2-(1,3-benzothiazol-2-yl)-3-[2-[tert-butyl(dimethyl)silyl]oxy-4-(diethylamino)phenyl]prop-2-enenitrile | 1401448-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(1,3-benzothiazol-2-yl)-3-[2-[tert-butyl(dimethyl)silyl]oxy-4-(diethylamino)phenyl]prop-2-enenitrile
• CAS: 1401448-31-4
• 化学式: C₂₆H₃₃N₃OSSi
• 分子量: 463.719
• InChiKey: MDKZHVHHJKMARU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(1,3-benzothiazol-2-yl)-3-[2-[tert-butyl(dimethyl)silyl]oxy-4-(diethylamino)phenyl]prop-2-enenitrile 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到3-(benzo[d]thiazol-2-yl)-N,N-diethyl-2-imino-2H-chromen-7-amine
  参考文献：
  名称：

  A Selective, Sensitive, Colorimetric, and Fluorescence Probe for Relay Recognition of Fluoride and Cu(II) Ions with “Off–On–Off” Switching in Ethanol–Water Solution

  摘要：

  Anion to cation relay recognition was designed and realized for the first time with sequence specificity (F--> Cu2+) via a fluorescence "off-on-off" mechanism. Probe 1 was a highly selective, sensitive, and turn-on chemodosimeter for F- through a specific cyclization reaction triggered by the strong affinity of fluoride toward silicon with a significant OFF change of fluorescence color in both ethanol and ethanol- water (1:1, v/v) solution. Fluorescence enhancement factors were dramatic: 833-fold in ethanol and 164-fold in ethanol-water (1:1, v/v) solution, respectively. The in situ system generated from the sensing of F- showed good relay recognition ability for Cu2+ via fast fluorescence quenching by the formation of a 1:1 complex in ethanol water (1:1, v/v) solution. The isolated pure compound 2 also exhibited high selectivity toward Cu2+. in PBS buffer (pH = 7.0) solution. The origin of this sequence specificity of fluorescence recognition was disclosed through the crystal or optimized structures and DFT calculations of corresponding compounds.

  DOI：

  10.1021/jo301548v
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 、 叔丁基二甲基氯硅烷 在 哌啶 、 咪唑 、 4-二甲氨基吡啶 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.33h， 生成 2-(1,3-benzothiazol-2-yl)-3-[2-[tert-butyl(dimethyl)silyl]oxy-4-(diethylamino)phenyl]prop-2-enenitrile
  参考文献：
  名称：

  A Selective, Sensitive, Colorimetric, and Fluorescence Probe for Relay Recognition of Fluoride and Cu(II) Ions with “Off–On–Off” Switching in Ethanol–Water Solution

  摘要：

  Anion to cation relay recognition was designed and realized for the first time with sequence specificity (F--> Cu2+) via a fluorescence "off-on-off" mechanism. Probe 1 was a highly selective, sensitive, and turn-on chemodosimeter for F- through a specific cyclization reaction triggered by the strong affinity of fluoride toward silicon with a significant OFF change of fluorescence color in both ethanol and ethanol- water (1:1, v/v) solution. Fluorescence enhancement factors were dramatic: 833-fold in ethanol and 164-fold in ethanol-water (1:1, v/v) solution, respectively. The in situ system generated from the sensing of F- showed good relay recognition ability for Cu2+ via fast fluorescence quenching by the formation of a 1:1 complex in ethanol water (1:1, v/v) solution. The isolated pure compound 2 also exhibited high selectivity toward Cu2+. in PBS buffer (pH = 7.0) solution. The origin of this sequence specificity of fluorescence recognition was disclosed through the crystal or optimized structures and DFT calculations of corresponding compounds.

  DOI：

  10.1021/jo301548v