Leuco Bindschedler's Green

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Leuco Bindschedler's Green
• 英文别名: N,N-bis(p-dimethylaminophenyl)amine hydrochloride；Bis(4-dimethylaminophenyl)amine hydrochloride；1-N-[4-(dimethylamino)phenyl]-4-N,4-N-dimethylbenzene-1,4-diamine;hydrochloride
• 化学式: C₁₆H₂₁N₃*ClH
• 分子量: 291.824
• InChiKey: ZAHVATMSLRZLLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.65
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  杜醌 、 Leuco Bindschedler's Green 以 丙酮 为溶剂， 生成 彬氏绿
  参考文献：
  名称：

  Reactions of Leuco Bindschedler’s Green with Somep-Benzoquinones in Acetone

  摘要：

  通过停流技术，对 Leuco Bindschedler's Green（BGH）和一些对苯醌衍生物（Q's）在丙酮中的反应速率进行了分光光度法测定。结果发现反应是可逆进行的。估算了正向和逆向反应的速率数据和活化参数。速率易受 Q 的氧化还原电位的影响。在低温下观察到的吸收光谱表明，其中涉及三种中间产物。通过 ESR 方法检测了反应过程中形成的自由基。讨论的结果与之前在涉及褐晶紫（LCV）和褐孔雀石绿（LMG）的体系中获得的结果有关。

  DOI：

  10.1246/bcsj.64.2648
• 作为产物：
  描述：

  N,N-bis(p-dimethylaminophenyl)benzamide 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以94%的产率得到Leuco Bindschedler's Green
  参考文献：
  名称：

  Practical Synthesis of Aromatic Dithiocarbamates

  摘要：

  Oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) are synthesized in good yields by the generation of metal amide salts from N-benzoyl precursors, followed by addition of CS₂. para-Substituted diphenylamines are prepared by electrophilic aromatic substitution of diphenylbenzamide and saponification. Deacylation of electron-rich species such as bis(p-dimethylaminophenyl)benzamide is challenging because of the oxidative sensitivity of the anionic intermediate but could be achieved in good yield by using n-BuLi to generate a hemiaminal adduct, prior to acidification. The N,N-diaryl DTCs are stable as alkali salts and can be used to produce densely packed monolayers on gold surfaces.

  DOI：

  10.1080/00397911.2014.894527

文献信息

• Practical Synthesis of Aromatic Dithiocarbamates
  作者：Panuwat Padungros、Alexander Wei

  DOI：10.1080/00397911.2014.894527

  日期：2014.8.18

  Oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) are synthesized in good yields by the generation of metal amide salts from N-benzoyl precursors, followed by addition of CS₂. para-Substituted diphenylamines are prepared by electrophilic aromatic substitution of diphenylbenzamide and saponification. Deacylation of electron-rich species such as bis(p-dimethylaminophenyl)benzamide is challenging because of the oxidative sensitivity of the anionic intermediate but could be achieved in good yield by using n-BuLi to generate a hemiaminal adduct, prior to acidification. The N,N-diaryl DTCs are stable as alkali salts and can be used to produce densely packed monolayers on gold surfaces.
• Reactions of Leuco Bindschedler’s Green with Some<i>p</i>-Benzoquinones in Acetone
  作者：Yoshihiro Osawa、Norio Nishimura、Shunzo Yamamoto

  DOI：10.1246/bcsj.64.2648

  日期：1991.9

  The rate of reaction between Leuco Bindschedler’s Green (BGH) and some p-benzoquinone derivatives (Q’s) in acetone was followed spectrophotometrically by means of the stopped-flow technique. The reaction was found to proceed reversibly. The rate data and the activation parameters for the forward and backward reactions were estimated. The rates were susceptible to the oxidation–reduction potentials of the Q’s. The absorption spectra observed at low temperatures indicated that three kinds of intermediates were involved. Radicals formed during the reaction were detected by the ESR method. The results have been discussed in relation to those previously obtained for systems involving Leuco Crystal Violet (LCV) and Leuco Malachite Green (LMG).

  通过停流技术，对 Leuco Bindschedler's Green（BGH）和一些对苯醌衍生物（Q's）在丙酮中的反应速率进行了分光光度法测定。结果发现反应是可逆进行的。估算了正向和逆向反应的速率数据和活化参数。速率易受 Q 的氧化还原电位的影响。在低温下观察到的吸收光谱表明，其中涉及三种中间产物。通过 ESR 方法检测了反应过程中形成的自由基。讨论的结果与之前在涉及褐晶紫（LCV）和褐孔雀石绿（LMG）的体系中获得的结果有关。