3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone | 81325-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone
• 英文别名: 1-(3-chloro-2-hydroxy-4,6-dimethoxy-phenyl)-ethanone；1-(3-Chlor-2-hydroxy-4,6-dimethoxy-phenyl)-aethanon；1-(3-Chloro-2-hydroxy-4,6-dimethoxyphenyl)ethanone
• CAS: 81325-85-1
• 化学式: C₁₀H₁₁ClO₄
• 分子量: 230.648
• InChiKey: JXKHLCYYMOQYED-UHFFFAOYSA-N

物化性质

• 熔点：
  191–192°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone 在 盐酸 、 rhodium(II) pivalate 、 2,3-二巯基丁二酸 、 三丁基膦 、 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 sodium methylate 、 臭氧 、 三乙胺 、 甲烷磺酰基叠氮化物 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 3.0h， 生成 灰黄霉素
  参考文献：
  名称：

  Total synthesis of (+)-griseofulvin

  摘要：

  DOI：

  10.1021/ja00022a075
• 作为产物：
  描述：

  (2-chloro-3,5-dimethoxyphenyl) acetate 在 三氯化铝 作用下， 以 氯苯 为溶剂， 反应 0.5h， 以94%的产率得到3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone
  参考文献：
  名称：

  Total synthesis of (+)-griseofulvin

  摘要：

  DOI：

  10.1021/ja00022a075

文献信息

• 439. Griseofulvin. Part XVI. Synthesis of compounds related to griseofulvin
  作者：A. W. Dawkins、T. P. C. Mulholland

  DOI：10.1039/jr9590002203

  日期：——
• Duncanson et al., Journal of the Chemical Society, 1957, p. 3555,3557
  作者：Duncanson et al.

  DOI：——

  日期：——
• Synthesis of chlorinated flavonoids with anti-inflammatory and pro-apoptotic activities in human neutrophils
  作者：Marisa Freitas、Daniela Ribeiro、Sara M. Tomé、Artur M.S. Silva、Eduarda Fernandes

  DOI：10.1016/j.ejmech.2014.08.035

  日期：2014.10

  Neutrophils are considered the central cells of acute inflammation. Flavonoids have been suggested as therapeutic agents to avoid damages induced by inflammatory processes. It is well known the reactivity of flavonoids with hypochlorous acid produced by neutrophils, to form stable mono and dichlorinated products. In this study, we synthesized novel chlorinated flavonoids and investigated their effect in neutrophils' oxidative burst and in its lifespan, in comparison with the parent non-chlorinated flavonoids. The obtained results demonstrate that chlorinated flavonoids were more efficient than their parent compounds in modulating neutrophils' oxidative burst in phorbol myristate acetate-activated neutrophils. Some of the tested flavonoids drive neutrophil apoptosis in a caspase 3-dependent fashion. The present data showed that 8-chloro-3',4',5,7-tetrahydroxyflavone (4a) constitute an alternative anti-inflammatory therapy, due to the proven ability to suppress mechanisms engaged at the onset and progression of inflammation. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Nitration, amination, and halogenation of Di-O-methylphloracetophenone
  作者：John P. Acton、Dorothy J. Donnelly、John A. Donnelly

  DOI：10.1007/bf00814339

  日期：1982.1
• TOKES, ADRIENNE L., J. ANTIBIOTICS, 43,(1990) N0, C. 1332-1333
  作者：TOKES, ADRIENNE L.

  DOI：——

  日期：——