glutaric acid mono-(α,α-dideuterio-4,5-dimethoxy-2-nitrobenzyl) ester | 724763-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: glutaric acid mono-(α,α-dideuterio-4,5-dimethoxy-2-nitrobenzyl) ester
• 英文别名: 5-[Dideuterio-(4,5-dimethoxy-2-nitrophenyl)methoxy]-5-oxopentanoic acid；5-[dideuterio-(4,5-dimethoxy-2-nitrophenyl)methoxy]-5-oxopentanoic acid
• CAS: 724763-09-1
• 化学式: C₁₄H₁₇NO₈
• 分子量: 329.275
• InChiKey: MSPFMZDKLXGBMN-MGVXTIMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  glutaric acid mono-(α,α-dideuterio-4,5-dimethoxy-2-nitrobenzyl) ester 、 4-phenyl-2-nitrobenzyl alcohol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以93%的产率得到glutaric acid (α,α-dideuterio-4,5-dimethoxy-2-nitrobenzyl) ester (4-phenyl-2-nitrobenzyl) ester
  参考文献：
  名称：

  Isotope Effects in Photochemistry:  Application to Chromatic Orthogonality

  摘要：

  The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled by two factors: the chromophore absorbance and the reaction quantum yield. Fine-tuning the properties by changing substituents or structural features is difficult, because both factors are independently affected. By the use of the kinetic isotope effect, we could tune the quantum yield without altering the absorbance, and hence control the overall reaction rate. We exemplified this approach with chromatically orthogonally protected diesters.

  DOI：

  10.1021/ol070820h
• 作为产物：
  描述：

  戊二酸酐 、 4,5-dimethoxy-2-nitrobenzyl-α,α-d2 alcohol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以46%的产率得到glutaric acid mono-(α,α-dideuterio-4,5-dimethoxy-2-nitrobenzyl) ester
  参考文献：
  名称：

  Isotope Effects in Photochemistry:  Application to Chromatic Orthogonality

  摘要：

  The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled by two factors: the chromophore absorbance and the reaction quantum yield. Fine-tuning the properties by changing substituents or structural features is difficult, because both factors are independently affected. By the use of the kinetic isotope effect, we could tune the quantum yield without altering the absorbance, and hence control the overall reaction rate. We exemplified this approach with chromatically orthogonally protected diesters.

  DOI：

  10.1021/ol070820h

文献信息

• Isotope Effects in Photochemistry:  Application to Chromatic Orthogonality
  作者：Aurélien Blanc、Christian G. Bochet

  DOI：10.1021/ol070820h

  日期：2007.7.1

  The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled by two factors: the chromophore absorbance and the reaction quantum yield. Fine-tuning the properties by changing substituents or structural features is difficult, because both factors are independently affected. By the use of the kinetic isotope effect, we could tune the quantum yield without altering the absorbance, and hence control the overall reaction rate. We exemplified this approach with chromatically orthogonally protected diesters.