3-methylene-2-(4-pyridyl)flavanone | 77038-46-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-methylene-2-(4-pyridyl)flavanone
• 英文别名: 3-Methylidene-2-phenyl-2-pyridin-4-ylchromen-4-one
• CAS: 77038-46-1
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: WJLKIGRXPQUBMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四甲基甲烷二胺 、 2-(4-pyridyl)flavanone 在 乙酸酐 作用下， 反应 1.0h， 以55%的产率得到3-methylene-2-(4-pyridyl)flavanone
  参考文献：
  名称：

  Antimicrobial 3-methylene flavanones

  摘要：

  The antimicrobial activity previously attributed to flavanone Mannich bases was found to be due to their breakdown products, 3-methyleneflavanones. Among the latter compounds, highest potency was observed when the flavanone phenyl ring contained bromine or chlorine substituents. 3-Methylene-2-phenylflavanone (8) was synthesized and shown to be equal to hexachlorophene in tests against representative Gram-positive microorganisms.

  DOI：

  10.1021/jm00141a011

文献信息

• 3-Methylene flavanones and 3-methylene chromanones, antimicrobial composition containing same and method of inhibiting the growth of microorganisms
  申请人：MILES LABORATORIES, INC.

  公开号：EP0025161A1

  公开（公告）日：1981-03-18

  Compounds which are 3-methylene flavanones and 3-methylene chromanones having activity against microorganisms are disclosed. The compounds are represented by the general structural formula: wherein: R' is a member selected from the group consisting of hydrogen, Br, CH3 and OCH3; R2 is selected from the group consisting of hydrogen and wherein R4 is a member selected from the group consisting of hydrogen, Br, Cl, CH3, OCH3, NO2, N/CH3)2, C(CH3)3 and CN; R' is selected from the group consisting of hydrogen and Cl, with the proviso that when R5 is Cl, R' is hydrogen or Cl; and R3 is selected from the group consisting of hydrogen, phenyl, 2-thienyl, 4-pyridyl and naphthyl, with the proviso that when R3 is naphthyl, R1 and R2 are hydrogen.

  本发明公开了具有抗微生物活性的 3-亚甲基黄烷酮和 3-亚甲基色满酮化合物。这些化合物由一般结构式表示： 其中R'选自由氢、Br、CH3 和 OCH3 组成的组 其中 R4 选自由氢、Br、Cl、CH3、OCH3、NO2、N/CH3)2、C(CH3)3 和 CN 组成的组；R'选自由氢和 Cl 组成的组，但当 R5 为 Cl 时，R'为氢或 Cl；以及 R3 选自由氢、苯基、2-噻吩基、4-吡啶基和萘基组成的组，但当 R3 为萘基时，R1 和 R2 为氢。
• WARD, F. E.;GARLING, D. L.;BUCKLER, R. T.;LAWLER, D. M.;CUMMINGS, D. P., J. MED. CHEM., 1981, 24, N 9, 1073-1077
  作者：WARD, F. E.、GARLING, D. L.、BUCKLER, R. T.、LAWLER, D. M.、CUMMINGS, D. P.

  DOI：——

  日期：——
• US4241069A
  申请人：——

  公开号：US4241069A

  公开（公告）日：1980-12-23
• Antimicrobial 3-methylene flavanones
  作者：Frederick E. Ward、David L. Garling、Robert T. Buckler、David M. Lawler、Dennis P. Cummings

  DOI：10.1021/jm00141a011

  日期：1981.9

  The antimicrobial activity previously attributed to flavanone Mannich bases was found to be due to their breakdown products, 3-methyleneflavanones. Among the latter compounds, highest potency was observed when the flavanone phenyl ring contained bromine or chlorine substituents. 3-Methylene-2-phenylflavanone (8) was synthesized and shown to be equal to hexachlorophene in tests against representative Gram-positive microorganisms.