3‐diazapyrenes can be synthesized by an in‐melt peri‐cyclization of readily available 7‐(5‐bromo‐3,4‐dihydropyrimidin‐4‐yl)‐1H‐perimidines.

  以前无法获得的7-溴-1,3-二氮杂戊烯类可以通过容易获得的7-（5-溴-3,4-二氢嘧啶-4-基）-1H-嘧啶的熔体周环合成来合成。
• Novel perimidines, their preparation, formulations and use as immunosuppressives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0002906A2

  公开（公告）日：1979-07-11

  Novel 2-aryl-1H-perimidine compounds, which are useful as immunosuppressive agents, are described herein. The compounds are prepared by the condensation of 1,8-diaminonaphthalene with an appropriate acyl compound.

  本文描述了可用作免疫抑制剂的新型 2-芳基-1H-哌啶化合物。这些化合物是通过 1,8-二氨基萘与适当的酰基化合物缩合制备的。
• Magnetic Graphene Oxide Bearing ZrO₂ as a New Composite Catalyst for the Synthesis of 1<i>H</i>-Perimidines
  作者：M. A. Amrollahi、F. Ashayeri-Harati

  DOI：10.1080/00304948.2020.1761227

  日期：2020.7.3
• Design, synthesis and biological evaluation of novel perimidine o-quinone derivatives as non-intercalative topoisomerase II catalytic inhibitors
  作者：Du-Chao Zhou、Yu-Ting Lu、Yan-Wen Mai、Chen Zhang、Jie Xia、Pei-Fen Yao、Hong-Gen Wang、Shi-Liang Huang、Zhi-Shu Huang

  DOI：10.1016/j.bioorg.2019.103131

  日期：2019.10

  For the development of novel anticancer agents, we designed and synthesized a total of 37 perimidine o-quinone derivatives containing the o-quinone group at the A or B ring and different substituents (alkyl groups, aryl groups or heterocycles) at the C ring of the compounds. The structure-activity relationships (SARs) were established based on the cytotoxicity data of compounds from the HL-60, Huh7, Hct116, and Hela cell lines. The cytotoxicity results showed that most compounds exhibited potent cytotoxicity. In particular, compound b-12 showed the best anti-proliferative activity (IC50 <= 1 mu M) against four cancer cell lines and strong potency against the HL-60/MX2 (0.47 mu M) cell line, which is resistant to Topo II poisons. Further studies showed that b-12 exhibited potent Topo II alpha inhibitory activity (IC50 = 7.54 mu M) compared with Topo I, which acted as a class of non-intercalative Topo IIa catalytic inhibitor by inhibiting the ATP binding site of Topo II. Cell apoptosis and cell cycle assays confirmed that b-12 could induce the apoptosis of Huh7 cells in a dose-dependent manner.