2,4,6-trihydroxy-5-methoxyacetophenone | 16297-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-trihydroxy-5-methoxyacetophenone
• 英文别名: 2,4,6-trihydroxy-3-methoxyacetophenone；1-(2,4,6-Trihydroxy-3-methoxy-phenyl)-ethanon；2,4,6-Trihydroxy-3-methoxy-acetophenon；1-(2,4,6-trihydroxy-3-methoxy-phenyl)-ethanone；1-(2,4,6-Trihydroxy-3-methoxy-phenyl)-aethanon；1-(2,4,6-Trihydroxy-3-methoxyphenyl)ethan-1-one；1-(2,4,6-trihydroxy-3-methoxyphenyl)ethanone
• CAS: 16297-01-1
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: MELNSSDJRUAVLP-UHFFFAOYSA-N

物化性质

• 熔点：
  188°C
• 沸点：
  332.9±37.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4,6-trihydroxy-5-methoxyacetophenone 在 吡啶 、 碘 、 sodium acetate 、 三氯化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 高车前素
  参考文献：
  名称：

  Total Synthesis of Hispidulin and the Structural Basis for Its Inhibition of Proto-oncogene Kinase Pim-1

  摘要：

  A new method is applied to synthesize hispidulin, a natural flavone with a broad spectrum of biological activities. Hispidulin exhibits inhibitory activity against the oncogenic protein kinase Pim-1. Crystallographic analysis of Pim-1 bound to hispidulin reveals a binding mode distinct from that of quercetin, suggesting that the binding potency of flavonoids is determined by their hydrogen-bonding interactions with the hinge region of the kinase. Overall, this work may facilitate construction of a library of hispidulin-derived compounds for investigating the structure activity relationship of flavone-based Pim-1 inhibitors.

  DOI：

  10.1021/acs.jnatprod.5b00324
• 作为产物：
  描述：

  2,4,6-tris(O-methoxymethyl)benzaldehyde 在 盐酸 、 三氟化硼乙醚 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 2,4,6-trihydroxy-5-methoxyacetophenone
  参考文献：
  名称：

  Total Synthesis of Hispidulin and the Structural Basis for Its Inhibition of Proto-oncogene Kinase Pim-1

  摘要：

  A new method is applied to synthesize hispidulin, a natural flavone with a broad spectrum of biological activities. Hispidulin exhibits inhibitory activity against the oncogenic protein kinase Pim-1. Crystallographic analysis of Pim-1 bound to hispidulin reveals a binding mode distinct from that of quercetin, suggesting that the binding potency of flavonoids is determined by their hydrogen-bonding interactions with the hinge region of the kinase. Overall, this work may facilitate construction of a library of hispidulin-derived compounds for investigating the structure activity relationship of flavone-based Pim-1 inhibitors.

  DOI：

  10.1021/acs.jnatprod.5b00324

文献信息

• METHOD FOR PREPARING HISPIDULIN AND ITS DERIVATIVES
  申请人：TAIPEI MEDICAL UNIVERSITY

  公开号：US20190322637A1

  公开（公告）日：2019-10-24

  Provided is a method for preparing hispidulin or a derivative thereof. The method includes selective protection of trihydroxybenzaldehyde, followed by regioselective iodination, selective protection, Stille coupling, Baeyer-Villiger oxidation and basic hydrolysis to obtain a protected intermediate compound. Then, alkylation, Claisen-Schmidt condensation, cyclization and deprotection of the protected intermediate compound are performed to obtain hispidulin or the derivative thereof. The present disclosure provides an efficient method for total synthesis of hispidulin or the derivative thereof with concise reaction steps and high yield.

  提供了一种制备hispidulin或其衍生物的方法。该方法包括选择性保护三羟基苯甲醛，然后进行选择性碘化、选择性保护、Stille偶联、Baeyer-Villiger氧化和碱性水解，以获得一种受保护的中间化合物。然后，进行烷基化、Claisen-Schmidt缩合、环化和去保护受保护中间化合物，以获得hispidulin或其衍生物。本公开提供了一种高效的hispidulin或其衍生物的全合成方法，具有简洁的反应步骤和高产率。
• 290. The constitution of oroxylin-A. Part II. Attempted synthesis of oroxylin-A and the synthesis of wogonin
  作者：R. C. Shah、C. R. Mehta、T. S. Wheeler

  DOI：10.1039/jr9380001555

  日期：——
• Phadke et al., Indian Journal of Chemistry, 1967, vol. 5, p. 131,133
  作者：Phadke et al.

  DOI：——

  日期：——