(6-bromo-7-(2-oxo-2-(prop-2-yn-1-ylamino)ethoxy)coumarin-4-yl)methyl diethylphosphate | 1414975-56-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (6-bromo-7-(2-oxo-2-(prop-2-yn-1-ylamino)ethoxy)coumarin-4-yl)methyl diethylphosphate
• 英文别名: 2-[6-bromo-4-[[diethoxy(oxido)phosphaniumyl]oxymethyl]-2-oxochromen-7-yl]oxy-N-prop-2-ynylacetamide
• CAS: 1414975-56-6
• 化学式: C₁₉H₂₁BrNO₈P
• 分子量: 502.255
• InChiKey: FOONNQKJOQBGAE-UHFFFAOYSA-N

物化性质

• 沸点：
  664.3±55.0 °C(predicted)
• 密度：
  1.471±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (6-bromo-7-(2-oxo-2-(prop-2-yn-1-ylamino)ethoxy)coumarin-4-yl)methyl diethylphosphate 在 MOPS-K 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Design, Synthesis, and Photochemistry of Modular Caging Groups for Photoreleasable Nucleotides

  摘要：

  A modular approach to preparing caged nucleotides having additional properties has been achieved. The modular caging agent includes three components: an amine reactive NHS ester moiety, a photoactive Bhc group, and tosylhydrazone as a precursor of the diazomethyl group. Various amines including biotin and an Arg-Gly-Asp (RGD) peptide were introduced into the key intermediate via amide linkage. The Bio-Bhc-diazo thus synthesized enables the preparation of a photoreleasable siRNA with additional properties.

  DOI：

  10.1021/ol3029093
• 作为产物：
  描述：

  6-溴-7-羟基-4-(羟甲基)香豆素 在 三乙胺 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 219.5h， 生成 (6-bromo-7-(2-oxo-2-(prop-2-yn-1-ylamino)ethoxy)coumarin-4-yl)methyl diethylphosphate
  参考文献：
  名称：

  Design, Synthesis, and Photochemistry of Modular Caging Groups for Photoreleasable Nucleotides

  摘要：

  A modular approach to preparing caged nucleotides having additional properties has been achieved. The modular caging agent includes three components: an amine reactive NHS ester moiety, a photoactive Bhc group, and tosylhydrazone as a precursor of the diazomethyl group. Various amines including biotin and an Arg-Gly-Asp (RGD) peptide were introduced into the key intermediate via amide linkage. The Bio-Bhc-diazo thus synthesized enables the preparation of a photoreleasable siRNA with additional properties.

  DOI：

  10.1021/ol3029093

文献信息

• Design, Synthesis, and Photochemistry of Modular Caging Groups for Photoreleasable Nucleotides
  作者：Toshiaki Furuta、Kaori Manabe、Aoi Teraoka、Kanako Murakoshi、Ai Ohtsubo、Akinobu Suzuki

  DOI：10.1021/ol3029093

  日期：2012.12.21

  A modular approach to preparing caged nucleotides having additional properties has been achieved. The modular caging agent includes three components: an amine reactive NHS ester moiety, a photoactive Bhc group, and tosylhydrazone as a precursor of the diazomethyl group. Various amines including biotin and an Arg-Gly-Asp (RGD) peptide were introduced into the key intermediate via amide linkage. The Bio-Bhc-diazo thus synthesized enables the preparation of a photoreleasable siRNA with additional properties.