4-甲基氨基苯甲醛 | 556-21-8

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲基氨基苯甲醛
• 英文名称: 4-(methylamino)benzaldehyde
• 英文别名: 4-N-(methylamino)benzaldehyde；p-methylaminobenzenecarboxaldehyde
• CAS: 556-21-8
• 化学式: C₈H₉NO
• mdl: MFCD19105577
• 分子量: 135.166
• InChiKey: ZRKUQAXOMUSPEH-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  185-187 °C(Press: 15 Torr)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090
• 储存条件：
  应存放在2-8°C的环境中，避免光照，并在惰性气体保护下保存。

反应信息

• 作为反应物：
  描述：

  4-甲基氨基苯甲醛 在 哌啶 、 甲醇 、 magnesium 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 5-[4-(methylamino)benzyl]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Design and Synthesis of the First Generation of Dithiolane Thiazolidinedione- and Phenylacetic Acid-Based PPARγ Agonists

  摘要：

  A series of novel derivatives of potent antioxidant vitamin, alpha-lipoic acid, and related analogues were designed, synthesized, and evaluated for their PPAR gamma agonist activities. Compounds 9a and the water soluble analogue 11e were found to be potent PPAR gamma agonists. Compound 9a appeared to have a significant role in improving insulin sensitivity and reducing triglyceride levels in fa/fa rats as well as inhibited proliferation of a variety of normal and neoplastic cultured human cell types. These novel compounds may prove efficacious not only in the treatment of Type 2 diabetes, but also atherosclerosis, prevention of vascular restenosis, and inflammatory skin diseases.

  DOI：

  10.1021/jm0510880
• 作为产物：
  描述：

  [4-(甲基氨基)苯基]甲醇 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以47%的产率得到4-甲基氨基苯甲醛
  参考文献：
  名称：

  A Reversible Reaction Inside a Self-Assembled Capsule

  摘要：

  Reversible encapsulation allows the direct observation of the isolated molecules under ambient conditions, at equilibrium and in the liquid phase. Here we show that capsules can amplify and stabilize molecules that are present in only trace concentrations in solution. Evidence is given that reversible chemical reactions take place within the capsule. Stabilization of reaction intermediates is a characteristic property of enzymes and is widely regarded as an essential feature of catalytic activity. Reactive molecules can also be stabilized by encapsulation, a process that involves completely surrounding the reactive species within synthetic receptors. Here, we show that self-assembled capsules can isolate and stabilize molecules that are present in only trace amounts in solution. The system amplifies the concentrations of high-energy species with reduced entropies.

  DOI：

  10.1021/ja062768a

文献信息

• Copper Bis(thiosemicarbazonato)-stilbenyl Complexes That Bind to Amyloid-β Plaques
  作者：Asif Noor、David J. Hayne、SinChun Lim、Jessica K. Van Zuylekom、Carleen Cullinane、Peter D. Roselt、Catriona A. McLean、Jonathan M. White、Paul S. Donnelly

  DOI：10.1021/acs.inorgchem.0c01520

  日期：2020.8.17

  copper-64 radionuclides that bind to amyloid-β plaques, a family of bis(thiosemicarbazone) ligands with appended substituted stilbenyl functional groups has been prepared. The ligands form charge-neutral and stable complexes with copper(II). The new ligands can be radiolabeled with copper-64 at room temperature. Two lead complexes were demonstrated to bind to amyloid-β plaques present in post-mortem

  阿尔茨海默氏病的特征在于存在细胞外淀粉样蛋白-β斑块。用示踪剂进行正电子发射断层扫描（PET）成像，该示踪剂用与β-淀粉样蛋白斑块结合的正电子发射放射性核素进行放射性标记，可以帮助诊断阿尔茨海默氏病。为了设计新的成像剂，该成像剂用与淀粉样β斑块结合的发射正电子的铜64放射性核素进行了放射性标记，已经制备了带有附加的取代的1,2-二苯乙烯基官能团的双（thiosemicarbazone）配体家族。配体与铜（II）形成电荷中性且稳定的络合物。新的配体可以在室温下用64铜进行放射性标记。事实证明，两种先导复合物可与临床诊断为阿尔茨海默氏病的受试者的死后脑组织中存在的淀粉样蛋白-β斑块结合，并穿越小鼠的血脑屏障。本文介绍的工作提供了制备具有铜放射性核素的化合物的策略，该化合物可用于目标脑PET成像。
• [EN] 1,4-DISUBSTITUTED PIPERIDINE DERIVATIVES AND THEIR USE AS 11-BETAHSD1 INHIBITORS<br/>[FR] DERIVES DE PIPERIDINE 1,4 DISUBSTITUEE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE 11-BETAHSD1
  申请人：ASTRAZENECA AB

  公开号：WO2004033427A1

  公开（公告）日：2004-04-22

  The use of a compound of formula (I) in the manufacture of a medicament for use in the inhibition of 11βHSD1 is described.

