4-<<4-(Diethylamino)phenyl>imino>-2,5-cyclohexadien-1-one | 4704-35-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-<<4-(Diethylamino)phenyl>imino>-2,5-cyclohexadien-1-one
• 英文别名: N-(4-Diethylaminophenyl)-1,4-benzoquinoneimine；Diethylindoaniline；[1,4]benzoquinone-mono-(4-diethylamino-phenylimine)；[1,4]Benzochinon-mono-(4-diaethylamino-phenylimin)；Benzochinon-(1.4)-mono-(4-diaethylamino-anil)；Diaethylindophenol；4-[4-(Diethylamino)phenyl]iminocyclohexa-2,5-dien-1-one
• CAS: 4704-35-2
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: KHLOPSYOSBCQPA-UHFFFAOYSA-N

物化性质

• 熔点：
  104-107 °C
• 沸点：
  388.4±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 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：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  以 aq. phosphate buffer 为溶剂， 生成 4-<<4-(Diethylamino)phenyl>imino>-2,5-cyclohexadien-1-one
  参考文献：
  名称：

  一些二胺衍生物的热力学和电化学氧化：实验和理论研究

  摘要：

  Electrochemical oxidation of some diamine derivatives (1H(+)-411(+)) has been investigated both experimentally and theoretically. Experimental results were obtained using cyclic voltammetry and controlled potential coulometry and the theoretical results were calculated at DFT (B3LYP and BP86) levels of theory and 6-311+G (p,d) basis set. The calculated result indicates that oxidation potential of 1H(+)-4H(+) is directly dependent on the Delta G(tot) and species with more positive oxidation potential (E-pA1) have larger Delta G(tot), values. Also in this paper electrochemical oxidations of N,N-diethyl-p-phenylenediamine (3) were studied in the absence and in the presence of some nucleophiles. Mechanistic study of the electrochemical oxidation of 3 indicates that its electrochemical oxidation proceed in the thermodynamically favored direction. (C) 2015 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.0351512jes

文献信息

• Functional Enhancement of Electrofusion-derived BRIN-BD11 Insulin-secreting Cells After Implantation into Diabetic Mice
  作者：Emma L. Davies、Yasser H. A. Abdel-Wahab、Peter R. Flatt、Clifford J. Bailey

  DOI：10.1155/edr.2001.29

  日期：——

  Electrofusion-derived BRIN-BD11 cells are glucosesensitive insulin-secreting cells which provide an archetypal bioengineered surrogate β-cell for insulin replacement therapy in diabetes mellitus, 5x106BRIN-BD11 cells were implanted intraperitoneally into severely hyperglycaemic (>24mmol/l) streptozotocin-induced insulin-treated diabetic athymic nude (nu/nu) mice. The implants reduced hyperglycaemia such that insulin injections were discontinued by 5–16 days (<17mmol/l) and normoglycaemia (<9mmol/l) was achieved by 7–20 days. Implanted cells were removed after 28 days and re-established in culture. After re-culture for 20 days, glucose-stimulated (16.7mmol/l) insulin release was enhanced by 121% (p<0.001) compared to non-implanted cells. Insulin responses to glucagon-like peptide-1 (10−9mol/l), cholecystokinin-8 (10−8mol/l) and L-alanine (10 mmol/l) were increased by 32%, 31% and 68% respectively (p<0.05–0.01). Insulin content of the cells was 148% greater at 20 days after re-culture than before implantation (p<0.001), but basal insulin release (at 5.6 mmol/l glucose) was not changed. After re-culture for 40 days, insulin content declined to 68% of the content before implantation (p<0.01), although basal insulin release was unchanged. However, the insulin secretory responses to glucose, glucagonlike peptide-1, cholecystokinin-8 and L-alanine were decreased after 40 days of re-culture to 65%, 72%, 73% and 42% respectively of the values before implantation (p<0.05–0.01). The functional enhancement of electrofusion-derived surrogate β-cells that were re-cultured for 20 days after implantation and restoration of normoglycaemia indicates that thein vivoenvironment could greatly assist β-cell engineering approaches to therapy for diabetes.

