3,5-dimethylquinone-1-imine | 4370-74-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,5-dimethylquinone-1-imine
• 英文别名: 4-imino-2,6-dimethylcyclohexa-2,5-dien-1-one；2,6-Dimethylbenzochinonimin；2,6-Dimethyl-p-benzochinonmonoimin
• CAS: 4370-74-5
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: ISDOHCQSDKUSMT-UHFFFAOYSA-N

物化性质

• 沸点：
  234.7±33.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dimethylquinone-1-imine 在 维生素 C 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 生成 N^α-(tert-butoxycarbonyl)-N^ε-(4-hydroxy-3,5-dimethylphenyl)lysine
  参考文献：
  名称：

  Transimination of Quinone Imines: A Mechanism for Embedding Exogenous Redox Activity into the Nucleosome

  摘要：

  Aminophenols can redox cycle through the corresponding quinone imines to generate ROS. The electrophilic quinone imine intermediate can react with protein thiols as a mechanism of immobilization in vivo. Here, we describe the previously unkown transimination of a quinone imine by lysine as an alternative anchoring mechanism. The redox properties of the condensation product remain largely unchanged because the only structural change to the redox nucleus is the addition of an alkyl substituent to the imine nitrogen. Transimination enables targeting of histone proteins since histones are lysine-rich but nearly devoid of cysteines. Consequently, quinone imines can be embedded in the nucleosome and may be expected to produce ROS in maximal proximity to the genome.

  DOI：

  10.1021/tx3004517
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 在 亚甲兰 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、1.0 MPa 条件下， 反应 0.67h， 以68%的产率得到3,5-dimethylquinone-1-imine
  参考文献：
  名称：

  可见光连续流光反应器中苯酚的有机光催化有氧氧化

  摘要：

  本文描述了通过使用可见光和加压空气的连续流动光反应器实现的温和光催化苯酚氧化。通过精确控制主要工艺参数，以高产率获得了广泛应用的产品，包括合成维生素。反应器设计允许低有机光催化剂负载以产生单线态氧。预计有效的有氧苯酚氧化成苯醌和对羟基苯酚有助于可持续合成。

  DOI：

  10.1002/chem.202101313

文献信息

• Organophotocatalytic Aerobic Oxygenation of Phenols in a Visible‐Light Continuous‐Flow Photoreactor
  作者：Joël Wellauer、Dragan Miladinov、Thomas Buchholz、Jan Schütz、René T. Stemmler、Jonathan A. Medlock、Werner Bonrath、Christof Sparr

  DOI：10.1002/chem.202101313

  日期：2021.7.7

  A mild photocatalytic phenol oxygenation enabled by a continuous-flow photoreactor using visible light and pressurized air is described herein. Products for wide-ranging applications, including the synthesis of vitamins, were obtained in high yields by precisely controlling principal process parameters. The reactor design permits low organophotocatalyst loadings to generate singlet oxygen. It is anticipated

  本文描述了通过使用可见光和加压空气的连续流动光反应器实现的温和光催化苯酚氧化。通过精确控制主要工艺参数，以高产率获得了广泛应用的产品，包括合成维生素。反应器设计允许低有机光催化剂负载以产生单线态氧。预计有效的有氧苯酚氧化成苯醌和对羟基苯酚有助于可持续合成。
• Transimination of Quinone Imines: A Mechanism for Embedding Exogenous Redox Activity into the Nucleosome
  作者：Wenjie Ye、Uthpala I. Seneviratne、Ming-Wei Chao、Kodihalli C. Ravindra、Gerald N. Wogan、Steven R. Tannenbaum、Paul L. Skipper

  DOI：10.1021/tx3004517

  日期：2012.12.17

  Aminophenols can redox cycle through the corresponding quinone imines to generate ROS. The electrophilic quinone imine intermediate can react with protein thiols as a mechanism of immobilization in vivo. Here, we describe the previously unkown transimination of a quinone imine by lysine as an alternative anchoring mechanism. The redox properties of the condensation product remain largely unchanged because the only structural change to the redox nucleus is the addition of an alkyl substituent to the imine nitrogen. Transimination enables targeting of histone proteins since histones are lysine-rich but nearly devoid of cysteines. Consequently, quinone imines can be embedded in the nucleosome and may be expected to produce ROS in maximal proximity to the genome.