2-bromo-5-methoxy-4,6-dimethyl-3-pyridinol | 1062541-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-5-methoxy-4,6-dimethyl-3-pyridinol
• 英文别名: 2-Bromo-5-methoxy-4,6-dimethylpyridin-3-ol；2-bromo-5-methoxy-4,6-dimethylpyridin-3-ol
• CAS: 1062541-76-7
• 化学式: C₈H₁₀BrNO₂
• 分子量: 232.077
• InChiKey: MFXKEZYXDFMXCS-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  359.2±37.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-bromo-5-methoxy-4,6-dimethyl-3-pyridinol 在 叔丁基锂 、 碲化氢 、 air 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 生成
  参考文献：
  名称：

  Catalytic Chain-Breaking Pyridinol Antioxidants

  摘要：

  When assayed for their capacity to inhibit azo-initiated peroxidation of linoleic acid in a water/chlorobenzene two-phase system, tellurium-containing 3-pyridinols were readily regenerable by N-acetylcysteine contained in the aqueous phase. The best inhibitors quenched peroxyl radicals more efficiently than alpha-tocopherol, and the duration of inhibition was limited only by the availability of the thiol reducing agent. The compounds were also found to catalyze reduction of hydrogen peroxide in the presence of thiol reducing agent.

  DOI：

  10.1021/ol801983n
• 作为产物：
  描述：

  3-amino-2-bromo-5-methoxy-4,6-dimethylpyridine 在 tetrafluoroboric acid 、 水 、 sodium nitrite 作用下， 以 水 为溶剂， 以54%的产率得到2-bromo-5-methoxy-4,6-dimethyl-3-pyridinol
  参考文献：
  名称：

  Catalytic Chain-Breaking Pyridinol Antioxidants

  摘要：

  The synthesis of 3-pyridinols carrying alkyltelluro, alkylseleno, and alkylthio groups is described together with a detailed kinetic, thermodynamic, and mechanistic Study of their antioxidant activity. When assayed for their capacity to inhibit azo-initiated peroxidation of linoleic acid in a water/chlorobenzene two-phase system, tellurium-containing 3-pyridinols were readily regenerable by N-acetylcysteine contained in the aqueous phase. The best inhibitors quenched peroxyl radicals more efficiently than alpha-tocopherol, and the duration of inhibition was limited only by the availability of the thiol reducing agent. fn homogeneous phase, inhibition of styrene autoxidation absolute rate constants k(inh) for quenching of peroxyl radical were as large as 1 x 10(7) M-1 s(-1), thus Outperforming the best phenolic antioxidants including alpha-tocopherol. Tellurium-containing 3-pyridinols could be quantitatively regenerated in homogeneous phase by N-tert-butoxycarbonyl cysteine methyl ester, a lipid-soluble analogue of N-acetylcysteine. In the presence of an excess of the thiol, a catalytic mode of action was observed, similar to the one in the two-phase system. Overall, compounds bearing the alkyltelluro moiety ortho to the OH group were much more effective antioxidants than the corresponding para isomers. The origin of the high reactivity of these compounds was explored using pulse-radiolysis thermodynamic measurements, and a mechanism for their unusual antioxidant activity was proposed. The tellurium-containing 3-pyridinols were also found to catalyze reduction of hydrogen peroxide in the presence of thiol reducing agents, thereby acting as multifunctional (preventive and chain-breaking) catalytic antioxidants.

  DOI：

  10.1021/jo902226t

文献信息

• [EN] COMPOUNDS COMPRISING A 3-PYRIDINOL OR 5-PYRIMIDINOL RING HAVING AN ORGANOSELENO OR ORGANOTELLURO SUBSTITUENT FOR USE AS ANTIOXIDANTS<br/>[FR] COMPOSÉS COMPRENANT UN NOYAU 3-PYRIDINOL OU 5-PYRIMIDINOL À SUBSTITUANT ORGANOSÉLÉNO OU ORGANOTELLURO UTILISÉS COMME ANTI-OXYDANTS
  申请人：KAROLINSKA INST INNOVATIONS AB

  公开号：WO2009144253A1

  公开（公告）日：2009-12-03

  Compounds comprising a 3-pyridinol or 5-pyrimidinol ring carrying an organoseleno- or organotelluro- substituent on the pyridine or pyrimidine ring, exhibit useful antioxidant properties. The compounds may for example be in accordance with the following formula (I) as defined herein. Catalytic chain-breaking and hydroperoxide decomposing antioxidant properties are also disclosed. Furthermore the compounds may be used in combination with a reducing agent. The compounds are useful for the stabilization of man-made and natural materials, or for the prevention or treatment of disorders caused by or involving free radical-mediated or oxidative tissue damage.

  含有3-吡啶醇或5-嘧啶醇环，在吡啶或嘧啶环上带有有机硒或有机碲取代基团的化合物，表现出有用的抗氧化性能。这些化合物可能符合以下定义的化学式(I)。还披露了催化链断裂和过氧化物分解抗氧化性能。此外，这些化合物可以与还原剂结合使用。这些化合物可用于稳定人造和天然材料，或用于预防或治疗由自由基介导或氧化组织损伤引起的疾病。
• Catalytic Chain-Breaking Pyridinol Antioxidants
  作者：Sangit Kumar、Henrik Johansson、Takahiro Kanda、Lars Engman、Thomas Müller、Helena Bergenudd、Mats Jonsson、Gian Franco Pedulli、Riccardo Amorati、Luca Valgimigli

  DOI：10.1021/jo902226t

  日期：2010.2.5

  The synthesis of 3-pyridinols carrying alkyltelluro, alkylseleno, and alkylthio groups is described together with a detailed kinetic, thermodynamic, and mechanistic Study of their antioxidant activity. When assayed for their capacity to inhibit azo-initiated peroxidation of linoleic acid in a water/chlorobenzene two-phase system, tellurium-containing 3-pyridinols were readily regenerable by N-acetylcysteine contained in the aqueous phase. The best inhibitors quenched peroxyl radicals more efficiently than alpha-tocopherol, and the duration of inhibition was limited only by the availability of the thiol reducing agent. fn homogeneous phase, inhibition of styrene autoxidation absolute rate constants k(inh) for quenching of peroxyl radical were as large as 1 x 10(7) M-1 s(-1), thus Outperforming the best phenolic antioxidants including alpha-tocopherol. Tellurium-containing 3-pyridinols could be quantitatively regenerated in homogeneous phase by N-tert-butoxycarbonyl cysteine methyl ester, a lipid-soluble analogue of N-acetylcysteine. In the presence of an excess of the thiol, a catalytic mode of action was observed, similar to the one in the two-phase system. Overall, compounds bearing the alkyltelluro moiety ortho to the OH group were much more effective antioxidants than the corresponding para isomers. The origin of the high reactivity of these compounds was explored using pulse-radiolysis thermodynamic measurements, and a mechanism for their unusual antioxidant activity was proposed. The tellurium-containing 3-pyridinols were also found to catalyze reduction of hydrogen peroxide in the presence of thiol reducing agents, thereby acting as multifunctional (preventive and chain-breaking) catalytic antioxidants.