  将 5x106BRIN-BD11 细胞腹腔植入严重高血糖（24mmol/l）的链脲佐菌素诱导的胰岛素治疗糖尿病裸鼠（nu/nu）。植入细胞降低了高血糖，使小鼠在 5-16 天（<17mmol/l）内停止注射胰岛素，并在 7-20 天内达到正常血糖（<9mmol/l）。植入的细胞在 28 天后被移除，并重新进行培养。重新培养 20 天后，葡萄糖刺激的（16.7 毫摩尔/升）胰岛素释放量比未植入细胞增加了 121%（p<0.001）。胰岛素对胰高血糖素样肽-1（10-9mol/l）、胆囊收缩素-8（10-8mol/l）和L-丙氨酸（10 mmol/l）的反应分别增加了32%、31%和68%（p<0.05-0.01）。重新培养 20 天后，细胞中的胰岛素含量比植入前增加了 148%（p<0.001），但基础胰岛素释放量（5.6 毫摩尔/升葡萄糖）没有变化。再培养 40 天后，胰岛素含量下降到植入前的 68%（p<0.01），但基础胰岛素释放量没有变化。然而，对葡萄糖、胰高血糖素样肽-1、胆囊收缩素-8 和 L-丙氨酸的胰岛素分泌反应在再培养 40 天后分别降至植入前的 65%、72%、73% 和 42%（p<0.05-0.01）。植入后再培养 20 天的电融合衍生代用 β 细胞功能增强，血糖恢复正常，这表明体内环境可以极大地帮助 β 细胞工程方法治疗糖尿病。
• Electrochemical Synthesis and Mechanestic Study of Quinone Imines Exploiting the Dual Character of <i>N,N</i>-Dialkyl-<i>p</i>-phenylenediamines
  作者：Abbas Maleki、Davood Nematollahi

  DOI：10.1021/ol103146k

  日期：2011.4.15

  Two one-pot electrochemical approaches for the synthesis of similar quinone imines via either the nucleophilic character of N,N-dialkyl-p-phenylenediamines or electrophilic reactivity of their oxidized forms through Michael-type addition reactions are reported.

  报道了两种通过一锅法通过N，N-二烷基-对苯二胺的亲核特性或其通过迈克尔型加成反应氧化形式的亲电反应性来合成相似的醌亚胺的方法。
• The relationship between the structures and absorption spectra of cyan color indoaniline dyes
  作者：Masafumi Adachi、Yukichi Murata、Shinichiro Nakamura

  DOI：10.1021/jo00071a038

  日期：1993.9

  The absorption spectra of 23 indoaniline dyes were calculated on the AM1-optimized structures by means of the INDO/S method. The observed and calculated absorption wavelengths showed good correlation for the main (longest wavelength) absorption bands (observed at 560-670 nm), and there was fair correlation between the observed molar extinction coefficients and the calculated oscillator strengths. The observed absorption wavelengths could be reproduced by the calculation for the subabsorption bands near the visible region (observed at 320-380 nm). A qualitative correlation of the solvatochromic shift with the difference between ground and excited state dipole moments was obtained.
• Fundamental Studies on the Structure and Spectroscopic Behavior of Phenol Blue
  作者：John O. Morley、Ann L. Fitton

  DOI：10.1021/jp992610v

  日期：1999.12.1

  The structure and spectroscopic properties of Phenol Blue [N-(4-dimethylaminophenyl)- 1,4-benzoquinoneimine (4)], which can exist in principle either as a zwitterion (A) or as a quinoneimine (B), have been assessed both experimentally and theoretically using molecular orbital methods. C-13 NMR evidence on the more soluble diethylamino derivative (6) strongly suggests that the molecule exists purely as the quinoneimine (B) both in protic solvents and in aprotic solvents of low and high dielectric constant. Theoretically, the solvatochromic shift of the dye in aprotic solvents, calculated using the PM3/COSMO method, shows a good correlation with the experimental data and arises because solvents with large dielectric constants exert a much greater stabilizing influence on the more polar excited state than they do on the ground state. In protic solvents, the larger bathochromic shifts observed are attributable to both a dielectric effect and a separate hydrogen bonding contribution from the solvent. In water, Phenol Blue is predicted to form a stable trihydrate which is calculated at the CNDOVS level of theory to absorb at a significantly longer wavelength than the unsolvated structure in line with the experimental data.