2,2'-(2-methyl-1,4-phenylenedioxy)diethanol | 116943-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2'-(2-methyl-1,4-phenylenedioxy)diethanol
• 英文别名: 1,4-Bis(2-hydroxyethoxy)-2-methylbenzol；2-[4-(2-Hydroxyethoxy)-3-methylphenoxy]ethanol
• CAS: 116943-38-5
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: CUCKFLUMSJLSHH-UHFFFAOYSA-N

物化性质

• 沸点：
  390.7±32.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-(2-methyl-1,4-phenylenedioxy)diethanol 在 四氯化锡 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 2,5-Bis(2-chlorethoxy)-4-methylbenzaldehyd
  参考文献：
  名称：

  2,5-Dialkoxysubstituierte Oligo- und Poly(1,4-phenylenethenylen)e

  摘要：

  O-Alkylation and regioselective Rieche formylation of 2-methylhydroquinone (1) yields the 2,5-dialkoxy-4-methylbenzaldehydes 4a-j. The corresponding azomethines 5a-j enter in a strongly alkaline medium a self-condensation reaction leading to the title compounds 6/7a-j. These conjugated oligomers and polymers possess highly regular structures with exclusively (E)-configurated double bonds. GPC, IR, H-1-, C-13-NMR and MS-FD measurements were used for their characterization. Somewhat different results were obtained for the similarly prepared Schiff base 51 which contains chlorine substituents in the side chains. Cleavage of hydrogen chloride leads not only to unsaturated alkoxy groups; additionally, cyclization reactions (51 --> 81) are observed.

  DOI：

  10.1002/prac.19943360311
• 作为产物：
  描述：

  甲基氢醌 、 2-氯乙醇 在 氢氧化钾 、 甲基三辛基氯化铵 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以25%的产率得到2,2'-(2-methyl-1,4-phenylenedioxy)diethanol
  参考文献：
  名称：

  2,5-Dialkoxysubstituierte Oligo- und Poly(1,4-phenylenethenylen)e

  摘要：

  O-Alkylation and regioselective Rieche formylation of 2-methylhydroquinone (1) yields the 2,5-dialkoxy-4-methylbenzaldehydes 4a-j. The corresponding azomethines 5a-j enter in a strongly alkaline medium a self-condensation reaction leading to the title compounds 6/7a-j. These conjugated oligomers and polymers possess highly regular structures with exclusively (E)-configurated double bonds. GPC, IR, H-1-, C-13-NMR and MS-FD measurements were used for their characterization. Somewhat different results were obtained for the similarly prepared Schiff base 51 which contains chlorine substituents in the side chains. Cleavage of hydrogen chloride leads not only to unsaturated alkoxy groups; additionally, cyclization reactions (51 --> 81) are observed.

  DOI：

  10.1002/prac.19943360311

文献信息

• Photochemical rearrangements of quinone monoketals
  作者：Michael C. Pirrung、David S. Nunn

  DOI：10.1016/0040-4020(96)00207-4

  日期：1996.4

  provides, after hydrolysis, β-carboxy-substituted cyclopentenones. With a substituent at the β-position of the quinone monoketal, rearrangement selectivity is modestly in favor of the more substituted alkene product. With a substituent at the α-position of the quinone monoketal, rearrangement selectivity is strongly in favor of the less substituted alkene product. Possible mechanistic reasoning to explain

  我们已经研究了15种以上的醌环单缩酮的光化学，这些缩酮是通过二甲基缩酮的二醇交换，Swenton氧化/水解或直接缩酮化制备的。它们在酸性介质中的反应通常通过环己二烯酮光化学（di-π-甲烷）重排的经典机理来解释：将光环化为质子化的环丙烷-氧化烯丙基化，然后进行溶剂分解。该反应路径在水解后提供β-羧基取代的环戊烯酮。在醌单缩酮的β-位具有取代基时，适度的重排选择性有利于更多取代的烯烃产物。在醌单缩酮的α-位上具有取代基的情况下，重排选择性强烈倾向于较少取代的烯烃产物。
• Photochemical rearrangements of quinone monoketals. Synthesis of substituted cyclopentenones
  作者：Michael C. Pirrung、David S. Nunn

  DOI：10.1016/s0040-4039(00)80042-8

  日期：1988.1

  The irradiation of quinone ethylene monoketals in acetic acid leads in high yield to substituted 4-(alkoxycarbonyl) cyclopentenones.

  苯醌乙烯单缩酮在乙酸中的照射导致高产率生成取代的4-（烷氧羰基）环戊烯酮。
• PIRRUNG, MICHAEL C.;NUNN, DAVID S., TETRAHEDRON LETT., 29,(1988) N 2, 163-166
  作者：PIRRUNG, MICHAEL C.、NUNN, DAVID S.

  DOI：——

  日期：——
• 2,5-Dialkoxysubstituierte Oligo- und Poly(1,4-phenylenethenylen)e
  作者：H. Kretzschmann、H. Meier

  DOI：10.1002/prac.19943360311

  日期：——

  O-Alkylation and regioselective Rieche formylation of 2-methylhydroquinone (1) yields the 2,5-dialkoxy-4-methylbenzaldehydes 4a-j. The corresponding azomethines 5a-j enter in a strongly alkaline medium a self-condensation reaction leading to the title compounds 6/7a-j. These conjugated oligomers and polymers possess highly regular structures with exclusively (E)-configurated double bonds. GPC, IR, H-1-, C-13-NMR and MS-FD measurements were used for their characterization. Somewhat different results were obtained for the similarly prepared Schiff base 51 which contains chlorine substituents in the side chains. Cleavage of hydrogen chloride leads not only to unsaturated alkoxy groups; additionally, cyclization reactions (51 --> 81) are observed.