meso-1,2-bis(4-dimethylaminophenyl)-1,2-ethanediol | 86001-22-1

• 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: meso-1,2-bis(4-dimethylaminophenyl)-1,2-ethanediol
• 英文别名: 1,2-bis[4-(dimethylamino)phenyl]-1,2-ethanediol；meso-4,4'-bis-dimethylamino-bibenzyl-α,α'-diol；(1R,2S)-1,2-bis[4-(dimethylamino)phenyl]ethane-1,2-diol
• CAS: 86001-22-1
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: RHYWTTJMPMTONP-HDICACEKSA-N

物化性质

• 沸点：
  491.3±45.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  meso-1,2-bis(4-dimethylaminophenyl)-1,2-ethanediol 以 氯仿 为溶剂， 反应 2.0h， 以78%的产率得到对二甲氨基苯甲醛
  参考文献：
  名称：

  Zhang, Wei; Yang, Li; Wu, Long-Min, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 5, p. 1189 - 1193

  摘要：

  DOI：
• 作为产物：
  描述：

  对二甲氨基苯甲醛 在 甲醇 、 氢氧化钾 、 氢化铝 作用下， 反应 0.08h， 以87%的产率得到meso-1,2-bis(4-dimethylaminophenyl)-1,2-ethanediol
  参考文献：
  名称：

  Pinacolization and reduction of aromatic carbonyls with aluminium–KOH

  摘要：

  A simple and rapid procedure for the pinacolization of aromatic aldehydes and reduction of hindered ketones with inexpensive aluminium and KOH in methanol at ambient temperature is reported, The pinacolization and reduction are proposed to be proceeding via single electron transfer from aluminium.

  DOI：

  10.1039/p19960002213

文献信息

• Preparation, Crystal Structures, and Properties of New Conjugated π-Electron Systems with 3-Guaiazulenyl and 4-(Dimethylamino)phenyl Groups
  作者：Shin-ichi Takekuma、Seiki Hori、Toshie Minematsu、Hideko Takekuma

  DOI：10.1246/bcsj.81.1472

  日期：2008.11.15

  Reaction of guaiazulene with 1,2-bis[4-(dimethylamino)phenyl]-1,2-ethanediol in methanol in the presence of hydrochloric acid at 60 °C for 3 h gives 1,1-bis[4-(dimethylamino)phenyl]-2-(3-guaiazulen...

  愈创甘油醚与 1,2-双[4-(二甲氨基)苯基]-1,2-乙二醇在甲醇中在盐酸存在下于 60 °C 反应 3 小时，得到 1,1-双[4-(二甲氨基)苯基]-2-(3-愈创木酚...
• A Study of the Reduction Mechanism of<i>p</i>-Dimethylaminobenzaldehyde to 1,2-Bis(<i>p</i>-dimethylaminophenyl)-1,2-ethanediol by Rotating Disk Electrode Voltammetry
  作者：Isao Taniguchi、Kazuo Yasukouchi、Akiko Yoshiyama、Taro Sekine

  DOI：10.1246/bcsj.52.1775

  日期：1979.6

  Rotating disk electrode voltammetry was applied to study the reduction mechanism of p-dimethylaminobenzaldehyde (1) in water–ethanol alkaline solutions by using a mercury-plated platinum rotating disk electrode. In the logarithmic analysis of the wave, the plots of log [i2⁄3/(id–i)] vs.  E showed good linearity, and the shifts of the half-wave potential with an increase in the rotation speed of the electrode (ω) and in the initial concentration of 1 (C) were ∂E1⁄2⁄∂logω=−22±2 mV and ∂E1⁄2⁄∂logC=19±2 mV, respectively. On the other hand, no appreciable change in E1⁄2 was observed with varying alkalinities of the solutions. These results and the large shift of E1⁄2 with an increase in the concentration of water (∂E1⁄2⁄∂log[H2O]=ca. 50 mV) are explained in terms of the following reactions:R+e\ightleftarrowsR\ewdot (solvated by water), (1)2R\ewdot\oversetk→D2− (r.d.s.), (2)D2−+2H2O→DH2+2OH−, (3)where R and R\ewdot are the molecule and the radical of 1, respectively, D2− is the dimer of R\ewdot and DH2 is the hydro-dimer (2) of R. The rate of the dimerization reaction (k in Eq. 2) was estimated to be 2.5×104 M−1 s−1 from the shift of E1⁄2 with logω for the 50% water-ethanol solution containing 1 M NaOH, and this rate constant decreased with decreasing water concentration.

  利用镀汞铂旋转盘电极，采用旋转盘电极伏安法研究了对二甲氨基苯甲醛（1）在水乙醇碱性溶液中的还原机理。在波的对数分析中，对数[i2⁄3/(id-i)]与E的关系图显示出良好的线性，半波电位随电极旋转速度（ω）和1的初始浓度（C）的增加而移动，分别为∂E1⁄2⁄∂ωlogC=-22±2 mV和∂E1⁄2⁄∂logC=19±2 mV。另一方面，随着溶液碱度的变化，E1⁄2 没有明显变化。这些结果以及 E1⁄2 随着水浓度的增加而发生的巨大变化（∂E1⁄2⁄∂log[H2O]=约 50 mV）可以用以下反应来解释：R+e（被水溶解），(1)2R\ewdot\oversetk→D2-（r.d.s.(2)D2-+2H2O→DH2+2OH-, (3)where R and R\ewdot are the molecule and the radical of 1, D2- is the dimer of R\ewdot and DH2 is the hydro-dimer (2) of R. The rate of the dimerization reaction (k in Eq. 2) was estimated to be 2.5 per cent.根据含有 1 M NaOH 的 50% 水-乙醇溶液中 E1⁄2 随 logω 的移动，估计二聚化反应的速率（式 2 中的 k）为 2.5×104 M-1 s-1，且该速率常数随水浓度的降低而减小。
• Fuerstner, Alois; Csuk, Rene; Rohrer, Christian, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1729 - 1734
  作者：Fuerstner, Alois、Csuk, Rene、Rohrer, Christian、Weidmann, Hans

  DOI：——

  日期：——
• Photochemical Electron Transfer Initiated Oxidative Fragmentation of Aminopinacols. Factors Governing Reaction Rates and Quantum Efficiencies of C-C Bond Cleavage
  作者：Hong Gan、Uwe Leinhos、Ian R. Gould、David G. Whitten

  DOI：10.1021/j100011a025

  日期：1995.3

  The fragmentation reactions of the cation radicals of a series of remote diamine-substituted pinacols have been investigated. The cation radicals were generated upon photooxidation with excited 2,6,9,10-tetracyanoanthracene in acetonitrile. The products are consistent with cleavage of the central C-C bond. The rate constants for fragmentation were determined both from steady-state quantum yield studies and from time-resolved measurements. In general, the rate constants for fragmentation increase with increasing stability of the radical and cation products. However, the results of temperature dependence studies clearly demonstrate that conformational effects play an important role in the transition state. In some cases, these conformational effects can result in changes in the reactivity order expected from purely thermodynamic considerations.
• THE PREPARATION OF SOME SUBSTITUTED GLYCOLS BY ELECTROLYTIC REDUCTION
  作者：MILTON J. ALLEN

  DOI：10.1021/jo01148a032

  日期：1950.3