2,6-dimethyl-3-phenyl-4H-pyran-4-one | 40122-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,6-dimethyl-3-phenyl-4H-pyran-4-one
• 英文别名: 2,6-Dimethyl-3-phenylpyran-4-one
• CAS: 40122-80-3
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: RMDLFJOOIBPSAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-3-phenyl-4H-pyran-4-one 在 ammonium hydroxide 、 溴 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 74.0h， 生成 3-bromo-4-chloro-2,6-dimethyl-5-phenylpyridine
  参考文献：
  名称：

  A Suzuki-Miyaura Approach to a Series of Forensically Relevant Pyridines

  摘要：

  本文介绍了制备十六种具有重要法医意义的 3,5 二取代 2,4- 和 2,6 二甲基吡啶的简便通用方法。一系列环取代的苯硼酸与 3,5-二溴-2,4-二甲基吡啶和 3,5-二溴-2,6-二甲基吡啶之间的铃木交叉偶联反应被用作关键步骤。

  DOI：

  10.1055/s-2006-942535
• 作为产物：
  描述：

  乙酸酐 、 苯基丙酮 在 PPA 作用下， 反应 0.5h， 生成 2,6-dimethyl-3-phenyl-4H-pyran-4-one
  参考文献：
  名称：

  4-吡啶酮作为潜在抗疟药的合成与构效关系。

  摘要：

  已鉴定出一系列二芳基醚取代的4-吡啶酮，其在体外和体内对鼠恶性疟原虫的有效抗疟活性优于氯喹对恶性疟原虫的抗疟活性。这些是通过对侧链变化对活性的影响进行系统研究而从抗球虫药clopidol衍生而来的。相对于氯吡咯醇，最具活性的化合物在体外抑制恶性疟原虫的IC50改善了500倍以上，而在小鼠中相对于针对约氏疟原虫的ED50则提高了约100倍。这些化合物已在其他地方显示出通过抑制细胞色素bc1络合物处线粒体电子传递的作用而选择性发挥作用。

  DOI：

  10.1021/jm0705760

文献信息

• Heterocyclic compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0447164A1

  公开（公告）日：1991-09-18

  A compound of formula (I):- wherein R¹ represents a hydrogen or halogen atom, or a cyano group; R² represents an optionally substituted carbocyclic group having 6 to 10 ring atoms and containing at least one aromatic ring; an optionally substituted heterocyclic group having 5 to 10 ring atoms, including 1 to 4 heteroatoms selected from O,N and S, and containing at least one aromatic ring; or an optionally substituted C₃₋₆cycloalkyl, C₃₋₆cycloalkyl- C₁₋₆alkyl, or C₁₋₁₀alkyl group; R³ and R⁴, which may be the same or different, each represent    a hydrogen or halogen atom, or a C₁₋₆alkyl group optionally substituted by 1 to 3 halogen atoms; and R⁵ represents    a hydrogen atom, a hydroxyl group, or a C₁₋₆alkyl group, optionally substituted by hydroxy, carboxy, amino or mono- or di-(C₁₋₄)alkyl amino,    and salts and other physiologically functional derivative thereof. The compounds are useful in the treatment of parasitic infections eg. malaria, coccidiosis and Pneumocystis carinii pneumonia.

  化合物的化学式为（I）：其中R¹代表氢原子或卤素原子或氰基；R²代表可选取代的碳环基团，其有6至10个环原子并含有至少一个芳香环；可选取代的杂环基团，其有5至10个环原子，包括1至4个从O、N和S中选取的杂原子，并含有至少一个芳香环；或可选取代的C₃₋₆环烷基、C₃₋₆环烷基- C₁₋₆烷基，或C₁₋₁₀烷基；R³和R⁴，它们可以相同也可以不同，每个代表氢原子或卤素原子，或由1至3个卤素原子取代的C₁₋₆烷基；R⁵代表氢原子、羟基，或由羟基、羧基、氨基或单烷基或双烷基(C₁₋₄)氨基取代的C₁₋₆烷基，以及其盐和其他生理功能衍生物。这些化合物在治疗寄生虫感染，例如疟疾、球虫病和肺孢子虫肺炎中有用。
• Pyridine derivatives
  申请人：ZENECA LIMITED

  公开号：EP0453210A2

  公开（公告）日：1991-10-23

  The invention concerns pharmaceutically useful novel compounds of the formula I, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.

  本发明涉及在医药上有用的式 I 新型化合物及其无毒盐，以及含有它们的药物组合物。这些新型化合物具有治疗高血压和充血性心力衰竭等疾病的价值。本发明还涉及新型化合物的生产工艺以及这些化合物在医疗中的用途。
• New nonpeptide angiotensin II receptor antagonists. 3. Synthesis, biological properties, and structure-activity relationships of 2-alkyl-4-(biphenylylmethoxy)pyridine derivatives
  作者：Robert H. Bradbury、Christopher P. Allott、Michael Dennis、J. Alan Girdwood、Peter W. Kenny、John S. Major、Alec A. Oldham、Arnold H. Ratcliffe、Janet E. Rivett

  DOI：10.1021/jm00061a016

  日期：1993.4

  A novel series of nonpeptide angiotensin II (AII) receptor antagonists is reported, derived from linkage of the biphenylyltetrazole moiety found in previously described antagonists via a methyleneoxy chain to the 4-position of a 3-substituted 2,6-dialkylpyridine. When evaluated in an in vitro binding assay using a guinea pig adrenal membrane preparation, compounds in this series generally gave IC50 values in the range 0.005-0.5 muM. A variety of substituents was found to be effective at the 3-position of the pyridine ring. On intravenous administration in a normotensive rat model, the more potent compounds inhibited the AII-induced pressor response with ED50 values in the range 0.1-1.0 mg/kg. One of the compounds, 2-ethyl-5,6,7,8-tetrahydro-4-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methoxy}quinoline (26), demonstrated good oral activity in two rat models. At doses in the range 1-10 mg/kg po in AII-infused, conscious, normotensive rats, the compound exhibited a dose-related inhibition of the pressor response with a good duration of action at the higher doses. In a renal hypertensive rat model compound 26 showed a rapid and sustained lowering of blood pressure at a dose of 5 mg/kg po. Based on its profile, this compound, designated ICI D6888, has been selected for evaluation in volunteers.
• US5130318A
  申请人：——

  公开号：US5130318A

  公开（公告）日：1992-07-14
• US5198439A
  申请人：——

  公开号：US5198439A

  公开（公告）日：1993-03-30

表征谱图