7,8-二氯-苯并[g]蝶啶-2,4(1H,3H)-二酮 | 58590-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 中文名称: 7,8-二氯-苯并[g]蝶啶-2,4(1H,3H)-二酮
• 英文名称: 7,8-dichloroalloxazine
• 英文别名: dichloroalloxazine；7,8-dichloro-1H-benzo[g]pteridine-2,4-dione；7,8-Dichlor-1H-benzo[g]pteridin-2,4-dion；7,8-dichloro-alloxazine；Benzo(g)pteridine-2,4(1H,3H)-dione, 7,8-dichloro-；7,8-dichloro-1H-benzo[g]pteridine-2,4-dione
• CAS: 58590-56-0
• 化学式: C₁₀H₄Cl₂N₄O₂
• 分子量: 283.073
• InChiKey: AXUFSJZRCPNZIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7,8-二氯-苯并[g]蝶啶-2,4(1H,3H)-二酮 在 硫酸 作用下， 反应 3.17h， 生成 ethyl 7,8-dichloro-imidazo-[1,2-a]-quinoxaline-2-carboxylate
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009
• 作为产物：
  描述：

  4,5-二氯邻苯二胺 、 四氧嘧啶 在 硼酸 作用下， 以 溶剂黄146 为溶剂， 以85%的产率得到7,8-二氯-苯并[g]蝶啶-2,4(1H,3H)-二酮
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009

文献信息

• Novel imidazoquinoxalines
  申请人：Roussel Uclaf

  公开号：US04254123A1

  公开（公告）日：1981-03-03

  Novel imidazoquinoxalines of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, --NH.sub.4, alkali metal, alkaline earth metal, magnesium, aluminum and non-toxic, pharmaceutically acceptable amines, X is selected from the group consisting of hydrogen, alkoxy of 1 to 5 carbon atoms and carbamoyl and Y and Z are individually selected from the group consisting of hydrogen and halogen and their non-toxic, pharmaceutically acceptable acid addition salts having anti-allergic activity and their preparation.

  该专利描述了一种公式为##STR1##的新型咪唑喹啉类化合物，其中R选自氢、1至5个碳原子的烷基、--NH.sub.4、碱金属、碱土金属、镁、铝和非毒性、药学上可接受的胺类；X选自氢、1至5个碳原子的烷氧基和氨基甲酰基；Y和Z各自选自氢和卤素，以及它们的非毒性、药学上可接受的酸盐，具有抗过敏活性。该专利还涉及了这些化合物的制备方法。
• A triangular prismatic hexanuclear iridium(<scp>iii</scp>) complex bridged by flavin analogues showing reversible redox processes
  作者：Yuji Inui、Motoo Shiro、Takahiro Kusukawa、Shunichi Fukuzumi、Takahiko Kojima

  DOI：10.1039/c2dt32535g

  日期：——

  spectroscopic and electrochemical measurements. The alloxazine ligands showed unprecedented coordination modes to link the six Ir(III) centres. The complex exhibited remarkable stability and reversible six-electron redox processes at the bridging alloxazine ligands in organic solvents. The first reversible reduction process occurred on each of three alloxazine ligands in 1 to produce a three-electron-reduced

  物[Ir 6（μ-alloCl 2 2-）3（CP *）6（OH）3 ]（PF 6）3（1），其具有7,8-二价阴离子dichloroalloxazine（alloCl 2 2-）作为桥连配体的合成和表征通过X射线晶体学，光谱学和电化学测量。别恶嗪配体显示出前所未有的配位模式来连接六个Ir（III）中心。该络合物在有机溶剂中桥联四恶嗪配体上显示出显着的稳定性和可逆的六电子氧化还原过程。第一个可逆的还原过程发生在1中的三个Alloxazine配体上以产生三电子还原的物种，物[Ir III 6的CP * 6（μ-alloCl 2 ˙ 3-）3（OH）3 ]，并观察作为表观一步还原过程在-0.65 V（VS Fc 0 / +）。在几乎相同的电位-0.78 V（vs . Fc 0 / +）下，记录了1中的三个Alloxazine配体的第二个可逆还原过程，得到六电子还原形式[Ir III 6 CP *
• Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts
  作者：Shuai Chen、Mohammad S. Hossain、Frank W. Foss

  DOI：10.1021/ol3010326

  日期：2012.6.1

  Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.
• Electron-Deficient Alloxazinium Salts: Efficient Organocatalysts of Mild and Chemoselective Sulfoxidations with Hydrogen Peroxide
  作者：Petra Ménová、Hana Dvořáková、Václav Eigner、Jiří Ludvík、Radek Cibulka

  DOI：10.1002/adsc.201300617

  日期：2013.11.25

  AbstractA series of substituted alloxazinium perchlorates has been prepared and tested as catalysts for the oxidation of sulfides to sulfoxides with hydrogen peroxide. The logarithms of the observed rate constants of thioanisole oxidation correlate with the Hammett σ constants of the substituents on the alloxazinium catalysts, as well as with their reduction potentials E0′ and their pKR+ values, representing the alloxazinium salt/pseudobase equilibrium. The stronger the electron‐withdrawing substituent, the more efficient is the alloxazinium catalyst. The alloxazinium salts with a cyano or trifluoromethyl group in position 8 proved to be the most efficient, operating at room temperature at small loadings, down to 0.1 mol%, achieving turnover number values of up to 640 and acceleration by a factor of 350 relative to the non‐catalyzed oxidation. The 8‐cyanoalloxazinium perchlorate was evaluated as the best catalyst; however, due to its relatively good accessibility, the 8‐(trifluoromethyl)alloxazinium perchlorate seems to be the catalyst of choice for sulfoxidations with hydrogen peroxide. It was successfully tested for the sulfoxidation of a series of aliphatic and aromatic sulfides on a preparative scale. It produced the corresponding sulfoxides in quantitative conversions and with high isolated yields (87–98%). No over‐oxidation to sulfone was ever observed.magnified image
• 144. A series of 9-dialkylaminoalkylisoalloxazines
  作者：R. B. Barlow、H. R. Ing

  DOI：10.1039/jr9500000713

  日期：——