6-bromo-3-methyl-1-phenylchromeno[2,3-c]pyrazol-4(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-bromo-3-methyl-1-phenylchromeno[2,3-c]pyrazol-4(1H)-one
• 英文别名: 6-Bromo-3-methyl-1-phenyl-1H-chromeno[2,3-c]pyrazol-4-one；6-bromo-3-methyl-1-phenylchromeno[2,3-c]pyrazol-4-one
• 化学式: C₁₇H₁₁BrN₂O₂
• 分子量: 355.191
• InChiKey: AIYAQGQJZMZRHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 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：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(4-bromophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 在 叔丁基过氧化氢 、 1,3-dibutyl-1H-benzo[d]-[1,2,3]triazol-3-ium bromide 作用下， 以 水 为溶剂， 反应 24.0h， 以68%的产率得到6-bromo-3-methyl-1-phenylchromeno[2,3-c]pyrazol-4(1H)-one
  参考文献：
  名称：

  Green Method for the Synthesis of Chromeno[2,3-c]pyrazol-4(1H)-ones through Ionic Liquid Promoted Directed Annulation of 5-(Aryloxy)-1H-pyrazole-4-carbaldehydes in Aqueous Media

  摘要：

  The first classical heterocyclic ionic liquid (IL) promoted C-H bond oxidant cross-doupling,reaction for the intramolecular annulation of 5-(aryloxy)-1H-pyrazole-4-carbal- dehydes to chromeno[2,37c]pyrazol-4(1H)-ones has been disclosed The promoter 1,3-dibutyl-1H-benzo[d]fl 2 3]- triazol-34-ium bromide can be easily recycled reused with the same efficacies for at least five cycles in aqueous medium The strategy works smoothly and provides applicable protocol to construct a Wide range of products.

  DOI：

  10.1021/acs.orglett.5b00033

文献信息

• Tricyclic Heteroaromatic Systems. Synthesis and A1 and A2a Adenosine Binding Activities of Some 1-Aryl-1,4-dihydro-3-methyl[1]benzopyrano[2,3-c]pyrazol-4-ones, 1-Aryl-4,9-dihydro-3-methyl-1H-pyrazolo[3,4-b]quinolin-4-ones, and 1-Aryl-1H-imidazo[4,5-b]quinoxalines
  作者：Daniela Catarzi、Lucia Cecchi、Vittoria Colotta、Guido Filacchioni、Claudia Martini、Paolo Tacchi、Antonio Lucacchini

  DOI：10.1021/jm00008a011

  日期：1995.4

  The syntheses and A1 and A2a adenosine binding activities of some new 1-aryl-1,4-dihydro-3-methyl[1]benzopyrano[2,3-c]pyrazol-4-ones, 1-aryl-4,9-dihydro-3-methyl-1H-pyrazolo[3,4-b]-quinolin-4-ones, and 1-aryl-1H-imidazo[4,5-b]quinoxalines are reported. Some compounds show A1 adenosine receptor affinity and selectivity. Structure-activity relationships on these new classes of adenosine receptor ligands

  一些新的1-芳基-1,4-二氢-3-甲基[1]苯并吡喃并[2,3-c]吡唑-4-酮，1-芳基-4,9-的合成以及A1和A2a腺苷结合活性据报道有二氢-3-甲基-1H-吡唑并[3，4-b]-喹啉-4-酮和1-芳基-1H-咪唑并[4，5-b]喹喔啉。一些化合物显示出A1腺苷受体亲和力和选择性。定义了这些新型腺苷受体配体上的构效关系。
• Copper-Catalyzed Tandem O-Arylation–Oxidative Cross Coupling: Synthesis of Chromone Fused Pyrazoles
  作者：Owk Obulesu、K. Harish Babu、Jagadeesh Babu Nanubolu、Surisetti Suresh

  DOI：10.1021/acs.joc.6b02890

  日期：2017.3.17

  Intermolecular tandem copper-catalyzed O-arylation-oxidative acylation (cross dehydrogenative coupling-CDC) has been developed under air as an oxidant. The reaction between 2,4-dihydro-3H-pyrazol-3-ones and ortho-halo aryl carboxaldehydes furnished the corresponding chromone fused pyrazoles, in a straightforward manner. The synthetic utility of the presented tandem catalysis has been demonstrated with the synthesis of an A(2)-subtype selective adenosine receptor antagonist in only two steps.[GRAPHICS]