2-(4-fluorophenyl)-2,3-dihydrophthalazine-1,4-dione | 361364-19-4

• 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: 2-(4-fluorophenyl)-2,3-dihydrophthalazine-1,4-dione
• 英文别名: Phthalazine-1,4(2H,3H)-dione, 2-(4-fluorophenyl)-；3-(4-fluorophenyl)-2H-phthalazine-1,4-dione
• CAS: 361364-19-4
• 化学式: C₁₄H₉FN₂O₂
• 分子量: 256.236
• InChiKey: KZWNYDILFWZJLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-2,3-dihydrophthalazine-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-fluorophenyl)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 、 4-氟苯肼盐酸盐 在 盐酸 作用下， 以 水 为溶剂， 反应 9.0h， 生成 2-(4-fluorophenyl)-2,3-dihydrophthalazine-1,4-dione
  参考文献：
  名称：

  Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones

  摘要：

  钌催化的简单、级联和一锅法合成了咖啉并环化二酮，通过对邻苯二酮/吡啶并咪唑酮的C-H活化。

  DOI：

  10.1039/c5cc09347c

文献信息

• Synthesis of cinnolines via Rh(<scp>iii</scp>)-catalysed dehydrogenative C–H/N–H functionalization: aggregation induced emission and cell imaging
  作者：Sivakalai Mayakrishnan、Yuvaraj Arun、Chandrasekar Balachandran、Nobuhiko Emi、Doraiswamy Muralidharan、Paramasivan Thirumalai Perumal

  DOI：10.1039/c5ob02045j

  日期：——

  Rhodium catalysed dehydrogenative C–H/N–H functionalization was developed to construct phthalazino[2,3-a]-/indazolo[1,2-a]cinnolines by reacting N-phenyl phthalazine/indazole with alkynes. The synthesized compounds exhibit prominent fluorescence properties in solid and aggregation states. Their application in cell imaging was investigated using various cancer cell lines.

  铑催化的脱氢CH- NH / NH官能团的开发是通过使N-苯基酞嗪/吲唑与炔烃反应来构建酞菁[ 2,3- a ]-/吲哚并[1,2- a ]辛啉。合成的化合物在固态和聚集态下显示出突出的荧光特性。使用各种癌细胞系研究了它们在细胞成像中的应用。
• Reducing-Agent-Free Convergent Synthesis of Hydroxyimino-Decorated Tetracyclic Fused Cinnolines via Rh^III-Catalyzed Annulation Using Nitroolefins
  作者：Pidiyara Karishma、Chikkagundagal K. Mahesha、Sanjay K. Mandal、Rajeev Sakhuja

  DOI：10.1021/acs.joc.0c02729

  日期：2021.2.5

  A mild Rh-catalyzed method was developed for the synthesis of hydroxyimino functionalized indazolo[1,2-a]cinnolines and phthalazino[2,3-a]cinnolines by reductive [4 + 2] annulation between 1-arylindazolones and 2-aryl-2,3-dihydrophthalazine-1,4-diones with varied nitroolefins. The targeted oxime decorated tetracyclic fused cinnolines were synthesized via sequential C–H activation/olefin insertion/reduction

  开发了一种温和的Rh催化方法，通过还原1-芳基吲唑酮和2-芳基-[4 + 2]环合反应，合成羟基亚氨基官能化的吲唑并[1,2- a ] cinnolines和邻苯并[2,3- a ] cinnolines。 2,3-二氢酞嗪-1,4-二酮与各种硝基烯烃。在无还原剂的条件下，通过连续的C–H活化/烯烃插入/还原反应，合成了目标肟肟修饰的四环稠合肉桂醛。
• Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones
  作者：Subramani Rajkumar、S. Antony Savarimuthu、Rajendran Senthil Kumaran、C. M. Nagaraja、Thirumanavelan Gandhi

  DOI：10.1039/c5cc09347c

  日期：——

  Ruthenium-catalyzed simple, cascade and one-pot synthesis of cinnoline-fused diones has been carried out by the C–H activation of phthalazinones/pyridazinones.

  钌催化的简单、级联和一锅法合成了咖啉并环化二酮，通过对邻苯二酮/吡啶并咪唑酮的C-H活化。
• Phthalazinone-Assisted C–H Amidation Using Dioxazolones Under Rh(III) Catalysis
  作者：Daeun Jeoung、Kunyoung Kim、Sang Hoon Han、Prithwish Ghosh、Suk Hun Lee、Saegun Kim、Won An、Hyung Sik Kim、Neeraj Kumar Mishra、In Su Kim

  DOI：10.1021/acs.joc.0c00352

  日期：2020.6.5

  agents and other entities. Herein, we report the phthalazinone-assisted carbon–nitrogen bond forming reaction using dioxazolones as robust amidation sources under Rh(III) catalysis. The broad functional group tolerance and complete site-selectivity are observed. Notably, a series of transformations of synthesized compounds into biologically relevant N-heterocycles demonstrates the applicability of the developed

  酞嗪酮衍生物的制备对于它们用作药物和其他实体至关重要。在此，我们报道了在Rh（III）催化下，使用二恶唑酮作为强酰胺化源的酞嗪酮辅助的碳-氮键形成反应。观察到宽泛的官能团耐受性和完全的位点选择性。值得注意的是，一系列合成化合物向生物学上相关的N杂环的转化证明了所开发方法的适用性。
• Ruthenium Catalyzed C−H Amidation and Carbocyclization using Isocyanates: An Access to Amidated 2‐phenylphthalazine‐1,4‐diones and Indazolo[1,2‐ <i>b</i> ]phthalazine‐triones
  作者：Pidiyara Karishma、Alisha Gogia、Sanjay K. Mandal、Rajeev Sakhuja

  DOI：10.1002/adsc.202001146

  日期：2021.2.2

  A direct carbocyclization of 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones is achieved using isocyanates as carbonyl source via Ru(II)‐catalyzed sequential ortho‐amidation followed by intramolecular nucleophilic substitution, delivering substituted indazolo[1,2‐b]phthalazine‐triones in good‐to‐excellent yields. For ortho‐substituted 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones, the corresponding amidated products

  使用异氰酸酯作为羰基来源，通过Ru（II）催化的顺序邻位酰胺化反应，然后进行分子内亲核取代，将取代的吲唑并[ 2,2-]-2-芳基-2,3-二氢酞嗪-1,4-二酮直接碳环化[1,2] ‐ b ]酞嗪三酮，收率良好。对于邻位取代的2-芳基-2,3-二氢邻苯二甲酸1,4-二酮，还可以通过修改反应参数以高收率分离出相应的酰胺化产物。异氰酸酯作为羰基来源的应用，在两个偶联配偶体上的高官能团耐受性以及合成的熔融和官能化邻苯二氮酮的多种化学转化是这项工作的重点。