5-hydroxy-4'-methoxyflavone | 6665-72-1

• 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: 5-hydroxy-4'-methoxyflavone
• 英文别名: 4'-Methoxy-5-hydroxyflavone；5-hydroxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 6665-72-1
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: WAGFUKCEIMCKQR-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  456.0±45.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  5-hydroxy-4'-methoxyflavone 在 吡啶 、 氢氧化钾 、 dipotassium peroxodisulfate 作用下， 生成 5,8-diacetoxy-2-(4-methoxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  Baker et al., Journal of the Chemical Society, 1949, p. 1560

  摘要：

  DOI：
• 作为产物：
  描述：

  4,6'-dimethoxy-2'-hydroxychalcone 在 盐酸 、 三氯化铝 、 碘 作用下， 生成 5-hydroxy-4'-methoxyflavone
  参考文献：
  名称：

  Silva, Artur M. S.; Cavaleiro, Jose A. S.; Tarrago, Georges, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 97 - 104

  摘要：

  DOI：

文献信息

• Unified Approach to (Thio)chromenones via One-Pot Friedel–Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones
  作者：Hun Young Kim、Eunsun Song、Kyungsoo Oh

  DOI：10.1021/acs.orglett.6b03348

  日期：2017.1.20

  method to chromenones and thiochromenones has been developed using a one-pot Friedel–Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability

  已经开发了一种简便的合成色农酮和硫代色农酮的方法，该方法使用炔烃与适当取代的苯甲酰氯的一锅法式Friedel-Crafts酰化反应。这种（硫代）色农酮的统一方法很容易适用于芳基和烷基炔烃，其中立体化学上定义明确的β-氯乙烯基酮中间体经历明显不同的环化途径。起始原料炔烃和苯甲酰氯的现成可用性以及实验的简便性使得当前合成（硫代）色农酮的方法快速，高效和实用。
• Process for preparation of polyhydric alcohols
  申请人：——

  公开号：US20020157939A1

  公开（公告）日：2002-10-31

  A process for preparing a polyhydric alcohol according to the invention comprises subjecting a polyhydric alcohol compound having protected hydroxy group(s) to microwave irradiation in the presence of basic compound(s) or acid(s) having an acid dissociation exponent (pKa) of −8 to 3 at 25° C. to remove the protecting groups of the hydroxy group of the polyhydric alcohol compound. The invention can provide an industrially advantageous process for preparing polyhydric alcohols by readily removing protecting group(s) from protected hydroxy group(s) of polyhydric alcohol compounds.

  根据该发明，制备多羟基醇的方法包括将具有受保护羟基的多羟基醇化合物置于存在具有25°C下酸解离指数（pKa）为-8至3的碱性化合物或酸性化合物的微波辐射中，以去除多羟基醇化合物的羟基的保护基。该发明可以通过轻松去除多羟基醇化合物中受保护羟基的保护基，提供一个工业上有利的制备多羟基醇的方法。
• A One-Step Synthesis of 5-Hydroxyflavones
  作者：Frédéric Bois、Chantal Beney、Anne-Marie Mariotte、Ahcène Boumendjel

  DOI：10.1055/s-1999-2844

  日期：1999.9

  5-hydroxy flavones were prepared in one step starting from 2,6-dihydroxyacetophenone. The latter was treated with an aroyl chloride in the presence of an excess of potassium carbonate to afford 5-hydroxyflavones.

  5- 羟基黄酮由 2,6-二羟基苯乙酮一步制备而成。后者在过量碳酸钾的存在下用酰氯处理，得到 5-羟基黄酮。
• Flavones from Callus Tissue of Iris ensata
  作者：E. V. Boltenkov、V. G. Rybin、E. V. Zarembo

  DOI：10.1007/s10600-005-0200-1

  日期：2005.9

  Flavonoids uncharacteristic of intact plants were isolated from callus tissue of Iris ensata and were identified as 5-hydroxy-4′-methoxyflavone, 5-hydroxy-3′-methoxyflavone, and 5-hydroxy-2′-methoxyflavone using PMR and mass spectrometry. It was proposed that the lack of growth of callus tissue after changing cultivation conditions was related to the inhibiting effect of these flavones on cell proliferation.

  从鸢尾花的愈伤组织中分离出完整植物中不常见的类黄酮，并使用PMR和质谱法鉴定为5-羟基-4′-甲氧基黄酮、5-羟基-3′-甲氧基黄酮和5-羟基-2′-甲氧基黄酮。有人提出，改变培养条件后愈伤组织缺乏生长与这些黄酮对细胞增殖的抑制作用有关。
• PROCESS FOR THE PREPARATION OF POLYHYDRIC ALCOHOLS
  申请人：National Institute of Advanced Industrial Science and Technology

  公开号：EP1298115A1

  公开（公告）日：2003-04-02

  A process for preparing a polyhydric alcohol according to the invention comprises subjecting a polyhydric alcohol compound having protected hydroxy group(s) to microwave irradiation in the presence of basic compound(s) or acid(s) having an acid dissociation exponent (pKa) of -8 to 3 at 25°C to remove the protecting groups of the hydroxy group of the polyhydric alcohol compound. The invention can provide an industrially advantageous process for preparing polyhydric alcohols by readily removing protecting group(s) from protected hydroxy group(s) of polyhydric alcohol compounds.

  根据本发明制备多元醇的工艺包括：在碱性化合物或酸解离指数（pKa）为-8 至 3 的酸存在下，在 25°C 的温度下，对具有受保护羟基的多元醇化合物进行微波辐照，以去除多元醇化合物羟基的保护基团。本发明可提供一种具有工业优势的制备多羟基醇的工艺，该工艺可轻松去除多羟基醇化合物受保护羟基上的保护基团。