1,1,2,2-tetrakis<4-(dimethylamino)phenyl>-1,2-ethanediol | 19422-49-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1,2,2-tetrakis<4-(dimethylamino)phenyl>-1,2-ethanediol
• 英文别名: tetra-p-dimethylaminophenyl ethylene glycol；4,4',4'',4'''-Tetra-(dimethylamino)-benzpinakol；Michler's Pinakol；Tetrakis-<4-dimethylamino-phenyl>-aethylenglykol；Tetrakis-(4-dimethylamino-phenyl)-aethan-1,2-diol；tetrakis-(4-dimethylamino-phenyl)-ethane-1,2-diol；4.4'.4''.4'''-Tetrakis-dimethylamino-benzpinakon；Tetrakis-(4-dimethylamino-phenyl)-aethylenglykol；Oktamethyl-p-tetraamino-benzpinakon；1,1,2,2-Tetrakis[4-(dimethylamino)phenyl]ethane-1,2-diol
• CAS: 19422-49-2
• 化学式: C₃₄H₄₂N₄O₂
• 分子量: 538.733
• InChiKey: KOWPYMYAFBMLIF-UHFFFAOYSA-N

物化性质

• 沸点：
  694.2±55.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1,2,2-tetrakis<4-(dimethylamino)phenyl>-1,2-ethanediol 在 potassium superoxide 、 四乙基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以56%的产率得到米氏酮
  参考文献：
  名称：

  Singh, Krishna Nand; Kumar, Rajesh; Shukla, Ajay Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 8, p. 1347 - 1351

  摘要：

  DOI：
• 作为产物：
  描述：

  米氏酮 在 aluminium amalgam 作用下， 以 乙醇 为溶剂， 生成 1,1,2,2-tetrakis<4-(dimethylamino)phenyl>-1,2-ethanediol
  参考文献：
  名称：

  1,2-二取代的四芳基乙烷中脂族碳-碳键的旋转受限

  摘要：

  先前报道的1,2-二氯四苯乙烷稳定的旋转异构体的存在被证明是不正确的，因为偶极矩测量表明仅存在反式。大量的1,2-二取代的四芳基乙烷的红外研究无法解释可能的薄纱形式的存在，只有在这种构型中出现的乙烷1,2-二醇除外。

  DOI：

  10.1039/j39680000696

文献信息

• Radical cation catalyzed pinacol-pinacolone rearrangement
  作者：J.Arce de Sanabia、Arturo E. Carrión

  DOI：10.1016/s0040-4039(00)61489-2

  日期：1993.12

  When electron-rich benzopinacols are electrooxidized or treated with catalytic amounts of NOBF4 the corresponding pinacolones are obtained in quantitative yields. Control experiments rule out the possibility of adventitious acid intervening in the reaction and a radical-cation chain electron-transfer mechanism is proposed.

  当富电子的苯并频哪醇被电氧化或用催化量的NOBF 4处理时，可以定量产率获得相应的频哪醇。控制实验排除了不定酸介入反应的可能性，并提出了自由基-阳离子链电子转移机理。
• Wizinger, Chemische Berichte, 1927, vol. 60, p. 1386
  作者：Wizinger

  DOI：——

  日期：——
• Madelung; Oberwegner, Chemische Berichte, 1927, vol. 60, p. 2484
  作者：Madelung、Oberwegner

  DOI：——

  日期：——
• Cohen, Recueil des Travaux Chimiques des Pays-Bas, 1919, vol. 38, p. 121
  作者：Cohen

  DOI：——

  日期：——
• Reactions of Pinacols with One-Electron Oxidants
  作者：Dong Sul Han、Henry J. Shine

  DOI：10.1021/jo952217v

  日期：1996.1.1

  Oxidation of the tetraarylpinacols (Ar2COH)(2), 1a-e, in which Ar = C6H5 (1a), 4-ClC6H4 (1b), 4-MeC(6)H(4) (1c), 4-MeOC(6)H(4) (1d) and 4-Me(2)NC(6)H(4) (1e), by thianthrene cation radical (Th-.+) in CH3CN and in CH2Cl2 led quantitatively to the corresponding diaryl ketones Ar2C = O (2a-e), provided a sufficient amount of base, 2,6-di-tert-butyl-4-methylpyridine (DTBMP), was present to prevent presumed acid-catalyzed rearrangement. In the case of 1e, continued oxidation of 2e was also observed. Oxidation of 1a by (4-BrC6H4)(3)(NSbCl6-)-Sb-.+ and (4-BrC6H4)(3)(NSbF6-)-Sb-.+ (Ar3N.+) occurred analogously. Evidence for the catalytic, cation-radical rearrangement of 1a by Ar3N.+ (reported in earlier literature) and by Th-.+ could not be found. Quantitative oxidation of 1a to 2a and of 1d to 2d was obtained also with NOBF4, again provided that sufficient DTBMP was present to prevent acid-catalyzed rearrangement. Catalytic, oxidative rearrangement of Id at room temperature and (as reported in earlier literature) at -5 degrees C was not observed. Oxidation was also observed of 2,3-diphenyl-2,3-butanediol (3) to acetophenone (9) and of 1,1-dimethyl-2,2-diphenylethanediol (4) to 2a and acetone by Th-.+. Oxidation of 2,3-dimethyl-2,3-butanediol (5) by Th-.+ was not observed. Instead, even in the presence of DTBMP, pinacolone (10) and tetramethyloxirane (11) were formed, through, it is proposed, a mechanism involving complexation with Th-.+.