9-Diethylamino-2-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-benzo[a]phenoxazin-5-one | 888327-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 9-Diethylamino-2-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-benzo[a]phenoxazin-5-one
• 英文别名: 9-(diethylamino)-2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]benzo[a]phenoxazin-5-one
• CAS: 888327-70-6
• 化学式: C₂₅H₂₆N₂O₅
• 分子量: 434.492
• InChiKey: LGHRUDBPPFJMRU-YZUZCNPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-Diethylamino-2-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-benzo[a]phenoxazin-5-one 在 吡啶 、 四氮唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(9-diethylamino-5-oxo-5H-benzo[a]phenoxazin-2-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Nile Red Nucleoside:  Design of a Solvatofluorochromic Nucleoside as an Indicator of Micropolarity around DNA

  摘要：

  The fluorophore, Nile Red, effectively works as a polarity-sensitive fluorescence probe. We have designed a new nucleoside modified by Nile Red for examining the change in the polarity of the microenvironment surrounding DNA. We synthesized a Nile Red nucleoside (1), formed by replacing nucleobases with Nile Red, through the coupling of a 2-hydroxylated Nile Red derivative and 1,2-dideoxyglycan. This nucleoside showed a high solvatofluorochromicity. The fluorescence of 1 incorporated into DNA was greatly shifted to shorter wavelength by the addition of beta-cyclodextrin. The photophysical function of the Nile Red nucleoside will be a good optical indicator for monitoring the change in the micropolarity properties at a specific site on target sequences with interaction between DNA and DNA-binding molecules.

  DOI：

  10.1021/jo060168o
• 作为产物：
  描述：

  9-(diethylamino)-5-hydroxybenzo[a]phenoxazin-2-one 在 palladium diacetate 4 A molecular sieve 、 四丁基氯化铵 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 9-Diethylamino-2-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-benzo[a]phenoxazin-5-one
  参考文献：
  名称：

  Nile Red Nucleoside:  Design of a Solvatofluorochromic Nucleoside as an Indicator of Micropolarity around DNA

  摘要：

  The fluorophore, Nile Red, effectively works as a polarity-sensitive fluorescence probe. We have designed a new nucleoside modified by Nile Red for examining the change in the polarity of the microenvironment surrounding DNA. We synthesized a Nile Red nucleoside (1), formed by replacing nucleobases with Nile Red, through the coupling of a 2-hydroxylated Nile Red derivative and 1,2-dideoxyglycan. This nucleoside showed a high solvatofluorochromicity. The fluorescence of 1 incorporated into DNA was greatly shifted to shorter wavelength by the addition of beta-cyclodextrin. The photophysical function of the Nile Red nucleoside will be a good optical indicator for monitoring the change in the micropolarity properties at a specific site on target sequences with interaction between DNA and DNA-binding molecules.

  DOI：

  10.1021/jo060168o

文献信息

• Nile Red Nucleoside:  Design of a Solvatofluorochromic Nucleoside as an Indicator of Micropolarity around DNA
  作者：Akimitsu Okamoto、Kazuki Tainaka、Yoshimasa Fujiwara

  DOI：10.1021/jo060168o

  日期：2006.4.1

  The fluorophore, Nile Red, effectively works as a polarity-sensitive fluorescence probe. We have designed a new nucleoside modified by Nile Red for examining the change in the polarity of the microenvironment surrounding DNA. We synthesized a Nile Red nucleoside (1), formed by replacing nucleobases with Nile Red, through the coupling of a 2-hydroxylated Nile Red derivative and 1,2-dideoxyglycan. This nucleoside showed a high solvatofluorochromicity. The fluorescence of 1 incorporated into DNA was greatly shifted to shorter wavelength by the addition of beta-cyclodextrin. The photophysical function of the Nile Red nucleoside will be a good optical indicator for monitoring the change in the micropolarity properties at a specific site on target sequences with interaction between DNA and DNA-binding molecules.