Scutellaprostin F | 137231-88-0

• 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: Scutellaprostin F
• 英文别名: (2R,3R)-7-(3,4-dihydroxyphenyl)-10-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydropyrano[2,3-g][1,4]benzodioxin-9-one
• CAS: 137231-88-0
• 化学式: C₂₅H₂₀O₁₀
• 分子量: 480.428
• InChiKey: LAVFGLAMSWJYME-ZJSXRUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Scutellaprostin F 在 吡啶 作用下， 生成 Scutellaprostin F pentaacetate
  参考文献：
  名称：

  Studies on Nepalese Crude Drugs. XIV. New Flavonoids from the Root of Scutellaria prostrata Jacq. ex Benth.

  摘要：

  从黄芩（唇形科植物）的根中分离出六种黄酮类化合物，分别命名为黄芩前列素 A、B、C、D、E 和 F。它们的结构被确定为：(2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-phenyl-2, 3-dihydro-7H-1, 4-dioxino[2, 3-h]chromene-7-one (I), (2R*, 3*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(4-hydroxyphenyl)-2、(2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]-chromene-7-one (II), (2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]chromene-7-one (III), (2R*、3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-phenyl-2, 3-dihydro-6H-1, 4-dioxino-[2, 3-g]chromene-6-one (IV), (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-(4-hydroxyphenyl)-2, 3-dihydro-6H-1,它们是在氧化银存在下通过黄酮和针叶醇的氧化偶联合成的。

  DOI：

  10.1248/cpb.39.1466
• 作为产物：
  描述：

  松柏醇 、 6-羟基四羟黄酮 在 silver(l) oxide 作用下， 以 丙酮 、 苯 为溶剂， 以650 mg的产率得到Scutellaprostin F
  参考文献：
  名称：

  Studies on Nepalese Crude Drugs. XIV. New Flavonoids from the Root of Scutellaria prostrata Jacq. ex Benth.

  摘要：

  从黄芩（唇形科植物）的根中分离出六种黄酮类化合物，分别命名为黄芩前列素 A、B、C、D、E 和 F。它们的结构被确定为：(2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-phenyl-2, 3-dihydro-7H-1, 4-dioxino[2, 3-h]chromene-7-one (I), (2R*, 3*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(4-hydroxyphenyl)-2、(2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]-chromene-7-one (II), (2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]chromene-7-one (III), (2R*、3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-phenyl-2, 3-dihydro-6H-1, 4-dioxino-[2, 3-g]chromene-6-one (IV), (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-(4-hydroxyphenyl)-2, 3-dihydro-6H-1,它们是在氧化银存在下通过黄酮和针叶醇的氧化偶联合成的。

  DOI：

  10.1248/cpb.39.1466

文献信息

• Studies on Nepalese Crude Drugs. XIV. New Flavonoids from the Root of Scutellaria prostrata Jacq. ex Benth.
  作者：Yuichi KIKUCHI、Yukinori MIYAICHI、Tsuyoshi TOMIMORI

  DOI：10.1248/cpb.39.1466

  日期：——

  Six flavonoids, named scutellaprostins A, B, C, D, E and F, were isolated from teh root of Scutellaria prostrata JACQ. ex BENTH. (Labiatae). Their structures were established to be (2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-phenyl-2, 3-dihydro-7H-1, 4-dioxino[2, 3-h]chromene-7-one (I), (2R*, 3*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(4-hydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino[2, 3-h]-chromene-7-one (II), (2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]chromene-7-one (III), (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-phenyl-2, 3-dihydro-6H-1, 4-dioxino-[2, 3-g]chromene-6-one (IV), (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-(4-hydroxyphenyl)-2, 3-dihydro-6H-1, 4-dioxino[2, 3-g]chromene-6-one (V) and (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-(3, 4-dihydroxyphenyl)-2, 3-dihydro-6H-1, 4-dioxino[2, 3-g]chromene-6-one (VI), respectively, by chemical and spectral data. They were synthesized by oxidative coupling of the flavones and coniferyl alcohol in the presence of silver oxide.

  从黄芩（唇形科植物）的根中分离出六种黄酮类化合物，分别命名为黄芩前列素 A、B、C、D、E 和 F。它们的结构被确定为：(2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-phenyl-2, 3-dihydro-7H-1, 4-dioxino[2, 3-h]chromene-7-one (I), (2R*, 3*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(4-hydroxyphenyl)-2、(2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]-chromene-7-one (II), (2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]chromene-7-one (III), (2R*、3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-phenyl-2, 3-dihydro-6H-1, 4-dioxino-[2, 3-g]chromene-6-one (IV), (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-(4-hydroxyphenyl)-2, 3-dihydro-6H-1,它们是在氧化银存在下通过黄酮和针叶醇的氧化偶联合成的。