dimethyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate | 1968-73-6

• 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: dimethyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate
• 英文别名: 2,2a(2)-Dimethyl 3,3a(2),4,4a(2),5,5a(2)-hexamethoxy[1,1a(2)-biphenyl]-2,2a(2)-dicarboxylate；methyl 2,3,4-trimethoxy-6-(3,4,5-trimethoxy-2-methoxycarbonylphenyl)benzoate
• CAS: 1968-73-6
• 化学式: C₂₂H₂₆O₁₀
• 分子量: 450.442
• InChiKey: JXJAAMPHYUDMGS-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  576.1±50.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  dimethyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 dibutyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate
  参考文献：
  名称：

  On the synthesis of a phenanthrene-2,7-quinone

  摘要：

  Oxidative coupling of 2,2',4,4'-tetramethoxystilbene-3,3'-diol 51 gave a 51% yield of 1,3,6,8-tetramethoxyphenanthrene-2,7-quinone 52, the first isolated example of a quinone of this type. Similar oxidation of the corresponding diphenylethane 55 gave the 9,10-dihydrophenanthrene-2,7-quinone 56. Attempts to synthesize the tetramethoxyphenanthrene-2,7-diol 25 from a 2,2'-bis(hydroxymethyl)hexamethoxybiphenyl precursor 28 were thwarted by the ease of intramolecular cyclization to 2,3,4,8,9,10-hexamethoxydibenz[c,e]oxepine 32. Selective demethylation of the 3- and 9-methoxy groups of this compound, and oxidation of the resulting diol 58 gave the dibenzoxepine quinone 59.The synthesis of 3,6-di-tert-butylphenanthrene-2,7-diol 3 is also described, but this could not be oxidized to the quinone. However, the preparation of 3,6-di-tert-butyl-9,10-dihydrophenanthrene-2,7-quinone 12 was successful.

  DOI：

  10.1039/p19910003033
• 作为产物：
  描述：

  methyl 6-amino-2,3,4-trimethoxybenzoate 在 盐酸 、 铜 、 potassium iodide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.75h， 生成 dimethyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate
  参考文献：
  名称：

  On the synthesis of a phenanthrene-2,7-quinone

  摘要：

  Oxidative coupling of 2,2',4,4'-tetramethoxystilbene-3,3'-diol 51 gave a 51% yield of 1,3,6,8-tetramethoxyphenanthrene-2,7-quinone 52, the first isolated example of a quinone of this type. Similar oxidation of the corresponding diphenylethane 55 gave the 9,10-dihydrophenanthrene-2,7-quinone 56. Attempts to synthesize the tetramethoxyphenanthrene-2,7-diol 25 from a 2,2'-bis(hydroxymethyl)hexamethoxybiphenyl precursor 28 were thwarted by the ease of intramolecular cyclization to 2,3,4,8,9,10-hexamethoxydibenz[c,e]oxepine 32. Selective demethylation of the 3- and 9-methoxy groups of this compound, and oxidation of the resulting diol 58 gave the dibenzoxepine quinone 59.The synthesis of 3,6-di-tert-butylphenanthrene-2,7-diol 3 is also described, but this could not be oxidized to the quinone. However, the preparation of 3,6-di-tert-butyl-9,10-dihydrophenanthrene-2,7-quinone 12 was successful.

  DOI：

  10.1039/p19910003033

文献信息

• 2,2′-Biaryldicarboxylate Synthesis via Electrocatalytic Dehydrogenative C–H/C–H Coupling of Benzoic Acids
  作者：Zhongyi Zeng、Jonas F. Goebel、Xianming Liu、Lukas J. Gooßen

  DOI：10.1021/acscatal.1c01127

  日期：2021.6.4

  catalysts. These compounds have been found to be conveniently accessible from benzoic acids via Rh-catalyzed electrooxidative C–H/C–H couplings, giving valuable dihydrogen as the byproduct. In an undivided cell with Pt electrodes, RhCl3·3H2O catalyzes the oxidative carboxylate-directed ortho-homocoupling of various aromatic acids with a current efficiency of 67%. The protocol is operationally simple, tolerates

  2,2'-二芳基二羧酸酯是生物活性化合物、功能材料和手性催化剂中的重要功能。已经发现这些化合物可以通过 Rh 催化的电氧化 C-H/C-H 偶联从苯甲酸中方便地获得，并提供有价值的二氢作为副产物。在带有 Pt 电极的未分割电池中，RhCl 3 ·3H 2 O以 67% 的电流效率催化各种芳香酸的氧化羧酸定向邻位均偶联。该协议操作简单，可以容忍多种功能组，并且不需要排除空气和水分。通过萘基-1-羧酸与丙烯酸或苯甲酸的交叉脱氢偶联的异二聚化也被证明是有效的。
• Bowden, Bruce F.; Read, Roger W.; Taylor, Walter C., Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 799 - 817
  作者：Bowden, Bruce F.、Read, Roger W.、Taylor, Walter C.

  DOI：——

  日期：——
• On the synthesis of a phenanthrene-2,7-quinone
  作者：Frank R. Hewgill、Riskiono Slamet、Jeffery M. Stewart

  DOI：10.1039/p19910003033

  日期：——

  Oxidative coupling of 2,2',4,4'-tetramethoxystilbene-3,3'-diol 51 gave a 51% yield of 1,3,6,8-tetramethoxyphenanthrene-2,7-quinone 52, the first isolated example of a quinone of this type. Similar oxidation of the corresponding diphenylethane 55 gave the 9,10-dihydrophenanthrene-2,7-quinone 56. Attempts to synthesize the tetramethoxyphenanthrene-2,7-diol 25 from a 2,2'-bis(hydroxymethyl)hexamethoxybiphenyl precursor 28 were thwarted by the ease of intramolecular cyclization to 2,3,4,8,9,10-hexamethoxydibenz[c,e]oxepine 32. Selective demethylation of the 3- and 9-methoxy groups of this compound, and oxidation of the resulting diol 58 gave the dibenzoxepine quinone 59.The synthesis of 3,6-di-tert-butylphenanthrene-2,7-diol 3 is also described, but this could not be oxidized to the quinone. However, the preparation of 3,6-di-tert-butyl-9,10-dihydrophenanthrene-2,7-quinone 12 was successful.