5-(tert-butyl)-2-hydroxy-3-((hydroxyimino)methyl)benzaldehyde | 1440207-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(tert-butyl)-2-hydroxy-3-((hydroxyimino)methyl)benzaldehyde
• CAS: 1440207-64-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: VUNNNCLXMFOWEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.89
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(tert-butyl)-2-hydroxy-3-((hydroxyimino)methyl)benzaldehyde 、 1,2,3,3-四甲基-3H-吲哚鎓碘化物 在 吗啉 作用下， 以 乙醇 为溶剂， 以82%的产率得到6-(tert-butyl)-1',3',3'-trimethylspiro[chromene-2,2'-indoline]-8-carbaldehyde oxime
  参考文献：
  名称：

  Ratiometric pH responsive fluorescent probes operative on ESIPT

  摘要：

  A series of C-8'-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilitate the subsequent enol-keto tautomerization giving dual emissive peaks via the excited state intramolecular proton transfer (ESIPT) mechanism. The pH titrations of 4a show a 68-fold increase in ratiometric intensities ratio (I-645 nm/I-522 (nm)) when the pH was switched from 8.0 to 4.0 with a pK(a) value of 5.90. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.023
• 作为产物：
  描述：

  4-叔丁基-2,6-二甲酰基苯酚 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以38%的产率得到5-(tert-butyl)-2-hydroxy-3-((hydroxyimino)methyl)benzaldehyde
  参考文献：
  名称：

  Ratiometric pH responsive fluorescent probes operative on ESIPT

  摘要：

  A series of C-8'-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilitate the subsequent enol-keto tautomerization giving dual emissive peaks via the excited state intramolecular proton transfer (ESIPT) mechanism. The pH titrations of 4a show a 68-fold increase in ratiometric intensities ratio (I-645 nm/I-522 (nm)) when the pH was switched from 8.0 to 4.0 with a pK(a) value of 5.90. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.023