α,α-dideuterio-4-chloro-2-nitrobenzyl alcohol | 945920-67-2

• 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: α,α-dideuterio-4-chloro-2-nitrobenzyl alcohol
• 英文别名: 4-chloro-2-nitrobenzyl-α,α-d2 alcohol
• CAS: 945920-67-2
• 化学式: C₇H₆ClNO₃
• 分子量: 189.567
• InChiKey: OAHGNOHGHOTZQU-APZFVMQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  α,α-dideuterio-4-chloro-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 、 乙腈 为溶剂， 反应 73.0h， 生成 glutaric acid (4-chloro-2-nitrobenzyl-α,α-d2) methyl 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：

  4-氯-2-硝基苯甲酸 在 氯化亚砜 、 硼氘化钠 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 α,α-dideuterio-4-chloro-2-nitrobenzyl alcohol
  参考文献：
  名称：

  Isotope Effects in Photochemistry. 1. o-Nitrobenzyl Alcohol Derivatives

  摘要：

  The photolysis of o-nitrobenzyl alcohol derivatives shows a strong kinetic isotope effect (KIE up to 8.3) at the benzylic center. For some derivatives, the KIE is wavelength dependent, suggesting the involvement of higher excited states. In addition to the important mechanistic consequences, isotopic substitution is a convenient way to alter the quantum yield without changing the absorbance, as would the introduction of substituents. This paves the way for a subtle tuning of the reaction rates in photochemical reactions. We illustrated this feature in the sequential deprotection of a diester protected at both termini with photolabile groups.

  DOI：

  10.1021/ja049686b