(2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-(5-methoxy-3,4-dioxocyclohexa-1,5-diene-1-carbonyl)oxypropanoic acid | 246047-89-2

• 英文名称: (2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-(5-methoxy-3,4-dioxocyclohexa-1,5-diene-1-carbonyl)oxypropanoic acid
• CAS: 246047-89-2
• 化学式: C₂₃H₂₂N₂O₉S
• 分子量: 502.502
• InChiKey: RKXSDVOIVPJYON-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  邻苯二胺 、 (2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-(5-methoxy-3,4-dioxocyclohexa-1,5-diene-1-carbonyl)oxypropanoic acid 在 溶剂黄146 作用下， 以26%的产率得到
  参考文献：
  名称：

  Probing the Role of Polyphenol Oxidation in Mediating Insect−Pathogen Interactions. Galloyl-Derived Electrophilic Traps for the Lymantria dispar Nuclear Polyhedrosis Virus Matrix Protein Polyhedrin

  摘要：

  Galloyl-derived orthoquinone probes have been designed, synthesized, and utilized in an ongoing study of insect-pathogen interactions. A stable galloyl-derived orthoquinone O-methyl ether modified with both acidic and fluorescent appendages was successful in trapping the model nucleophile cysteine, a test protein bearing a single cysteine residue, and the viral occlusion body matrix protein polyhedrin from Lymantria dispar nuclear polyhedrosis virus (LdNPV), a pathogen of the gypsy moth caterpillar (GMc). This latter observation may be related to the molecular mechanism by which gallotannins decrease LdNPV infectivity in GMc's. Sufficient site isolation was not achieved with a polymer-bound reactive galloyl hydroxyorthoquinone electrophile to permit similar nucleophile trapping to compete with oligomerization.

  DOI：

  10.1021/jo982477n
• 作为产物：
  描述：

  丹酰氯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 邻四氯苯醌 、 氢气 、 碳酸氢钠 、 达卡巴嗪 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， -42.0~20.0 ℃ 、101.33 kPa 条件下， 反应 40.5h， 生成 (2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-(5-methoxy-3,4-dioxocyclohexa-1,5-diene-1-carbonyl)oxypropanoic acid
  参考文献：
  名称：

  Probing the Role of Polyphenol Oxidation in Mediating Insect−Pathogen Interactions. Galloyl-Derived Electrophilic Traps for the Lymantria dispar Nuclear Polyhedrosis Virus Matrix Protein Polyhedrin

  摘要：

  Galloyl-derived orthoquinone probes have been designed, synthesized, and utilized in an ongoing study of insect-pathogen interactions. A stable galloyl-derived orthoquinone O-methyl ether modified with both acidic and fluorescent appendages was successful in trapping the model nucleophile cysteine, a test protein bearing a single cysteine residue, and the viral occlusion body matrix protein polyhedrin from Lymantria dispar nuclear polyhedrosis virus (LdNPV), a pathogen of the gypsy moth caterpillar (GMc). This latter observation may be related to the molecular mechanism by which gallotannins decrease LdNPV infectivity in GMc's. Sufficient site isolation was not achieved with a polymer-bound reactive galloyl hydroxyorthoquinone electrophile to permit similar nucleophile trapping to compete with oligomerization.

  DOI：

  10.1021/jo982477n