2-[4-(6-Azidohexoxy)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one | 1072920-40-1

• 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: 2-[4-(6-Azidohexoxy)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• CAS: 1072920-40-1
• 化学式: C₂₁H₂₃N₃O₅
• 分子量: 397.431
• InChiKey: CLRXJSHTNAROET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  o-propargylfluorescein 、 2-[4-(6-Azidohexoxy)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one 在 copper(ll) sulfate pentahydrate 、 维生素 C 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以63%的产率得到3'-[[1-[6-[4-(5,7-Dihydroxy-4-oxo-2,3-dihydrochromen-2-yl)phenoxy]hexyl]triazol-4-yl]methoxy]-6'-hydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one
  参考文献：
  名称：

  Site-Specific Fluorescent Labeling Approaches for Naringenin, an Essential Flavonone in Plant Nitrogen-Fixation Signaling Pathways

  摘要：

  In search of an appropriate position for the fluorescent labeling. six chemically available positions of the flavonone core of naringenin have been examined. A number of azido-containing naringenin derivatives were accordingly prepared in various site-specific fashions. and the Mild CU(I)-catalyzed Huisgen 1-3-dipolar cycloaddition successfully served as the common "Click" labeling tool in the final steps. Oil the basis of the biological activities of the first batch of labeled compounds, further optimization at the C-6 position of naringenin finally afforded naringenin-flu (27). which acquired 20% of the potency of naringenin and presented good optical properties. Entry of naringenin-flu into living Rhizobium Cells was demonstrated by in vitro fluorescent imaging experiments.

  DOI：

  10.1021/jo8014165
• 作为产物：
  描述：

  2-[4-(6-Azidohexoxy)phenyl]-7-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-2,3-dihydrochromen-4-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到2-[4-(6-Azidohexoxy)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Site-Specific Fluorescent Labeling Approaches for Naringenin, an Essential Flavonone in Plant Nitrogen-Fixation Signaling Pathways

  摘要：

  In search of an appropriate position for the fluorescent labeling. six chemically available positions of the flavonone core of naringenin have been examined. A number of azido-containing naringenin derivatives were accordingly prepared in various site-specific fashions. and the Mild CU(I)-catalyzed Huisgen 1-3-dipolar cycloaddition successfully served as the common "Click" labeling tool in the final steps. Oil the basis of the biological activities of the first batch of labeled compounds, further optimization at the C-6 position of naringenin finally afforded naringenin-flu (27). which acquired 20% of the potency of naringenin and presented good optical properties. Entry of naringenin-flu into living Rhizobium Cells was demonstrated by in vitro fluorescent imaging experiments.

  DOI：

  10.1021/jo8014165

文献信息

• Site-Specific Fluorescent Labeling Approaches for Naringenin, an Essential Flavonone in Plant Nitrogen-Fixation Signaling Pathways
  作者：Lei Chen、Feng-Qing Li、Bi-He Hou、Guo-Fan Hong、Zhu-Jun Yao

  DOI：10.1021/jo8014165

  日期：2008.11.7

  In search of an appropriate position for the fluorescent labeling. six chemically available positions of the flavonone core of naringenin have been examined. A number of azido-containing naringenin derivatives were accordingly prepared in various site-specific fashions. and the Mild CU(I)-catalyzed Huisgen 1-3-dipolar cycloaddition successfully served as the common "Click" labeling tool in the final steps. Oil the basis of the biological activities of the first batch of labeled compounds, further optimization at the C-6 position of naringenin finally afforded naringenin-flu (27). which acquired 20% of the potency of naringenin and presented good optical properties. Entry of naringenin-flu into living Rhizobium Cells was demonstrated by in vitro fluorescent imaging experiments.