6-chloro-2-hydroxy-4-methylacetophenone | 24490-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-chloro-2-hydroxy-4-methylacetophenone
• 英文别名: 1-(2-Chloro-6-hydroxy-4-methylphenyl)ethanone
• CAS: 24490-25-3
• 化学式: C₉H₉ClO₂
• 分子量: 184.622
• InChiKey: RNPRNDPIGSQCEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,5-三甲氧基苯甲醛 、 6-chloro-2-hydroxy-4-methylacetophenone 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2′,4′,5′-trimethoxyflavonol derivatives as anti-inflammatory and antimicrobial agents

  摘要：

  A series of novel 3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (flavonol) derivatives (2a-u) of biological interest have been prepared via CLAISEN-SCHMIDT condensation followed by ALGAR-FLYNN-OYAMADA reaction and to search for the potent nonsteroidal anti-inflammatory agents from this novel series. All the synthesized compounds have been screened for their in vitro proinflammatory cytokines tumor necrosis factor (TNF-alpha) and interleukin-6 (IL-6) inhibitory activity along with antimicrobial activity. As many as three compounds viz. 2h, 2l, and 2q from this novel series were found to be potent TNF-alpha and IL-6 inhibitor (up to 72-81 % TNF-alpha and 86-92 % IL-6 inhibitory activity) but at 10 mu M concentration as compared with the standard dexamethasone (71 % TNF-alpha and 84 % IL-6 inhibitory activities at 1 mu M concentration). While the compounds 2d, 2m, 2n, and 2s were found to be potent antimicrobial agent showing even 2-2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL.

  DOI：

  10.1007/s00044-013-0651-z
• 作为产物：
  描述：

  (1S,6S)-7-Chloro-1,5-dimethyl-2-oxa-bicyclo[4.2.0]octa-4,7-dien-3-one 以 甲苯 为溶剂， 反应 80.0h， 生成 6-chloro-2-hydroxy-4-methylacetophenone
  参考文献：
  名称：

  RING-EXPANSION OF 7-CHLORO-2-OXABICYCLO[4.2.0]OCT-4-EN-3-ONES TO 2H-OXOCIN-2-ONES WITH BASE. FORMATION OF A NEW OXACYCLOOCTATRIENONE SYSTEM

  摘要：

  氯代 2-氧杂双环[4.2.0]辛-4-烯-3-酮是 4,6-二甲基-2-吡喃酮和氯代乙烯的光加成物，用碱处理可得到新的 2H-氧杂双环[4.2.0]辛-4-烯-3-酮，收率很高。这为制备单环氧杂环辛三烯酮体系提供了第一个实例。

  DOI：

  10.1246/cl.1984.1503

文献信息

• SHIMO, TETSURO;SOMEKAWA, KENICHI;KUWAKINO, JUNRO;UEMURA, HISAKO;KUMAMOTO,+, CHEM. LETT., 1984, N 9, 1503-1504
  作者：SHIMO, TETSURO、SOMEKAWA, KENICHI、KUWAKINO, JUNRO、UEMURA, HISAKO、KUMAMOTO,+

  DOI：——

  日期：——