N-Acetyl-3-nitro-L-tyrosin | 13948-21-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Acetyl-3-nitro-L-tyrosin
• 英文别名: 3-Nitro-N-acetyl-L-tyrosine；(2S)-2-acetamido-3-(4-hydroxy-3-nitrophenyl)propanoic acid
• CAS: 13948-21-5
• 化学式: C₁₁H₁₂N₂O₆
• 分子量: 268.226
• InChiKey: MYWCKMXQJXDPQZ-QMMMGPOBSA-N

物化性质

• 熔点：
  189-192 °C(Solv: water (7732-18-5))
• 沸点：
  569.8±50.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙醇 、 N-Acetyl-3-nitro-L-tyrosin 在 对甲苯磺酸 作用下， 生成 N-acetyl-L-3-nitrotyrosine ethyl ester
  参考文献：
  名称：

  518.甲状腺素和相关化合物的合成。第十五部分。由碘鎓盐和3,5-二取代酪氨酸衍生物制备甲状腺素

  摘要：

  DOI：

  10.1039/jr9610002645
• 作为产物：
  描述：

  N-乙酰-L-酪氨酸 在 Iron(III) nitrate nonahydrate 、 六氟异丙醇 作用下， 以81 %的产率得到N-Acetyl-3-nitro-L-tyrosin
  参考文献：
  名称：

  Fe(NO3)3·9H2O 在六氟异丙醇中对未活化芳烃进行后期 C-H 硝化

  摘要：

  使用廉价且易于获得的化学品进行操作简单且普遍适用的芳烃硝化一直是合成有机界长期以来寻求的转变。在这项工作中，我们以无毒且廉价的Fe(NO 3 ) 3 ·9H 2 O作为硝基源，并通过氢键相互作用网络以易于回收的溶剂六氟异丙醇作为促进剂实现了这一目标。由于该方案相对温和且可靠性高，实现了各种高功能化天然产物和市售药物的后期硝化。

  DOI：

  10.1021/acs.orglett.4c01006

文献信息

• Kinetics of 3-nitrotyrosine modification on exposure to hypochlorous acid
  作者：M. P. Curtis、J. W. Neidigh

  DOI：10.3109/10715762.2014.954110

  日期：2014.11

  The markers 3-nitrotyrosine and 3-chlorotyrosine are measured as surrogates for reactive nitrogen species and hypochlorous acid respectively, which are both elevated in inflamed human tissues. Previous studies reported a loss of 3-nitrotyrosine when exposed to hypochlorous acid, suggesting that observations of 3-nitrotyrosine underestimate the presence of reactive nitrogen species in diseased tissue (Whiteman and Halliwell, Biochemical and Biophysical Research Communications, 258, 168-172 (1999)). This report evaluates the significance of 3-nitrotyrosine loss by measuring the kinetics of the reaction between 3-nitrotyrosine and hypochlorous acid. The results demonstrate that 3-nitrotyrosine is chlorinated by hypochlorous acid or chloramines to form 3-chloro-5-nitrotyrosine. As 3-nitrotyrosine from in vivo samples is usually found within proteins rather than as free amino acid, we also examined the reaction of 3-nitrotyrosine modification in the context of peptides. The chlorination of 3-nitrotyrosine in peptides was observed to occur up to 700-fold faster than control reactions using equivalent amino acid mixtures. These results further advance our understanding of tyrosine chlorination and the use of 3-nitrotyrosine formed in vivo as a biomarker of reactive nitrogen species.
• 518. The synthesis of thyroxine and related compounds. Part XV. The preparation of thyronines from iodonium salts and derivatives of 3,5-disubstituted tyrosines
  作者：A. Dibbo、L. Stephenson、T. Walker、W. K. Warburton

  DOI：10.1039/jr9610002645

  日期：——
• Late-Stage C–H Nitration of Unactivated Arenes by Fe(NO₃)₃·9H₂O in Hexafluoroisopropanol
  作者：Yuzhu Zheng、Qi-Qi Hu、Qing Huang、Youwei Xie

  DOI：10.1021/acs.orglett.4c01006

  日期：2024.4.19

  Operationally simple and generally applicable arene nitration with cheap and easily accessible chemicals has been a long-sought transformation in the synthetic organic community. In this work, we realized this goal with nontoxic and inexpensive Fe(NO3)3·9H2O as the nitro source and easily recyclable solvent hexafluoroisopropanol as the promotor via a network of hydrogen-bonding interactions. As a result

  使用廉价且易于获得的化学品进行操作简单且普遍适用的芳烃硝化一直是合成有机界长期以来寻求的转变。在这项工作中，我们以无毒且廉价的Fe(NO 3 ) 3 ·9H 2 O作为硝基源，并通过氢键相互作用网络以易于回收的溶剂六氟异丙醇作为促进剂实现了这一目标。由于该方案相对温和且可靠性高，实现了各种高功能化天然产物和市售药物的后期硝化。