4,7-dichloro-5-hydroxy-3,3-dimethylbenzofuran-2(3H)-one | 1621232-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 4,7-dichloro-5-hydroxy-3,3-dimethylbenzofuran-2(3H)-one
• 英文别名: 4,7-Dichloro-5-hydroxy-3,3-dimethyl-1-benzofuran-2-one
• CAS: 1621232-70-9
• 化学式: C₁₀H₈Cl₂O₃
• 分子量: 247.078
• InChiKey: KIYUSUVRZOAELW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 2,5-二氯-1,4-苯醌 以 二氯甲烷 为溶剂， 反应 14.0h， 以18%的产率得到4,7-dichloro-2-methoxy-3,3-dimethyl-2-(trimethylsilyloxy)-2,3-dihydrobenzofuran-5-ol
  参考文献：
  名称：

  Quantification of the Ambident Electrophilicities of Halogen-Substituted Quinones

  摘要：

  Kinetics and mechanisms of the reactions of p-quinone, 2,5-dichloro-p-quinone, 2,3,4,5-tetrachloro-p-quinone (chloranil), 2,3,4,5-tetrafluoro-p-quinone (fluoranil), and 3,4,5,6-tetrachloro-o-quinone with pi-nudeophiles (siloxyalkenes, enamines) and amines have been investigated. Products arising from nudeophilic attack at all conceivable sites, that is, at C and O of the carbonyl groups (pathways a, b) as well as at halogenated and nonhalogenated conjugate positions (pathways c, d), were observed. The partial rate constants for the C-attack pathways (a, c, d), which are derived from the photometrically determined second-order rate constants and the product ratios followed the linear free energy relationship log k (20 degrees C) = s(N)(E + (Mayr, H.; et al. J. Am. Chem. Soc. 2001, 123, 9500-9512). It was, therefore, possible to calculate the electrophilicity parameters E of the different positions of the quinones from log k (20 degrees C) and the N and s(N) parameters of the nucleophilic reaction partners, which have previously been derived from their reactions with benzhydrylium ions. Almost all rate constants for the C-attack pathways (a, c, d) were considerably larger than those calculated for the corresponding SET processes, indicating the operation of polar mechanisms. SET mechanisms may only account for the formation of the products formed via O-attack. With the E parameters determined in this work, it is now possible to predict rate constants for the reactions of these quinones with a large variety of nudeophiles and, thus, envisage unprecedented reactions of quinones.

  DOI：

  10.1021/ja505613b