3'-[[3-[3-[2-(9-Tert-butyl-17-methoxy-13-oxa-3,4,5-triazatetracyclo[13.4.0.02,6.07,12]nonadeca-1(15),2(6),4,7(12),8,10,16,18-octaen-3-yl)ethoxy]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methoxy]-6'-[(3-hydroxynaphthalen-2-yl)methoxy]spiro[2-benzofuran-3,9'-xanthene]-1-one | 1621132-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3'-[[3-[3-[2-(9-Tert-butyl-17-methoxy-13-oxa-3,4,5-triazatetracyclo[13.4.0.02,6.07,12]nonadeca-1(15),2(6),4,7(12),8,10,16,18-octaen-3-yl)ethoxy]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methoxy]-6'-[(3-hydroxynaphthalen-2-yl)methoxy]spiro[2-benzofuran-3,9'-xanthene]-1-one
• 英文别名: 3'-[[3-[3-[2-(9-tert-butyl-17-methoxy-13-oxa-3,4,5-triazatetracyclo[13.4.0.02,6.07,12]nonadeca-1(15),2(6),4,7(12),8,10,16,18-octaen-3-yl)ethoxy]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methoxy]-6'-[(3-hydroxynaphthalen-2-yl)methoxy]spiro[2-benzofuran-3,9'-xanthene]-1-one
• CAS: 1621132-92-0
• 化学式: C₆₃H₅₂N₄O₁₀
• 分子量: 1025.13
• InChiKey: MQEPQZUSUMFFEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  77
• 可旋转键数：
  13
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  荧光素 在 caesium carbonate 、 三乙胺 、 sodium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 17.0h， 生成 3'-[[3-[3-[2-(9-Tert-butyl-17-methoxy-13-oxa-3,4,5-triazatetracyclo[13.4.0.02,6.07,12]nonadeca-1(15),2(6),4,7(12),8,10,16,18-octaen-3-yl)ethoxy]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methoxy]-6'-[(3-hydroxynaphthalen-2-yl)methoxy]spiro[2-benzofuran-3,9'-xanthene]-1-one
  参考文献：
  名称：

  Photoactivatable Fluorescein Derivatives Caged with a (3-Hydroxy-2-naphthalenyl)methyl Group

  摘要：

  The (3-hydroxy-2-naphthalenyl)methyl (NQMP) group represents an efficient photocage for fluorescein-based dyes. Thus, irradiation of the 6-NQMP ether of 2'-hydroxymethylfluorescein with low-intensity UVA light results in a 4-fold increase in emission intensity. Photoactivation of nonfluorescent NQMP-caged 3-allyloxyfluorescein produces a highly emissive fluorescein monoether. To facilitate conjugation of the caged dye to the substrate of interest via click chemistry, the allyloxy appendage was functionalized with an azide moiety.

  DOI：

  10.1021/jo501116g

文献信息

• Photoactivatable Fluorescein Derivatives Caged with a (3-Hydroxy-2-naphthalenyl)methyl Group
  作者：Emmanuel E. Nekongo、Vladimir V. Popik

  DOI：10.1021/jo501116g

  日期：2014.8.15

  The (3-hydroxy-2-naphthalenyl)methyl (NQMP) group represents an efficient photocage for fluorescein-based dyes. Thus, irradiation of the 6-NQMP ether of 2'-hydroxymethylfluorescein with low-intensity UVA light results in a 4-fold increase in emission intensity. Photoactivation of nonfluorescent NQMP-caged 3-allyloxyfluorescein produces a highly emissive fluorescein monoether. To facilitate conjugation of the caged dye to the substrate of interest via click chemistry, the allyloxy appendage was functionalized with an azide moiety.