1-(3-乙酰基-2,4-二羟基-6-甲氧基苯基)-1-乙酮 | 3098-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-乙酰基-2,4-二羟基-6-甲氧基苯基)-1-乙酮
• 英文名称: 3'-acetyl-2',4'-dihydroxy-6'-methoxyacetophenone
• 英文别名: 1,3-diacetyl-2,4-dihydroxy-6-methoxybenzene；2,4-dihydroxy-6-methoxy-1,3-diacetylbenzene；2,4-diacetyl-5-methoxy-resorcinol；2,4-Diacetyl-5-methoxy-resorcin；1-(3-Acetyl-2,4-dihydroxy-6-methoxyphenyl)ethan-1-one；1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)ethanone
• CAS: 3098-38-2
• 化学式: C₁₁H₁₂O₅
• mdl: MFCD00100564
• 分子量: 224.213
• InChiKey: ZUQRDBCPZDOGMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  255-257 °C(Solv: methanol (67-56-1))
• 沸点：
  437.2±45.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-乙酰基-2,4-二羟基-6-甲氧基苯基)-1-乙酮 生成 2,8-Dicarboxy-4,10-dioxo-5-methoxy-4H,10H-benzo<1,2-b:3,4-b'>-dipyran
  参考文献：
  名称：

  CAIRNS, H.;MINSHULL, R.

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,2-三氯-1-(2,4-二羟基-6-甲氧基-苯基)-乙酮 在 三氟化硼 、 锌 作用下， 生成 1-(3-乙酰基-2,4-二羟基-6-甲氧基苯基)-1-乙酮
  参考文献：
  名称：

  713.有机氟化合物。第六部分 一些三氟甲基色酮和-香豆素

  摘要：

  DOI：

  10.1039/jr9510003235

文献信息

• Synthesis and structure revision of litseaone A
  作者：Hideaki Kageji、Naoki Mori、Hirosato Takikawa、Hidenori Watanabe

  DOI：10.1016/j.tet.2018.10.041

  日期：2018.12

  pedunculata, is a chalcone derivative with a novel spiro-epoxide moiety. The structural revision of litseaone A was achieved by the racemic synthesis of the proposed structure and the asymmetric synthesis of the revised structure. The major tautomeric structure of litseaone A and the relative stereochemistry at the epoxide carbon center were also clarified.

  Litseaone A，从茎皮中分离木姜子冬凌草和木姜子长柄，是具有新型螺-环氧化物部分的查耳酮衍生物。利西酮A的结构修饰是通过拟议结构的外消旋合成和修饰结构的不对称合成实现的。还阐明了litseaone A的主要互变异构结构和在环氧碳中心的相对立体化学。
• 249. Usnic acid. Part VIII. C-diacetyl derivatives of phloroglucinol and C-methylphloroglucinol
  作者：F. M. Dean、Alexander Robertson

  DOI：10.1039/jr9530001241

  日期：——
• Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect
  作者：Susanne Vogel、Matej Barbic、Guido Jürgenliemk、Jörg Heilmann

  DOI：10.1016/j.ejmech.2010.01.060

  日期：2010.6

  Besides 2',4'-dihydroxy-4,6'-dimethoxy-3'-prenylchalcone (1) and 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalkon (2), both phase II metabolites of xanthohumol in rats, also a principally new chalcone 3'-coumaroyl-2',4,4'-trihydroxy-6'-methoxychalcone (3), structurally derived from helichrysetin (4) by introducing a second coumaroyl substructure at C-3' was synthesized. Furthermore new chalcones were synthesized by combination of the B-Ring fragments of helichrysetin, xanthohumol, xanthohumol C and xanthohumol H with ferulic or caffeic acid moieties in Ring A. Compound 3 showed the highest cytotoxic activity against HeLa cells with an IC50 value of 7.3 +/- 04 mu M. Anti-oxidative effects were determined in the ORAC assay and revealed very strong activity for 3 and 3-methoxyhelichrysetin (6) exhibiting 7.7 +/- 0.3 and 6.0 +/- 1.3 Trolox equivalents, respectively. The anti-inflammatory activity of all compounds was measured in an in vitro ICAM-1 assay with human microvascular endothelial cells (HMEC-1) and compared with the activity of other structurally related chalcones. The results showed increasing anti-inflammatory activity for the new synthetic chalcones exhibiting a caffeoyl substructure with 3-hydroxyhelichrysetin (5) and 3-hydroxyxanthohumol H (14) being the most active. At 10 mu M the TNF alpha induced expression of ICAM-1 was significantly reduced to 65.8 and 69.6% of control, respectively.
• [EN] ANTI-VIRAL COMPOSITIONS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1991009595A1

  公开（公告）日：1991-07-11

  (EN) Phloroglucinol and derivatives of phloroglucinol are useful in treating immune dysfunction associated with infection by an Immunodeficiency Virus.(FR) Le phloroglucinol et les dérivés de phloroglucinol sont utiles dans le traitement des dysfonctionnements immunitaires associés à l'infection par un virus d'immunodéficience.