4-二甲基氨基-2-甲氧基苯甲醛 | 84562-48-1

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-二甲基氨基-2-甲氧基苯甲醛
• 中文别名: 4-二甲氨基-2-甲氧基苯甲醛；4-二甲胺基-2-甲氧基苯甲醛
• 英文名称: 4-dimethylamino-2-methoxybenzaldehyde
• 英文别名: 2-methoxy-4-(dimethylamino)benzaldehyde；4-(dimethylamino)-2-methoxybenzaldehyde
• CAS: 84562-48-1
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD00151814
• 分子量: 179.219
• InChiKey: HGDRXADJVGVGBC-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60°C
• 沸点：
  150-152 °C(Press: 0.1 Torr)
• 密度：
  1.098±0.06 g/cm3(Predicted)
• 溶解度：
  25℃时微溶0.32g/L。
• 稳定性/保质期：
  按规定使用和贮存时不会分解，并应避免与氧化物、空气接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将药品存放在密闭、阴凉、干燥的地方。

反应信息

• 作为反应物：
  描述：

  4-二甲基氨基-2-甲氧基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 3-[7-(4-dimethylamino-2-methoxy-phenyl)-2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl]-4-hydroxy-6-methyl-pyran-2-one
  参考文献：
  名称：

  Discovery of 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7-phenyl-(E)-2,3,6,7-tetrahydro-1,4-thiazepines as a new series of apoptosis inducers using a cell- and caspase-based HTS assay

  摘要：

  We report the discovery of 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7-(4-methylphenyl)-(E)-2,3,6,7-tetrahydro-1,4-thiazepine (2a) as an inducer of apoptosis using our proprietary cell- and caspase-based HTS assay. Through structure activity relationship (SAR) studies, 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7-(2-methoxy-4-(methylthio)phenyl)-(E)-2,3,6,7-tetrahydro-1,4-thiazepine (5d) was identified as a potent apoptosis inducer with an EC50 value of 0.08 mu M in T47D cells, which was > 15-fold more potent than screening hit 2a. Compound 5d also was found to be highly active in a growth inhibition assay with a GI(50) value of 0.05 mu M in T47D cells and to function as an inhibitor of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.098
• 作为产物：
  描述：

  溴甲烷 、 4-(二甲氨基)邻羟苄基 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以68.1%的产率得到4-二甲基氨基-2-甲氧基苯甲醛
  参考文献：
  名称：

  Effect of phenyl ring substitution on J-aggregate formation ability of novel bisazomethine dyes in vapour-deposited films

  摘要：

  Bisazomethine dyes, which are synthesized using diaminomaleonitrile and aminobenzaldehydes, exhibit red fluorescence in solution and in the solid state. Several bisazomethine dyes are known to form J-aggregates in vapour-deposited films. In this work, novel bisazomethine dyes were synthesized and the effect of phenyl ring substitution on the J-aggregate formation in vapour-deposited films was examined. The optical properties of the dyes were examined in solution and in the solid state through molecular orbital calculations. Four derivatives were found to form J-aggregates in vapour-deposited films as determined from the shape of the spectrum and the absorption edge. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.11.009

文献信息

• Novel Thiophene Derivatives as Spingosine-1-Phosphate-1 Receptor Agonists
  申请人：Bolli Martin

  公开号：US20080194670A1

  公开（公告）日：2008-08-14

  The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.

  这项发明涉及新型噻吩衍生物，它们的制备以及它们作为药用活性化合物的用途。这些化合物特别作为免疫抑制剂。
• [EN] USE OF AND SOME NOVEL IMIDAZOPYRIDINES<br/>[FR] NOUVELLES IMIDAZOPYRIDINES ET LEUR UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2004016611A1

  公开（公告）日：2004-02-26

  The use of compounds of formula (I) wherein R1, R3, R10, m and Ar are as defined in the Specification and pharmaceutically acceptable salts thereof in the manufacture of a medicament for the treatment or prophylaxis of diseases or conditions in which inhibition of kinase Itk activity is beneficial is disclosed. Certain novel compounds of formula (I), together with processes for their preparation, compositions containing them and their use in therapy are also disclosed.

