flavanthridin | 130827-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: flavanthridin
• 英文别名: 3,7-dihydroxy-2,4-dimethoxy-9,10-dihydrophenanthrene；ephemeranthol B；5,7-dimethoxy-9,10-dihydrophenanthrene-2,6-diol
• CAS: 130827-44-0
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: SOHTUOALNFQEMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  flavanthridin 、 乙酸酐 在 吡啶 作用下， 生成 flavanthridin diacetate
  参考文献：
  名称：

  来自兰花 Eria flava 的两种芪类

  摘要：

  摘要 Flavanthridin 和 flavanthrinin 这两种新的芪类化合物是从兰花 Eria flava 中分离出来的，它们还提供了 2,7-dihydroxy-4-methoxy-9,10-dihydrophenanthrene (coelonin)、它的 1,1'-二聚体 (flavanthrin) 和 3 ,7-二羟基-2,4-二甲氧基菲的先前已知结构。黄芪和黄芪的结构分别为3,7-二羟基-2,4-二甲氧基-9,10-二氢菲和2,7-二羟基-4-甲氧基菲。

  DOI：

  10.1016/0031-9422(90)87141-g
• 作为产物：
  描述：

  3,7-dihydroxy-2,4-dimethoxyphenanthrene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 flavanthridin
  参考文献：
  名称：

  Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential

  摘要：

  Regioselective synthesis of 9,10-Dihydro-2,5-Dimethoxyphenanthrene-1,7-diol (1) and 9,10-Dihydro-2,7-Dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.016

文献信息

• MAJUMDER, P. L.;BANERJEE, S., PHYTOCHEMISTRY, 29,(1990) N, C. 3052-3055
  作者：MAJUMDER, P. L.、BANERJEE, S.

  DOI：——

  日期：——
• Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential
  作者：Yogesh Kanekar、Khalander Basha、Sharad Duche、Rajan Gupte、Arnab Kapat

  DOI：10.1016/j.ejmech.2013.06.016

  日期：2013.9

  Regioselective synthesis of 9,10-Dihydro-2,5-Dimethoxyphenanthrene-1,7-diol (1) and 9,10-Dihydro-2,7-Dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Two stilbenoids from the orchid Eria flava
  作者：P.L. Majumder、S. Banerjee (Née Bhattacharyya)

  DOI：10.1016/0031-9422(90)87141-g

  日期：1990.1

  Abstract Flavanthridin and flavanthrinin, two new stilbenoids, were isolated from the orchid Eria flava which also afforded 2,7-dihydroxy-4-methoxy-9,10-dihydrophenanthrene (coelonin), its 1,1′-dimer (flavanthrin) and 3,7-dihydroxy-2,4-dimethoxyphenanthrene of previously known structures. The structures of flavanthridin and flavanthrinin were established as 3,7-dihydroxy-2,4-dimethoxy-9,10-dihydrophenanthrene

  摘要 Flavanthridin 和 flavanthrinin 这两种新的芪类化合物是从兰花 Eria flava 中分离出来的，它们还提供了 2,7-dihydroxy-4-methoxy-9,10-dihydrophenanthrene (coelonin)、它的 1,1'-二聚体 (flavanthrin) 和 3 ,7-二羟基-2,4-二甲氧基菲的先前已知结构。黄芪和黄芪的结构分别为3,7-二羟基-2,4-二甲氧基-9,10-二氢菲和2,7-二羟基-4-甲氧基菲。