N-(3-甲氧基苯基)-1-(4-甲氧基苯基)甲亚胺 | 99497-93-5

• 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: N-(3-甲氧基苯基)-1-(4-甲氧基苯基)甲亚胺
• 英文名称: (4-methoxybenzylidene)(3-methoxyphenyl)amine
• 英文别名: (4-methoxybenzylidene)-(3-methoxyphenyl)；p-Methoxybenzylidene-(3-methoxyphenyl)-amine；N-(3-methoxyphenyl)-1-(4-methoxyphenyl)methanimine
• CAS: 99497-93-5
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: MRZGJJVHNIMEDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  392.4±27.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)
• 保留指数：
  2296

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  N-(3-甲氧基苯基)-1-(4-甲氧基苯基)甲亚胺 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 生成 (3R,4S)-1-(3-Methoxy-phenyl)-4-(4-methoxy-phenyl)-3-(3-phenyl-propyl)-azetidin-2-one
  参考文献：
  名称：

  2-Azetidinone Cholesterol Absorption Inhibitors:  Structure−Activity Relationships on the Heterocyclic Nucleus

  摘要：

  A series of azetidinone cholesterol absorption inhibitors related to SCH 48461 ((-)-6) has been prepared, and compounds were evaluated for their ability to inhibit hepatic cholesteryl ester formation in a cholesterol-fed hamster model. Although originally designed as acyl CoA: cholesterol acyltransferase (ACAT) inhibitors, comparison of in vivo potency with in vitro activity in a microsomal ACAT assay indicates no correlation between activity in these two models. The molecular mechanism by which these compounds inhibit cholesterol absorption is unknown. Despite this limitation, examination of the in vivo activity of a range of compounds has revealed clear structure-activity relationships consistent with a well-defined molecular target. The details of these structure-activity relationships and their implications on the nature of the putative pharmacophore are discussed.

  DOI：

  10.1021/jm960405n
• 作为产物：
  描述：

  间氨基苯甲醚 、 4-甲氧基苯甲醛 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以100%的产率得到N-(3-甲氧基苯基)-1-(4-甲氧基苯基)甲亚胺
  参考文献：
  名称：

  Development of a scalable synthesis of P7C3-A20, a potent neuroprotective agent

  摘要：

  A scalable synthesis of the neuroprotective agent P7C3-A20 is described. The synthesis has provided hundred-gram batches of the final compound for biological evaluation in rodents and primates. The synthesis can be performed without chromatographic purification of intermediates or the final product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.024

文献信息

• N-Trialkylsilylimines as Coupling Partners for Pd-Catalyzed CN Bond-Forming Reactions: One-Step Synthesis of Imines and Azadienes from Aryl and Alkenyl Bromides
  作者：José Barluenga、Fernando Aznar、Carlos Valdés

  DOI：10.1002/anie.200352808

  日期：2004.1.5
• Nano-tube TiO2 as a new catalyst for eco-friendly synthesis of imines in sunlight
  作者：Mona Hosseini-Sarvari

  DOI：10.1016/j.cclet.2010.11.017

  日期：2011.5

  Nanomaterials are considered as suitable heterogeneous catalysts for many organic reactions. Herein nano-tube TiO2 has been reported as a heterogeneous catalyst, for synthesis of imines in sunlight at room temperature under solvent-free conditions. The condensation of less electrophilic carbonyl compounds with poorly nucleophilic amines was afforded imines in excellent yields. (c) 2010 Mona Hosseini-Sarvari. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• The protective effects of oxyresveratrol imine derivative against hydrogen peroxide-induced cell death in PC12 cells
  作者：J. Hur、S. Kim、P. Lee、Y. M. Lee、S. Y. Choi

  DOI：10.3109/10715762.2012.762769

  日期：2013.3

  Oxyresveratrol (2',3,4',5-tetrahydroxystilbene) is a naturally occurring ingredient found in mulberries that shows potential as an antioxidant, anti-inflammatory, and neuroprotective agent. This study was performed to identify materials similar to oxyresveratrol that may have more effective antioxidant properties. We synthesized a stilbene analog referred to as Compound 1(2',3,4',5-tetramethoxystilbene); a benzamide analog referred to as Compound 2 ((2,4-dimethoxyphenyl)-3,5-dimethoxybenzamide); and three imine analogs referred to as Compound 3 (3,5-dimethoxybenzylidene)-(2,4-dimethoxyphenylamine), Compound 4 ((4-methoxybenzylidene)-(3-methoxyphenyl) amine), and Compound 5 ((4-methoxybenzylidene) phenylamine). The cytoprotective effects of these compounds were subsequently evaluated using hydrogen peroxide-treated PC12 cells. The cytoprotective effects of the imine analogs were greater than the effects of oxyresveratrol and the other analogs at concentrations of 200 mu M. The Compound 3, which is the most effective imine analog of oxyresveratrol, exhibited these cytoprotective effects against hydrogen peroxide-induced oxidative stress through the regulation of heme oxygenase-1 (HO-1) expression and the translocation of nuclear factor E2-related factor 2 (Nrf2). Our results suggest that imine analogs of oxyresveratrol may be useful agents in reducing neuronal oxidative damage.
• 2-Azetidinone Cholesterol Absorption Inhibitors:  Structure−Activity Relationships on the Heterocyclic Nucleus
  作者：John W. Clader、Duane A. Burnett、Mary Ann Caplen、Martin S. Domalski、Sundeep Dugar、Wayne Vaccaro、Rosy Sher、Margaret E. Browne、Hongrong Zhao、Robert E. Burrier、Brian Salisbury、Harry R. Davis

  DOI：10.1021/jm960405n

  日期：1996.1.1

  A series of azetidinone cholesterol absorption inhibitors related to SCH 48461 ((-)-6) has been prepared, and compounds were evaluated for their ability to inhibit hepatic cholesteryl ester formation in a cholesterol-fed hamster model. Although originally designed as acyl CoA: cholesterol acyltransferase (ACAT) inhibitors, comparison of in vivo potency with in vitro activity in a microsomal ACAT assay indicates no correlation between activity in these two models. The molecular mechanism by which these compounds inhibit cholesterol absorption is unknown. Despite this limitation, examination of the in vivo activity of a range of compounds has revealed clear structure-activity relationships consistent with a well-defined molecular target. The details of these structure-activity relationships and their implications on the nature of the putative pharmacophore are discussed.
• Development of a scalable synthesis of P7C3-A20, a potent neuroprotective agent
  作者：Jacinth Naidoo、Christopher J. Bemben、Shawn R. Allwein、Jue Liang、Andrew A. Pieper、Joseph M. Ready

  DOI：10.1016/j.tetlet.2013.06.024

  日期：2013.8

  A scalable synthesis of the neuroprotective agent P7C3-A20 is described. The synthesis has provided hundred-gram batches of the final compound for biological evaluation in rodents and primates. The synthesis can be performed without chromatographic purification of intermediates or the final product. (C) 2013 Elsevier Ltd. All rights reserved.