[1-(2,5-Dimethoxy-phenyl)-meth-(Z)-ylidene]-methyl-amine | 114943-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1-(2,5-Dimethoxy-phenyl)-meth-(Z)-ylidene]-methyl-amine
• 英文别名: 1-(2,5-dimethoxyphenyl)-N-methylmethanimine
• CAS: 114943-72-5
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: GMUJBJRFXFDHON-UHFFFAOYSA-N

物化性质

• 沸点：
  300.7±32.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

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：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1-(2,5-Dimethoxy-phenyl)-meth-(Z)-ylidene]-methyl-amine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以100%的产率得到1-(2,5-二甲氧基苯基)-n-甲基甲胺
  参考文献：
  名称：

  Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones

  摘要：

  In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbarnic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC50 values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.026
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 、 甲胺 在 sodium sulfate 作用下， 以 氯仿 、 水 为溶剂， 生成 [1-(2,5-Dimethoxy-phenyl)-meth-(Z)-ylidene]-methyl-amine
  参考文献：
  名称：

  Keto-Analogs of Arylidene-Imidazolones as Fluorogenic Dyes

  摘要：

  摘要 我们报告了一系列(Z)-2-乙酰基-4-亚苄基-1-甲基-1Н-咪唑-5(4Н)-酮，其荧光强度的变化明显依赖于溶剂。通过引入 2-乙酰基，可以将吸收和发射最大值转移到长波长区域。我们已经证明，这些化合物可用于荧光显微镜下内质网的染色。

  DOI：

  10.1134/s1068162022060243

文献信息

• Efficient Synthesis of New 4-Arylideneimidazolin-5-ones Related to the GFP Chromophore by 2+3 Cyclocondensation of Arylideneimines with Imidate Ylides
  作者：Janusz Kowalik、Anthony Baldridge、Laren Tolbert

  DOI：10.1055/s-0029-1218796

  日期：2010.7

  A 2+3 condensation of a wide assortment of Schiff bases, prepared from aromatic aldehydes and primary amines, with methyl 2-(1-ethoxyethylideneamino)acetate allows convenient access to an extensive family of substituted 4-arylideneimidazolin-5-one analogues of the green fluorescent protein (GFP) chromophore. 4-arylideneimidazolin-5-one - azomethine ylide - Schiff bases - heterocycle - 2+3 cycloaddition

  由芳族醛和伯胺制得的各种席夫碱与2-（1-乙氧基乙叉基氨基）乙酸甲酯的2 + 3缩合反应可方便地获得广泛的取代的4-芳基亚氨基咪唑啉-5-酮类似物家族绿色荧光蛋白（GFP）生色团。 4-芳基亚胺达唑啉-5-酮-甲亚胺叶立德-席夫碱-杂环-2 + 3环加成
• Isoquinolinium salt syntheses from cyclopalladated benzaldimines and alkynes
  作者：Guangzhong Wu、Steven J. Geib、Arnold L. Rheingold、Richard F. Heck

  DOI：10.1021/jo00249a018

  日期：1988.7
• Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones
  作者：Lorna Piazzi、Federica Belluti、Alessandra Bisi、Silvia Gobbi、Stefano Rizzo、Manuela Bartolini、Vincenza Andrisano、Maurizio Recanatini、Angela Rampa

  DOI：10.1016/j.bmc.2006.09.026

  日期：2007.1.1

  In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbarnic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC50 values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases. (c) 2006 Elsevier Ltd. All rights reserved.
• Keto-Analogs of Arylidene-Imidazolones as Fluorogenic Dyes
  作者：A. I. Sokolov、A. A. Gorshkova、N. S. Baleeva、M. S. Baranov

  DOI：10.1134/s1068162022060243

  日期：2022.12

  We report a series of (Z)-2-acetyl-4-benzyliden-1-methyl-1Н-imidazol-5(4Н)-ones with a pronounced solvent-dependent intensity of fluorescence variation. The introduction of the 2-acetyl group allows one to shift the absorption and emission maxima to the long-wavelength region. We have shown that these compounds can be used for staining the endoplasmic reticulum for fluorescent microscopy.

  摘要 我们报告了一系列(Z)-2-乙酰基-4-亚苄基-1-甲基-1Н-咪唑-5(4Н)-酮，其荧光强度的变化明显依赖于溶剂。通过引入 2-乙酰基，可以将吸收和发射最大值转移到长波长区域。我们已经证明，这些化合物可用于荧光显微镜下内质网的染色。