4-Acetoxy-2,6-xylidin | 39942-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-Acetoxy-2,6-xylidin
• 英文别名: 4-Acetoxy-2.6-xylidin；4-Amino-3,5-dimethylphenyl acetate；(4-amino-3,5-dimethylphenyl) acetate
• CAS: 39942-44-4
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: REJOKVIJMOKWPZ-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Acetoxy-2,6-xylidin 在 lithium aluminium tetrahydride 、 乙酸酐 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.92h， 生成 N-(4-hydroxy-2,6-dimethylphenyl)-N-methylnitrous amide
  参考文献：
  名称：

  Photocontrollable Peroxynitrite Generator Based on N-Methyl-N-nitrosoaminophenol for Cellular Application

  摘要：

  We designed and synthesized a photocontrollable peroxynitrite (ONOO-) generator, P-NAP, which has N-methyl-N-nitrosoaminophenol structure with four methyl groups photodecomposition product with ONOO- and to lower the introduced onto the benzene ring to block reaction of the semiquinoneimine's redox potential. The semiquinoneimine intermediate generated by photoinduced release of nitric oxide (NO) reduces dissolved molecular oxygen to generate superoxide radical anion (O-2(center dot-)), which reacts with NO to afford ONOO- under diffusion control (k = 6.7 X 10(9) M-1 s(-1)). NO release from P-NAP under UV-A (330-380 nm) irradiation was confirmed by ESR spin trapping. Tyrosine nitration, characteristic of ONOO-, was demonstrated by HPLC analysis of a photoirradiated aqueous solution of P-NAP and N-acetyl-L-tyrosine ethyl ester. ONOO- formation was confirmed with a ONOO--specific fluorogenic probe, HKGreen-3, and compared with that from 3-(4-morpholinyl)sydnonimine hydrochloride (SIN-1), which is the most widely used ONOO- generator at present. The photoreaction of P-NAP was influenced by superoxide dismutase, indicating that generation of O-2(center dot-) occurs before ONOO- formation. The quantum yield for formation of duroquinone, the main P-NAP photodecomposition product, was measured as 0.86 +/- 0.07 at 334 nm with a potassium ferrioxalate actinometer. Generation of ONOO- from P-NAP in HCT-116 cells upon photoirradiation was successfully imaged with HKGreen-3A. This is the first example of a photocontrollable ONOO- donor applicable to cultured cells.

  DOI：

  10.1021/ja206744z
• 作为产物：
  描述：

  3,5-二甲基-4-氨基苯酚 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以65%的产率得到4-Acetoxy-2,6-xylidin
  参考文献：
  名称：

  Photocontrollable Peroxynitrite Generator Based on N-Methyl-N-nitrosoaminophenol for Cellular Application

  摘要：

  We designed and synthesized a photocontrollable peroxynitrite (ONOO-) generator, P-NAP, which has N-methyl-N-nitrosoaminophenol structure with four methyl groups photodecomposition product with ONOO- and to lower the introduced onto the benzene ring to block reaction of the semiquinoneimine's redox potential. The semiquinoneimine intermediate generated by photoinduced release of nitric oxide (NO) reduces dissolved molecular oxygen to generate superoxide radical anion (O-2(center dot-)), which reacts with NO to afford ONOO- under diffusion control (k = 6.7 X 10(9) M-1 s(-1)). NO release from P-NAP under UV-A (330-380 nm) irradiation was confirmed by ESR spin trapping. Tyrosine nitration, characteristic of ONOO-, was demonstrated by HPLC analysis of a photoirradiated aqueous solution of P-NAP and N-acetyl-L-tyrosine ethyl ester. ONOO- formation was confirmed with a ONOO--specific fluorogenic probe, HKGreen-3, and compared with that from 3-(4-morpholinyl)sydnonimine hydrochloride (SIN-1), which is the most widely used ONOO- generator at present. The photoreaction of P-NAP was influenced by superoxide dismutase, indicating that generation of O-2(center dot-) occurs before ONOO- formation. The quantum yield for formation of duroquinone, the main P-NAP photodecomposition product, was measured as 0.86 +/- 0.07 at 334 nm with a potassium ferrioxalate actinometer. Generation of ONOO- from P-NAP in HCT-116 cells upon photoirradiation was successfully imaged with HKGreen-3A. This is the first example of a photocontrollable ONOO- donor applicable to cultured cells.

  DOI：

  10.1021/ja206744z

文献信息

• Photocontrollable Peroxynitrite Generator Based on <i>N</i>-Methyl-<i>N</i>-nitrosoaminophenol for Cellular Application
  作者：Naoya Ieda、Hidehiko Nakagawa、Tao Peng、Dan Yang、Takayoshi Suzuki、Naoki Miyata

  DOI：10.1021/ja206744z

  日期：2012.2.8

  We designed and synthesized a photocontrollable peroxynitrite (ONOO-) generator, P-NAP, which has N-methyl-N-nitrosoaminophenol structure with four methyl groups photodecomposition product with ONOO- and to lower the introduced onto the benzene ring to block reaction of the semiquinoneimine's redox potential. The semiquinoneimine intermediate generated by photoinduced release of nitric oxide (NO) reduces dissolved molecular oxygen to generate superoxide radical anion (O-2(center dot-)), which reacts with NO to afford ONOO- under diffusion control (k = 6.7 X 10(9) M-1 s(-1)). NO release from P-NAP under UV-A (330-380 nm) irradiation was confirmed by ESR spin trapping. Tyrosine nitration, characteristic of ONOO-, was demonstrated by HPLC analysis of a photoirradiated aqueous solution of P-NAP and N-acetyl-L-tyrosine ethyl ester. ONOO- formation was confirmed with a ONOO--specific fluorogenic probe, HKGreen-3, and compared with that from 3-(4-morpholinyl)sydnonimine hydrochloride (SIN-1), which is the most widely used ONOO- generator at present. The photoreaction of P-NAP was influenced by superoxide dismutase, indicating that generation of O-2(center dot-) occurs before ONOO- formation. The quantum yield for formation of duroquinone, the main P-NAP photodecomposition product, was measured as 0.86 +/- 0.07 at 334 nm with a potassium ferrioxalate actinometer. Generation of ONOO- from P-NAP in HCT-116 cells upon photoirradiation was successfully imaged with HKGreen-3A. This is the first example of a photocontrollable ONOO- donor applicable to cultured cells.