  使用式(I)的化合物制造用于抑制11βHSD1的药物。
• Acetic Acid Accelerated Visible-Light Photoredox Catalyzed<i>N</i>-Demethylation of<i>N,N</i>-Dimethylaminophenyl Derivatives
  作者：Guolin Wu、Yazhen Li、Xuemei Yu、Yu Gao、Haijun Chen

  DOI：10.1002/adsc.201601108

  日期：2017.2.20

  N,N‐Dimethylaminophenyl moiety is a common fragment in medicinal chemistry as several pharmaceuticals bearing this privileged motif are on the market and under clinical evaluation. Oxidative N‐demethylation is generally regarded as the major metabolic pathway. However, pharmacokinetics, metabolites studies as well as the further structural modification are precluded by the impracticality of chemical

  N，N-二甲基氨基苯基部分是药物化学中的常见片段，因为带有这种特权基序的几种药物已在市场上出售并正在临床评估中。氧化性N-去甲基化通常被认为是主要的代谢途径。但是，化学合成的不切实际性排除了药代动力学，代谢产物的研究以及进一步的结构修饰。这里，我们报告，乙酸可以加速显著可见光photoredox催化Ñ的-demethylation N，N- -dimethylaminophenyl衍生物。这种方法很容易进行大规模反应，甚至可能用于潜在的工业生产。
• Iridium‐Catalysed Reductive Deoxygenation of Ketones with Formic Acid as Traceless Hydride Donor
  作者：Zhiheng Yang、Xueya Zhu、Shiyi Yang、Weiyan Cheng、Xiaojian Zhang、Zhanhui Yang

  DOI：10.1002/adsc.202000821

  日期：2020.12.8

  An iridium‐catalysed deoxygenation of ketones and aldehydes is achieved, with formic acid as hydride donor and water as co‐solvent. At low catalyst loading, a number of 4‐(N,N‐disubstituted amino) aryl ketones are readily deoxygenated in excellent yields and chemoselectivity. Numerous functional groups, especially phenolic and alcoholic hydroxyls, secondary amine, carboxylic acid, and alkyl chloride

  以甲酸为氢化物供体，水为助溶剂，实现了铱催化的酮和醛的脱氧。在低催化剂负载下，许多4-（N，N-二取代氨基）芳基酮易于脱氧，具有出色的收率和化学选择性。许多官能团，尤其是酚羟基和醇羟基，仲胺，羧酸和烷基氯，都具有良好的耐受性。当使用DCO 2 D和D 2 O代替它们的氢化对应物时，可获得双歧化的双链烷烃达90％。激活4‐（N，N已证明二取代氨基）芳基会经历各种有用的转化。脱氧氘已用于制备氘代药物分子Chlorambucil-4,4- d 2。
• Highly Efficient Binuclear Copper‐catalyzed Oxidation of <i>N,N</i> ‐Dimethylanilines with O ₂
  作者：Yuxia Liu、Yonggang Yan、Dong Xue、Zhongfu Wang、Jianliang Xiao、Chao Wang

  DOI：10.1002/cctc.201901962

  日期：2020.4.20

  A binuclear copper‐salicylate complex, [Cu(Sal)2(NCMe)]2 (Sal=salicylate), was found to be an active catalyst for the oxidation of N,N‐dimethylanilines by O2, affording the corresponding N‐methyl‐N‐phenylformamides as major products. The reactions were carried out with a O2 balloon and the S/C (substrate/catalyst ratio) of the model reaction could be up to 1×105, providing a practical and highly efficient

  发现双核水杨酸铜络合物[Cu（Sal）2（NCMe）] 2（Sal =水杨酸）是O 2氧化N，N-二甲基苯胺的活性催化剂，提供了相应的N-甲基‐ N ‐苯基甲酰胺为主要产品。将反应物用ö进行2气球和模型反应的S / C（底物/催化剂比率）可高达1×10 5，用于访问提供实际和高效催化协议Ñ甲基ñ -苯基甲酰胺。