7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-hydroxy-4H-chromen-4-one | 172805-73-1

• 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: 7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-hydroxy-4H-chromen-4-one
• 英文别名: 7,3'-O-dibenzyldiosmetin；7,3'-dibenzyldiosmetin；5-Hydroxy-2-(4-methoxy-3-phenylmethoxyphenyl)-7-phenylmethoxychromen-4-one；5-hydroxy-2-(4-methoxy-3-phenylmethoxyphenyl)-7-phenylmethoxychromen-4-one
• CAS: 172805-73-1
• 化学式: C₃₀H₂₄O₆
• 分子量: 480.517
• InChiKey: BKKYVCKTKBWRHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-hydroxy-4H-chromen-4-one 在 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 calcium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以77%的产率得到7,3'-dibenzyl-6-iododiosmetin
  参考文献：
  名称：

  二氯碘酸苄基三甲基铵对5,7-二加氧黄酮的区域选择性6-碘化

  摘要：

  本说明介绍了在室温下，在系统CH 2 Cl 2 -MeOH-CaCO 3中用1当量的苄基三甲基二氯碘酸铵（BTMA·ICl 2）对5,7-双加氧黄酮进行碘化。在C5处具有游离酚基的黄酮和在C7处具有烷氧基或过酰基糖基糖氧基的黄酮导致具有良好区域选择性的6-碘黄酮（6-碘化/ 8-碘化比约为9）。

  DOI：

  10.1016/j.tetlet.2004.03.038
• 作为产物：
  描述：

  香叶木素 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以60%的产率得到7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  A convenient microwave-assisted 5-amination of flavones

  摘要：

  A few examples of 5-aminoflavones' syntheses exist in the literature and for those, which are described, the amino group is introduced before the formation of the flavone skeleton. We describe here an efficient method, which permits the access to 5-aminoflavones by a simple procedure Using all SNAr amination under microwaves irradiation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.043

文献信息

• Semisynthesis of Linarin, Acacetin, and 6-Iodoapigenin Derivatives from Diosmin
  作者：Jérôme Quintin、Guy Lewin

  DOI：10.1021/np040079b

  日期：2004.9.1

  Semisynthesis of linarin and acacetin from the Citrus flavonoid diosmin was performed via, as first intermediate, the 3'-O-phenyltetrazolyl ether of diosmin. This paper relates also a semisynthetic access to 6-iodoapigenin derivatives, which are key compounds in the synthesis of some biflavonoids such as robustaflavone.
• Mosquera; Orjales, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 1, p. 19 - 22
  作者：Mosquera、Orjales

  DOI：——

  日期：——
• Flavonoid-Related Modulators of Multidrug Resistance:  Synthesis, Pharmacological Activity, and Structure−Activity Relationships
  作者：Jacques Ferté、Jean-Marc Kühnel、Geneviève Chapuis、Yves Rolland、Guy Lewin、Marc A. Schwaller

  DOI：10.1021/jm981064b

  日期：1999.2.1

  A series of 28 flavonoid derivatives containing a N-benzylpiperazine chain have been synthesized and tested for their ability to modulate multidrug resistance (MDR) in vitro. At 5 mu M, most compounds potentiated doxorubicin cytotoxicity on resistant K562/DOX cells. They were also able to increase the intracellular accumulation of JC-1, a fluorescent molecule recently described as a probe of P-glycoprotein-mediated MDR. This suggests that these compounds act, at least in part, by inhibiting P-glycoprotein activity. As in other studies, lipophilicity was shown to influence MDR-modulating activity but was not the only determinant. Diverse di- and trimethoxy substitutions on N-benzyl were examined and found to affect the activity differently. The most active compounds had a 2,3,4-trimethoxybenzylpiperazine chain attached to either a flavone or a flavanone moiety (13, 19, 33, and 37) and were found to be more potent; than verapamil.
• Regioselective 6-iodination of 5,7-dioxygenated flavones by benzyltrimethylammonium dichloroiodate
  作者：Jérôme Quintin、Guy Lewin

  DOI：10.1016/j.tetlet.2004.03.038

  日期：2004.4

  The iodination of 5,7-dioxygenated flavones with 1 equiv of benzyltrimethylammonium dichloroiodate (BTMA·ICl2) in the system CH2Cl2–MeOH–CaCO3 at room temperature is presented in this note. Flavones with a free phenol group at C5 and an alkoxy or a peracylglycosyloxy at C7 lead to the 6-iodoflavones with a good regioselectivity (ratio 6-iodination/8-iodination about 9).

  本说明介绍了在室温下，在系统CH 2 Cl 2 -MeOH-CaCO 3中用1当量的苄基三甲基二氯碘酸铵（BTMA·ICl 2）对5,7-双加氧黄酮进行碘化。在C5处具有游离酚基的黄酮和在C7处具有烷氧基或过酰基糖基糖氧基的黄酮导致具有良好区域选择性的6-碘黄酮（6-碘化/ 8-碘化比约为9）。
• A convenient microwave-assisted 5-amination of flavones
  作者：Cédric Lecoutey、Christine Fossey、Luc Demuynck、François Lefoulon、Frédéric Fabis、Sylvain Rault

  DOI：10.1016/j.tet.2008.09.043

  日期：2008.12

  A few examples of 5-aminoflavones' syntheses exist in the literature and for those, which are described, the amino group is introduced before the formation of the flavone skeleton. We describe here an efficient method, which permits the access to 5-aminoflavones by a simple procedure Using all SNAr amination under microwaves irradiation. (C) 2008 Elsevier Ltd. All rights reserved.