3-tert-butyl-5-isopropylsulfanylsalicylaldehyde | 1373999-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-tert-butyl-5-isopropylsulfanylsalicylaldehyde
• CAS: 1373999-41-7
• 化学式: C₁₄H₂₀O₂S
• 分子量: 252.378
• InChiKey: OACDJMHHMZVLNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  325.0±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-tert-butyl-5-isopropylsulfanylsalicylaldehyde 、 N-(3-tert-butyl-2-hydroxy-5-methoxybenzylidene)-trans-1,2-diaminocyclohexane hydrochloride 在 三乙胺 作用下， 以 甲醇 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  Electrochemical and Spectroscopic Effects of Mixed Substituents in Bis(phenolate)–Copper(II) Galactose Oxidase Model Complexes

  摘要：

  Nonsymmetric substitution of salen (1(R1,R2)) and reduced salen (2(R1,R2)) Cu-II-phenoxyl complexes with a combination of -Bu-t, -(SPr)-Pr-i, and -OMe substituents leads to dramatic differences in their redox and spectroscopic properties, providing insight into the influence of the cysteine-modified tyrosine cofactor in the enzyme galactose oxidase (GO). Using a modified Marcus-Hush analysis, the oxidized copper complexes are characterized as Class II mixed-valent due to the electronic differentiation between the two substituted phenolates. Sulfur K-edge X-ray absorption spectroscopy (XAS) assesses the degree of radical delocalization onto the single sulfur atom of nonsymmetric [1(tBu,SMe)](+) at 7%, consistent with other spectroscopic and electrochemical results that suggest preferential oxidation of the -SMe bearing phenolate. Estimates of the thermodynamic free energy difference between the two localized states (Delta G degrees) and reorganizational energies (lambda(R1R2)) of [1(R1,R2)](+) and [2(R1,R2)](+) lead to accurate predictions of the spectroscopically observed IVCT transition energies. Application of the modified Marcus-Hush analysis to GO using parameters determined for [2(R1,R2)](+) predicts a nu(max) of similar to 43600 cm(-1), well within the energy range of the broad Vis-NIR band displayed by the enzyme.

  DOI：

  10.1021/ja211247f