3-(cis-4-tert-butylcyclohexyl)-3-(2-(cis-4-tert-butylcyclohexyl)naphtho-1,4-quinon-3-yl)oxy-2-oxo-2,3-dihydronaphtho-1,4-quinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(cis-4-tert-butylcyclohexyl)-3-(2-(cis-4-tert-butylcyclohexyl)naphtho-1,4-quinon-3-yl)oxy-2-oxo-2,3-dihydronaphtho-1,4-quinone
• 英文别名: 3-(4-Tert-butylcyclohexyl)-3-[3-(4-tert-butylcyclohexyl)-1,4-dioxonaphthalen-2-yl]oxynaphthalene-1,2,4-trione
• 化学式: C₄₀H₄₆O₆
• 分子量: 622.802
• InChiKey: AZFKARCRIHKFAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 2-(顺式-4-叔丁基环己基)-3-羟基萘-1,4-醌 在 (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 以3%的产率得到3-(cis-4-tert-butylcyclohexyl)-3-(2-(cis-4-tert-butylcyclohexyl)naphtho-1,4-quinon-3-yl)oxy-2-oxo-2,3-dihydronaphtho-1,4-quinone
  参考文献：
  名称：

  Metalloporphyrin-Catalyzed Oxidation of 2-Cycloalkyl-3-hydroxynaphthoquinones

  摘要：

  Mild H2O2 oxidation of a small series of 2-cycloalkyl-3-hydroxynaphthoquinones catalyzed by 5,-10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphineiron(III) chloride in methanol-dichloromethane leads in each case to the isolation of a dehydro-dimer identified as a 3-cycloalkyl-3-(2-cycloalkylnaphthoquinon-3-yl)oxy-2-oxo-2,3-dihydronaphtho-1,4-quinone and in some cases to a 2-cycloalkyl-2,3-dihydroxy-1-oxoindan-3-carboxylate. The mechanism of formation of the former is rationalized in terms of nucleophilic attack of unreacted hydroxynaphthoquinone anion upon an epoxide primary oxidation product, while that of the latter is proposed to involve nucleophilic attack of solvent methanal on the same epoxide followed by rearrangement.

  DOI：

  10.1021/jo990297n

文献信息

• Metalloporphyrin-Catalyzed Oxidation of 2-Cycloalkyl-3-hydroxynaphthoquinones
  作者：Ian D. Cunningham、Timothy N. Danks、Keith T. A. O'Connell、Peter W. Scott

  DOI：10.1021/jo990297n

  日期：1999.10.1

  Mild H2O2 oxidation of a small series of 2-cycloalkyl-3-hydroxynaphthoquinones catalyzed by 5,-10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphineiron(III) chloride in methanol-dichloromethane leads in each case to the isolation of a dehydro-dimer identified as a 3-cycloalkyl-3-(2-cycloalkylnaphthoquinon-3-yl)oxy-2-oxo-2,3-dihydronaphtho-1,4-quinone and in some cases to a 2-cycloalkyl-2,3-dihydroxy-1-oxoindan-3-carboxylate. The mechanism of formation of the former is rationalized in terms of nucleophilic attack of unreacted hydroxynaphthoquinone anion upon an epoxide primary oxidation product, while that of the latter is proposed to involve nucleophilic attack of solvent methanal on the same epoxide followed by rearrangement.