3-tert-Butyl-4,5-dihydroxybenzoesaeure-ethylester | 81056-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-tert-Butyl-4,5-dihydroxybenzoesaeure-ethylester
• 英文别名: ethyl 5-tert-butyl-3,4-dihydroxybenzoate；3,4-Dihydroxy-5-tert.-butyl-benzoesaeureaethylester；Ethyl 3-tert-butyl-4,5-dihydroxybenzoate
• CAS: 81056-45-3
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: FEWHFNDXRXXGBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  385.8±42.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二-叔-丁基-4-羟基苯甲酸乙酯 在 Co(II)(Salpr) 二甲基硫 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-tert-Butyl-4,5-dihydroxybenzoesaeure-ethylester
  参考文献：
  名称：

  Novel tert-Butyl Migration in Copper-Mediated Phenol Ortho-Oxygenation Implicates a Mechanism Involving Conversion of a 6-Hydroperoxy-2,4-cyclohexadienone Directly to an o-Quinone

  摘要：

  Copper mediated ortho-oxygenation of phenolates may proceed through the generation of a 6-peroxy-2,4-cyclohexadienone intermediate. To test this theory, we studied the fate of sodium 4-carbethoxy2,6-di-tert-butylphenolate, where the ortho-oxygenation sites are blocked by tert-butyl groups. Using the Cu(I) complex of N,N-bis(2-(N-methylbenzimidazol-2-yl)ethyl)benzylamine, isolation of the major oxygenated product and characterization by single-crystal X-ray crystallography and NMR spectroscopy revealed it to be 4-carbethoxy-3,6-di-tert-butyl-1,2-benzoquinone, resulting from a 1,2-migration of a tert-butyl group. The independently prepared B-hydroperoxide is transformed by the Cu(I)- (or Cu(II)-) ligand complex to the same o-quinone. The observed 1,2-migration of the tert-butyl group appears to reflect an electron demand created by rearrangement of the postulated peroxy intermediate. A mechanism proceeding alternatively through a catechol and subsequent oxidation to the o-quinone seems ruled out by a control study demonstrating that the requisite intermediate to catechol formation would instead eliminate the 2-tert-butyl group.

  DOI：

  10.1021/jo991625m

文献信息

• Dreher, Eberhard-Ludwig; Bracht, Juergen; El-Mobayed, Medhat, Chemische Berichte, 1982, vol. 115, # 1, p. 288 - 308
  作者：Dreher, Eberhard-Ludwig、Bracht, Juergen、El-Mobayed, Medhat、Huetter, Peter、Winter, Werner、Rieker, Anton

  DOI：——

  日期：——