2,2,2-trifluoro-N-(3-(hydroxy(phenyl)methyl)-4-(phenyldiazenyl)phenyl)acetamide | 1312575-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2,2,2-trifluoro-N-(3-(hydroxy(phenyl)methyl)-4-(phenyldiazenyl)phenyl)acetamide
• CAS: 1312575-12-4
• 化学式: C₂₁H₁₆F₃N₃O₂
• 分子量: 399.372
• InChiKey: AYDMMSPYCKBAKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.05
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 、 2,2,2-trifluoro-N-(3-(hydroxy(phenyl)methyl)-4-(phenyldiazenyl)phenyl)acetamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以88%的产率得到(2R,3R,4S,5R)-2-(acetoxymethyl)-6-(phenyl(2-(phenyldiazenyl)-5-(2,2,2-trifluoroacetamido)phenyl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  A novel cyanide chemodosimeter based on trifluoroacetamide benzhydrol-2 as binding motif: importance of substituent positioning on intra-molecular charge transfer

  摘要：

  The nucleophilic nature of cyanide is used to develop a simple, sensitive, and highly effective sensor. Azo dye 6a based on 2-(trifluoroacetamide) benzhydrol-2 (2-TFAB) as anions receptor, presents a new way to build molecular color sensors for cyanide in water. The 2-TFAB moiety of the dye 6a is used as receptor group for cyanides and linked directly by dominant reversible covalent bonding over hydrogen bonding, confirmed by the inactivity of the derivative 6b toward cyanides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.059
• 作为产物：
  描述：

  3-氨基苯基苯甲酮 在 盐酸 、 sodium tetrahydroborate 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 7.5h， 生成 2,2,2-trifluoro-N-(3-(hydroxy(phenyl)methyl)-4-(phenyldiazenyl)phenyl)acetamide
  参考文献：
  名称：

  A novel cyanide chemodosimeter based on trifluoroacetamide benzhydrol-2 as binding motif: importance of substituent positioning on intra-molecular charge transfer

  摘要：

  The nucleophilic nature of cyanide is used to develop a simple, sensitive, and highly effective sensor. Azo dye 6a based on 2-(trifluoroacetamide) benzhydrol-2 (2-TFAB) as anions receptor, presents a new way to build molecular color sensors for cyanide in water. The 2-TFAB moiety of the dye 6a is used as receptor group for cyanides and linked directly by dominant reversible covalent bonding over hydrogen bonding, confirmed by the inactivity of the derivative 6b toward cyanides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.059