2',3',6'-trifluoro-phenyl 1,6-dimethoxyacridine-9-carboxylate | 177535-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2',3',6'-trifluoro-phenyl 1,6-dimethoxyacridine-9-carboxylate
• 英文别名: (2,3,6-Trifluorophenyl) 1,6-dimethoxyacridine-9-carboxylate
• CAS: 177535-32-9
• 化学式: C₂₂H₁₄F₃NO₄
• 分子量: 413.353
• InChiKey: BPTHJNRDOMYZPT-UHFFFAOYSA-N

物化性质

• 沸点：
  611.8±55.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 2',3',6'-trifluoro-phenyl 1,6-dimethoxyacridine-9-carboxylate 以 二氯甲烷 为溶剂， 生成 Trifluoromethanesulfonate;(2,3,6-trifluorophenyl) 1,6-dimethoxy-10-methylacridin-10-ium-9-carboxylate
  参考文献：
  名称：

  Characterization of Acridancarboxylic Acid Derivatives as Chemiluminescent Peroxidase Substrates

  摘要：

  A new class of peroxidase substrates has been developed which produces chemiluminescence upon enzymatic oxidation. A wide variety of N-alkylacridancarboxylic acid derivatives including esters, thioesters, and sulfonamides are efficiently oxidized by a peroxidase and a peroxide to enzymatically produce the corresponding chemiluminescent acridinium compound, In conjunction with a peroxidase enhancer, continuous light emission with high light intensities and an extended duration are produced, Alternately, an appropriately designed acridan substrate produces a stable acridinium ester intermediate which can be accumulated and the chemiluminescence elicited as a burst of light by raising the pH. The effects of leaving groups and substitution on the acridan ring on the mechanism of light production are discussed, Peroxidase-catalyzed oxidation in the presence of a peroxide permits the detection of enzyme with subattomolar sensitivity and a broad linear dynamic range.

  DOI：

  10.1021/jo970202m
• 作为产物：
  描述：

  3’-甲氧基乙酰苯胺 在 吡啶 、 氢氧化钾 、 copper(l) iodide 、 三氯化铝 、 potassium carbonate 、 对甲苯磺酰氯 作用下， 反应 28.92h， 生成 2',3',6'-trifluoro-phenyl 1,6-dimethoxyacridine-9-carboxylate
  参考文献：
  名称：

  Characterization of Acridancarboxylic Acid Derivatives as Chemiluminescent Peroxidase Substrates

  摘要：

  A new class of peroxidase substrates has been developed which produces chemiluminescence upon enzymatic oxidation. A wide variety of N-alkylacridancarboxylic acid derivatives including esters, thioesters, and sulfonamides are efficiently oxidized by a peroxidase and a peroxide to enzymatically produce the corresponding chemiluminescent acridinium compound, In conjunction with a peroxidase enhancer, continuous light emission with high light intensities and an extended duration are produced, Alternately, an appropriately designed acridan substrate produces a stable acridinium ester intermediate which can be accumulated and the chemiluminescence elicited as a burst of light by raising the pH. The effects of leaving groups and substitution on the acridan ring on the mechanism of light production are discussed, Peroxidase-catalyzed oxidation in the presence of a peroxide permits the detection of enzyme with subattomolar sensitivity and a broad linear dynamic range.

  DOI：

  10.1021/jo970202m

文献信息

• NOVEL METHOD AND KITS FOR PRODUCING LIGHT FROM AN ACRIDAN COMPOUND
  申请人：LUMIGEN, INC.

  公开号：EP0778946B1

  公开（公告）日：2002-10-23
• US5670644A
  申请人：——

  公开号：US5670644A

  公开（公告）日：1997-09-23
• US5723295A
  申请人：——

  公开号：US5723295A

  公开（公告）日：1998-03-03
• Characterization of Acridancarboxylic Acid Derivatives as Chemiluminescent Peroxidase Substrates
  作者：Hashem Akhavan-Tafti、Renuka DeSilva、Zahra Arghavani、Robert A. Eickholt、Richard S. Handley、Barry A. Schoenfelner、Katsuaki Sugioka、Yumiko Sugioka、A. Paul Schaap

  DOI：10.1021/jo970202m

  日期：1998.2.1

  A new class of peroxidase substrates has been developed which produces chemiluminescence upon enzymatic oxidation. A wide variety of N-alkylacridancarboxylic acid derivatives including esters, thioesters, and sulfonamides are efficiently oxidized by a peroxidase and a peroxide to enzymatically produce the corresponding chemiluminescent acridinium compound, In conjunction with a peroxidase enhancer, continuous light emission with high light intensities and an extended duration are produced, Alternately, an appropriately designed acridan substrate produces a stable acridinium ester intermediate which can be accumulated and the chemiluminescence elicited as a burst of light by raising the pH. The effects of leaving groups and substitution on the acridan ring on the mechanism of light production are discussed, Peroxidase-catalyzed oxidation in the presence of a peroxide permits the detection of enzyme with subattomolar sensitivity and a broad linear dynamic range.