3-(4-tert-butylphenyl)-2H-phthalazine-1,4-dione | 1259300-53-2

• 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: 3-(4-tert-butylphenyl)-2H-phthalazine-1,4-dione
• CAS: 1259300-53-2
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: NCXBLWBCMBVIIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-tert-butylphenyl)-2H-phthalazine-1,4-dione 在 三溴氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 4-Bromo-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one
  参考文献：
  名称：

  Phthalazinone Pyrazoles as Potent, Selective, and Orally Bioavailable Inhibitors of Aurora-A Kinase

  摘要：

  The inhibition of Aurora kinases in order to arrest mitosis and subsequently inhibit tumor growth via apoptosis of proliferating cells has generated significant discussion within the literature. We report a novel class of Aurora kinase inhibitors based upon a phthalazinone pyrazole scaffold. The development of the phthalazinone template resulted in a potent Aurora-A selective series of compounds (typically >1000-fold selectivity over Aurora-B) that display good pharmacological profiles with significantly improved oral bioavailability compared to the well studied Aurora inhibitor VX-680.

  DOI：

  10.1021/jm101346r
• 作为产物：
  描述：

  苯酐 、 对特丁基苯肼盐酸盐 在 溶剂黄146 作用下， 反应 2.0h， 生成 3-(4-tert-butylphenyl)-2H-phthalazine-1,4-dione
  参考文献：
  名称：

  Phthalazinone Pyrazoles as Potent, Selective, and Orally Bioavailable Inhibitors of Aurora-A Kinase

  摘要：

  The inhibition of Aurora kinases in order to arrest mitosis and subsequently inhibit tumor growth via apoptosis of proliferating cells has generated significant discussion within the literature. We report a novel class of Aurora kinase inhibitors based upon a phthalazinone pyrazole scaffold. The development of the phthalazinone template resulted in a potent Aurora-A selective series of compounds (typically >1000-fold selectivity over Aurora-B) that display good pharmacological profiles with significantly improved oral bioavailability compared to the well studied Aurora inhibitor VX-680.

  DOI：

  10.1021/jm101346r

文献信息

• Rhodium(<scp>iii</scp>)-catalyzed C–H alkylation of arylhydrophthalazinediones with α-Cl ketones as sp³-carbon alkylated agents
  作者：He Li、Haichun Gu、Ning Xu、Ye Lu、Xinxin Jin、Jiaqi Li、Hongyu Guo、Dawei Cao、Jinglin Liu

  DOI：10.1039/d3ob00091e

  日期：——

  A Rh(III)-catalyzed C–H bond direct alkylation between 2-arylphthalazine-1,4-diones and α-Cl ketones, which are sp3-carbon synthons, under mild conditions has been disclosed. The corresponding phthalazine derivatives are readily obtained in moderate to excellent yields with a wide range of substrates and high functional group tolerance. The practicality and utility of this method are demonstrated by

  已公开了在温和条件下2-芳基酞嗪-1,4-二酮和 α-Cl 酮（sp3-碳合成子）之间的 Rh(III) 催化的 C-H 键直接烷基化反应。相应的酞嗪衍生物很容易以中等到极好的产率获得，具有广泛的底物范围和高官能团耐受性。产物的衍生化证明了该方法的实用性和实用性。
• Accessing oxy-functionalized N-heterocycles through rose bengal and TBHP integrated photoredox C(sp³)–O cross-coupling
  作者：Rahul Dev Mandal、Moumita Saha、Asish R. Das

  DOI：10.1039/d2ob00381c

  日期：——

  Herein, we report a practical and simple mono- and di-C(sp3)–O cross-coupling of tautomerizable N-heterocycles (dihydrophthalazine-1,4-diones, pyridone, quinoxalinone and pyrimidinone) with ketones, β-dicarbonyl compounds and nitroalkane, leading to substituted imidate derivatives under visible-light conditions. The combination of rose bengal as the photocatalyst and TBHP enables sustainable reaction

  在此，我们报告了一种实用且简单的单-和双-C(sp 3)–O 可互变异构的 N-杂环（二氢酞嗪-1,4-二酮、吡啶酮、喹喔啉酮和嘧啶酮）与酮、β-二羰基化合物和硝基烷烃的交叉偶联，在可见光条件下产生取代的酰亚胺衍生物。玫瑰红作为光催化剂和 TBHP 的组合实现了可持续的反应条件、操作简单性、高化学和区域选择性以及出色的产率（高达 94%）、良好的官能团耐受性和底物通用性。在不对称酮的情况下，较少取代的末端被选择性地官能化。di-C-O 偶联产物通常由在反应部位含有三个可烯醇化“H”的酮获得，而具有两个可烯醇化“H”的酮仅提供单一偶联产物。自由基抑制实验揭示了自由基途径参与这种偶联策略。耦合产品也被放大到克级，为进一步的功能化提供了空间通过C-H 键活化。
• Phthalazinone Pyrazoles as Potent, Selective, and Orally Bioavailable Inhibitors of Aurora-A Kinase
  作者：Michael E. Prime、Stephen M. Courtney、Frederick A. Brookfield、Richard W. Marston、Victoria Walker、Justin Warne、Andrew E. Boyd、Norman A. Kairies、Wolfgang von der Saal、Anja Limberg、Guy Georges、Richard A. Engh、Bernhard Goller、Petra Rueger、Matthias Rueth

  DOI：10.1021/jm101346r

  日期：2011.1.13

  The inhibition of Aurora kinases in order to arrest mitosis and subsequently inhibit tumor growth via apoptosis of proliferating cells has generated significant discussion within the literature. We report a novel class of Aurora kinase inhibitors based upon a phthalazinone pyrazole scaffold. The development of the phthalazinone template resulted in a potent Aurora-A selective series of compounds (typically >1000-fold selectivity over Aurora-B) that display good pharmacological profiles with significantly improved oral bioavailability compared to the well studied Aurora inhibitor VX-680.