4,4'-Bis-diaethylamino-azobenzol | 3588-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4,4'-Bis-diaethylamino-azobenzol
• 英文别名: tetra-N-ethyl-4,4'-azo-di-aniline；Tetra-N-aethyl-4,4'-azo-di-anilin；Bis-(4-diaethylamino-phenyl)-diazen；p.p'-Azodiaethylanilin；(N.N-Diaethyl-anilin)-(4 azo 4)-(N.N-diaethyl-anilin)；4,4'-Bis-diathylamino-azobenzol；4-[[4-(diethylamino)phenyl]diazenyl]-N,N-diethylaniline
• CAS: 3588-91-8
• 化学式: C₂₀H₂₈N₄
• 分子量: 324.469
• InChiKey: ULWJZUJIVQSWSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2927000090

反应信息

• 作为反应物：
  描述：

  4,4'-Bis-diaethylamino-azobenzol 在 hydrochloride of tin dichloride 作用下， 生成 N,N-二乙基对苯二胺
  参考文献：
  名称：

  Lippmann; Fleissner, Monatshefte fur Chemie, 1883, vol. 4, p. 297

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二乙基对苯二胺 在 CotA laccase 作用下， 以 aq. phosphate buffer 、 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到4,4'-Bis-diaethylamino-azobenzol
  参考文献：
  名称：

  CotA漆酶介导的偶氮苯染料的合成

  摘要：

  据报道，通过伯芳香胺的氧化偶联合成偶氮苯染料的环保方案。作为有效的生物催化系统，CotA漆酶和CotA漆酶/ ABTS（2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸））能够在水性介质，环境气氛中和温和的反应条件下氧化各种取代的苯胺。 pH和温度。在单锅反应中，制备了一系列偶氮苯染料，其收率好至极好。提出了形成偶氮衍生物的机制建议。我们的策略为直接合成偶氮苯染料提供了另一种方法，从而避免了大多数传统合成方法通常需要的苛刻条件。

  DOI：

  10.1002/asia.201801450

文献信息

• Chemoselective Reductive Coupling of Nitroarenes with Magnesium in Methanol via Single Electron Transfer
  作者：Jitender M. Khurana、Abhijit Ray

  DOI：10.1246/bcsj.69.407

  日期：1996.2

  A chemoselective reductive coupling of nitroarenes using magnesium in methanol has been reported at ambient temperature. While the cyano, formyl, methoxycarbonyl, methyl, methoxy, phenyl, amino, and chloro groups are unaffected, iodo and bromo groups undergo dehalogenation but in a slower reaction than the coupling of nitro group. The coupling is believed to be proceeding via SET from Mg to nitroarenes

  已经报道了在环境温度下使用甲醇中的镁进行硝基芳烃的化学选择性还原偶联。虽然氰基、甲酰基、甲氧基羰基、甲基、甲氧基、苯基、氨基和氯基团不受影响，但碘基和溴基团进行脱卤，但反应比硝基偶联慢。据信偶联是通过 SET 从 Mg 进行到硝基芳烃的。
• 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。
• Unprecedented intermolecular aldol-type condensation involving CH-acid and the nitro group
  作者：N. V. Moskalev、M. I. Tartynova

  DOI：10.1007/bf02495619

  日期：1998.8

  The first evidence that α-acylnitrone is an intermediate in the base-promoted reaction of 4-nitro-N,N-diethylaniline with aceptophenome to give an enaminoketone was obtained.

  获得了第一个证据，证明 α-酰基硝酮是 4-硝基-N,N-二乙基苯胺与受体表型反应生成烯氨基酮的碱促进反应的中间体。
• Gold(I)-Catalyzed Oxidative 1,4-Additions of 3-En-1-ynamide with Nitrones via Carbon- versus Nitrogen-Addition Chemoselectivity
  作者：Sudhakar Dattatray Tanpure、Balaji S. Kale、Rai-Shung Liu

  DOI：10.1021/acs.orglett.1c00055

  日期：2021.2.19
• Jorgensen, K. A.; Shabana, R.; Scheibye, S., Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 3, p. 247 - 254
  作者：Jorgensen, K. A.、Shabana, R.、Scheibye, S.、Lawesson, S.-O.

  DOI：——

  日期：——