6-氟-3-羟基-1,2,3-苯并三嗪-4-酮 | 832127-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 中文名称: 6-氟-3-羟基-1,2,3-苯并三嗪-4-酮
• 英文名称: 6-fluoro-3-hydroxybenzo[d][1,2,3]triazin-4(3H)-one
• 英文别名: 3,4-dihydro-3-hydroxy-6-fluoro-4-oxo-1,2,3-benzotriazine；1,2,3-Benzotriazin-4(3H)-one, 6-fluoro-3-hydroxy-；6-fluoro-3-hydroxy-1,2,3-benzotriazin-4-one
• CAS: 832127-74-9
• 化学式: C₇H₄FN₃O₂
• 分子量: 181.126
• InChiKey: KJPCCGVLMVWQIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diphenyliodonium triflate 、 6-氟-3-羟基-1,2,3-苯并三嗪-4-酮 在 potassium tert-butylate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 以62%的产率得到6-fluoro-1-(2-hydroxyphenyl)benzo[1,2,3]triazin-4(1H)-one
  参考文献：
  名称：

  Tandem C–O and C–N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

  摘要：

  Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.

  DOI：

  10.1021/acs.joc.5b01947
• 作为产物：
  描述：

  2-氨基-5-氟苯甲酸 在 盐酸 、 ammonium hydroxide 、 硫酸 、 盐酸羟胺 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 96.5h， 生成 6-氟-3-羟基-1,2,3-苯并三嗪-4-酮
  参考文献：
  名称：

  Tandem C–O and C–N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

  摘要：

  Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.

  DOI：

  10.1021/acs.joc.5b01947

文献信息

• [EN] 3-HYDROXY-4-OXO-1,2,3-TRIAZINES AND DERIVATIVES THEREOF FOR AMIDE AND ESTER BOND FORMATION<br/>[FR] 3-HYDROXY-4-OXO-1,2,3-TRIAZINES ET LEURS DERIVES POUR LA FORMATION DE LIAISONS AMIDE ET ESTER
  申请人：FRUTAROM LTD

  公开号：WO2005007634A1

  公开（公告）日：2005-01-27

  The present invention relates to the use of a compound of formula I as a coupling reagent in forming amide or ester bonds from a reaction between a carboxylic acid and an amine or an alcohol, respectively. The compounds of formula I are especially useful as coupling reagents in the preparation of peptide bonds during peptide synthesis. In particular, the compounds of formula I are useful in promoting the formation of reactive reaction intermediates, inhibiting side reactions and in suppression of racemization. In addition, the present invention provides novel compounds of Formula I, and salts of N-oxides thereof.

  本发明涉及在羧酸与胺或醇之间的反应中，将式I化合物用作偶联试剂形成酰胺或酯键。式I化合物在肽合成过程中特别有用作为偶联试剂。具体来说，式I化合物有助于促进反应中间体的形成，抑制副反应和消除旋光异构化。此外，本发明提供了式I的新化合物及其N-氧化物盐。
• Tandem C–O and C–N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of <i>N</i>-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives
  作者：Wei-Min Shi、Xiao-Pan Ma、Cheng-Xue Pan、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1021/acs.joc.5b01947

  日期：2015.11.6

  Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.