  公开了在制备药物用于治疗或预防抑制激酶Itk活性有益的疾病或症状中，使用式(I)中R1、R3、R10、m和Ar所定义的化合物及其药学上可接受的盐。还公开了式(I)的某些新化合物，以及它们的制备方法、含有它们的组合物和它们在治疗中的用途。
• Cobalt-catalysed C–H methylation for late-stage drug diversification
  作者：Stig D. Friis、Magnus J. Johansson、Lutz Ackermann

  DOI：10.1038/s41557-020-0475-7

  日期：2020.6

  despite its significance, accessing such analogues via derivatization at a late stage remains a pivotal challenge. In an effort to mitigate this major limitation, we here present a strategy for the cobalt-catalysed late-stage C–H methylation of structurally complex drug molecules. Enabling broad applicability, the transformation relies on a boron-based methyl source and takes advantage of inherently present

  神奇的甲基效应在药物化学中广为人知，但尽管意义重大，但在后期通过衍生化获得此类类似物仍然是一项关键挑战。为了减轻这一主要限制，我们在此提出了一种策略，用于对结构复杂的药物分子进行钴催化的后期C–H甲基化。这种转化具有广泛的适用性，它依赖于基于硼的甲基源，并利用固有存在的官能团来引导C–H活化。确定在不同功能类别下观察到的相对反应性，并在各种反应条件下测试转化对一组常见功能基序的敏感性。无需预功能化或后脱保护，市场上出售的各种药物分子和天然产物可以以可预测的方式甲基化。随后的理化和生物学测试证实了这种看似微小的结构变化可影响重要药物特性的程度。
• Monofluoroalkenylation of Dimethylamino Compounds through Radical–Radical Cross‐Coupling
  作者：Jin Xie、Jintao Yu、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/anie.201602347

  日期：2016.8

  An unprecedented and challenging radical–radical cross‐coupling of α‐aminoalkyl radicals with monofluoroalkenyl radicals derived from gem‐difluoroalkenes was achieved. This first example of tandem C(sp3)−H and C(sp2)−F bond functionalization through visible‐light photoredox catalysis offers a facile and flexible access to privileged tetrasubstituted monofluoroalkenes under very mild reaction conditions

  实现了前所未有的，具有挑战性的α-氨基烷基自由基与衍生自双二氟烯烃的单氟烯基自由基的自由基自由基偶联。通过可见光光氧化还原催化作用的串联C（sp 3）-H和C（sp 2）-F键功能化的第一个例子提供了在非常温和的反应条件下轻松灵活地访问特权四取代的单氟烯烃的方法。这种氧化还原中性方法在范围，功能基团耐受性和区域选择性方面的显着特征可以通过复杂分子结构的晚期氟烯基化来说明，例如生物活性（+）-地尔硫ze，罗格列酮，二氢青蒿素，齐墩果酸和雄甾酮衍生物，代表重要的新α-氨基CH单氟烯基化反应。
• Improved PeT Molecules for Optically Sensing Voltage in Neurons
  作者：Clifford R. Woodford、E. Paxon Frady、Richard S. Smith、Benjamin Morey、Gabriele Canzi、Sakina F. Palida、Ricardo C. Araneda、William B. Kristan、Clifford P. Kubiak、Evan W. Miller、Roger Y. Tsien

  DOI：10.1021/ja510602z

  日期：2015.2.11

  VoltageFluor (VF) dyes have the potential to measure voltage optically in excitable membranes with a combination of high spatial and temporal resolution essential to better characterize the voltage dynamics of large groups of excitable cells. VF dyes sense voltage with high speed and sensitivity using photoinduced electron transfer (PeT) through a conjugated molecular wire. We show that tuning the

  VoltageFluor (VF) 染料具有在可兴奋膜中光学测量电压的潜力，结合高空间和时间分辨率，对于更好地表征大群可兴奋细胞的电压动态至关重要。VF 染料通过共轭分子线使用光诱导电子转移 (PeT) 以高速和灵敏的方式检测电压。我们表明，通过系统的化学取代调整 PeT (ΔGPeT + w) 的驱动力可以调节电压灵敏度，根据实验测量的氧化还原电位估计 (ΔGPeT + w) 值，并验证膜片钳 HEK 电池中 10 个新 VF 的电压敏感性染料。VF2.1(OMe).H，每 100 mV 的 ΔF/F 为 48%，在 HEK 细胞、分离的大鼠皮质神经元和药用水蛭神经节中显示出比以前的染料提高了大约 2 倍。此外，

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