2,6-Ditert-butyl-4,4-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]cyclohexa-2,5-dien-1-one | 62078-82-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,6-Ditert-butyl-4,4-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]cyclohexa-2,5-dien-1-one
• CAS: 62078-82-4
• 化学式: C₄₄H₆₆O₃
• 分子量: 643.006
• InChiKey: RMDQNDGDHVFELV-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C (decomp)
• 沸点：
  644.6±55.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二叔丁基-4-溴甲基苯酚 在 抗氧剂 702 、 三乙胺 作用下， 以 正戊烷 为溶剂， 生成 2,6-Ditert-butyl-4,4-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]cyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Reinvestigation of the reaction of 2,6-di-tert-butylbenzoquinone methide and 2,6-di-tert-butylphenol

  摘要：

  The reaction of quinone methide 1 and phenol 2 in equimolar amounts was investigated in pentane at 30-degrees-C. Products were isolated by means of column chromatography on SiO2. There was a marked difference in product distribution between the reactions in the presence and absence of added Et3N. Dienones 3 and 10 were obtained only from the former reaction, while formation of 1,2-bis(4-hydroxyphenyl)ethane 18 and 4,4'-dihydroxybiphenyl 20 was overwhelming in the latter reaction. Other products from both reactions were relatively small quantities of 4,4'-stilbenequinone 17, 4,4'-diphenoquinone 21, and bis(4-hydroxyphenyl)methane 24, but dienone 4 was not obtained. Compounds 20 and 24 obtained from the latter reaction were formed by isomerization of dienones 19 and 23, respectively, during the chromatography. The reaction is initiated by dimerization of 1 to generate biradical 11. Subsequent processes involving hydrogenation-dehydrogenation, coupling-dissociation, and dienone-phenol rearrangement account for the formation or the lack of formation of the products. The difference in product distribution is ascribed to capability of Et3N to catalyze the isomerization. Quinone methide 1 also adds to 2 to give 23. The decay of 1 in the presence of both 2 and phenol 6 gave dienone 8 additionally. The formation of 24 and 4 was facilitated by conducting the reaction of 1 and 2 in DMSO. Dehydrogenation of 10 and 3 with PbO2 afforded spirodienones 27 and 28, respectively. Compounds 27 and 28 were unstable, and their decay in solution was investigated in the presence or absence of added 2. The results show that the decay is initiated by homolytic scission of the C-C bond connecting the dienone rings in the cyclopentane (in 27) and cyclohexane (in 28) rings. Compound 28 is novel in that it bears two kinds of such C-C bonds. Reversibility of the dimerization of 1 is suggested.

  DOI：

  10.1021/jo00027a053

文献信息

• Reinvestigation of the reaction of 2,6-di-tert-butylbenzoquinone methide and 2,6-di-tert-butylphenol
  作者：Kanji Omura

  DOI：10.1021/jo00027a053

  日期：1992.1

  The reaction of quinone methide 1 and phenol 2 in equimolar amounts was investigated in pentane at 30-degrees-C. Products were isolated by means of column chromatography on SiO2. There was a marked difference in product distribution between the reactions in the presence and absence of added Et3N. Dienones 3 and 10 were obtained only from the former reaction, while formation of 1,2-bis(4-hydroxyphenyl)ethane 18 and 4,4'-dihydroxybiphenyl 20 was overwhelming in the latter reaction. Other products from both reactions were relatively small quantities of 4,4'-stilbenequinone 17, 4,4'-diphenoquinone 21, and bis(4-hydroxyphenyl)methane 24, but dienone 4 was not obtained. Compounds 20 and 24 obtained from the latter reaction were formed by isomerization of dienones 19 and 23, respectively, during the chromatography. The reaction is initiated by dimerization of 1 to generate biradical 11. Subsequent processes involving hydrogenation-dehydrogenation, coupling-dissociation, and dienone-phenol rearrangement account for the formation or the lack of formation of the products. The difference in product distribution is ascribed to capability of Et3N to catalyze the isomerization. Quinone methide 1 also adds to 2 to give 23. The decay of 1 in the presence of both 2 and phenol 6 gave dienone 8 additionally. The formation of 24 and 4 was facilitated by conducting the reaction of 1 and 2 in DMSO. Dehydrogenation of 10 and 3 with PbO2 afforded spirodienones 27 and 28, respectively. Compounds 27 and 28 were unstable, and their decay in solution was investigated in the presence or absence of added 2. The results show that the decay is initiated by homolytic scission of the C-C bond connecting the dienone rings in the cyclopentane (in 27) and cyclohexane (in 28) rings. Compound 28 is novel in that it bears two kinds of such C-C bonds. Reversibility of the dimerization of 1 is suggested.