N-(4-乙氧基苯基)-1-(4-甲氧基苯基)甲亚胺 | 15475-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-(4-乙氧基苯基)-1-(4-甲氧基苯基)甲亚胺
• 英文名称: p-anisal-p-phenetidine
• 英文别名: 4-ethoxyphenyl-N-(4-methoxybenzylidene)amine；(4-methoxybenzylidene)(4-ethoxyphenyl)amine；(4-methoxybenzylidene)-4-ethoxyaniline；N-(4-methoxy-benzylidene)-p-phenetidine；N-(4-Methoxy-benzyliden)-p-phenetidin；4-Methoxy-benzaldehyd-(4-aethoxy-phenylimin)；p-Methoxybenzylidene-(4-ethoxyphenyl)-amine；N-(4-ethoxyphenyl)-1-(4-methoxyphenyl)methanimine
• CAS: 15475-06-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: QFRLSYNEBYPEHA-UHFFFAOYSA-N

物化性质

• 熔点：
  128.5 °C
• 沸点：
  401.9±30.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)
• 保留指数：
  2372

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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-(4-乙氧基苯基)-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-(4-ethoxyphenyl)-4-(4-methoxyphenyl)-3-(3-phenylpropyl)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：

  4-甲氧基苯甲醛 、 对乙氧基苯胺 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-(4-乙氧基苯基)-1-(4-甲氧基苯基)甲亚胺
  参考文献：
  名称：

  使用氯磷酸二乙酯一锅法合成 azetidin-2-one

  摘要：

  描述了通过 [2+2] 环加成反应，在氯磷酸二乙酯存在下，通过胺和醛的预混合物与羧酸的反应，简单方便地合成 2-氮杂环丁酮衍生物。不需要将亚胺作为中间体进行分离和纯化。该方法操作方便，通过简单的纯化即可获得高产率的产品。

  DOI：

  10.3184/174751912x13282660033937

文献信息

• A facile and effective synthesis of 2-azetidinones via phosphonitrilic chloride
  作者：Maaroof Zarei

  DOI：10.1016/j.tet.2013.05.121

  日期：2013.8

  The Staudinger reaction of imines to β-lactams was successfully achieved with substituted acetic acid and phosphonitrilic chloride in one-pot under mild conditions. Several types of β-lactams, especially 3-electron-withdrawing group β-lactams, can be synthesized by this versatile and efficient method in good to excellent yields. This method is simple, clean, and the by-products were removed by simple

  在温和的条件下，在一锅中成功地用取代的乙酸和磷腈氯化物成功实现了亚胺对β-内酰胺的施陶丁格反应。通过这种通用且有效的方法，可以以良好或优异的产率合成几种类型的β-内酰胺，尤其是3个吸电子基团β-内酰胺。该方法简单，清洁，并且通过简单的水后处理除去了副产物。考虑了溶剂，试剂的摩尔比和温度的影响。
• One-step Synthesis of β-lactams Using Cyanuric Fluoride
  作者：Maaroof Zarei

  DOI：10.3184/174751912x13545429290478

  日期：2013.1

  Cyanuric fluoride works as an efficient acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acids and imines in a one-pot synthesis under mild conditions. The yields are good to excellent and the reaction conditions are mild, simple and efficient.

  氟化氰是一种高效的酸活化剂试剂，可在温和的条件下进行取代乙酸和亚胺的直接[2+2]酮-亚胺环化反应。反应条件温和、简单、高效，产率从良好到极佳。
• An efficient and green method for the synthesis of 2-azetidinones mediated by propylphosphonic anhydride (T3P®)
  作者：Maaroof Zarei

  DOI：10.1007/s00706-014-1217-6

  日期：2014.9

  acids and imines using propylphosphonic anhydride (T3P®) as acid activator under mild and clean conditions. Monocyclic, spirocyclic and 3-electron-withdrawing group β-lactams were synthesized by this method and optimization of conditions were performed. Graphical abstract

  摘要一系列的2-氮杂环丁酮已在良好由[2 + 2]的使用丙基膦酸酐（T3P取代的乙酸和亚胺烯酮亚胺环加成制备到优异的产率®）为轻度和清洁的条件下酸活化剂。用这种方法合成了单环，螺环和3个吸电子基团β-内酰胺，并进行了条件优化。 图形概要
• Synthesis of Structurally Diverse 2-Azetidinones via Staudinger Reaction on a Solid Support
  作者：Aliasghar Jarrahpour、Abdolhamid Fadavi、Maaroof Zarei

  DOI：10.1246/bcsj.20100212

  日期：2011.3.15

  Trimellitic anhydride was attached to Merrifield resin and a ketene was generated from polymer-bound phthaloylglycine. Then this polymer reacted with imines in the presence of Vilsmeier reagent and triethylamine to afford the solid-phase-tethered β-lactam products. Selective cleavage of supported β-lactams by trifluoroacetic acid and methylhydrazine gave 4-carboxyphthalimido- and 3-amino-β-lactams, respectively. The trans-stereochemistry was found in all products.

  偏苯三酸酐与Merrifield树脂结合，并通过聚合物结合的邻苯二甲酰甘氨酸生成了酮烯。然后，在Vilsmeier试剂和三乙胺的存在下，该聚合物与亚胺反应，得到固相连接的β-内酰胺产物。通过三氟乙酸和甲基肼的选择性断裂，分别得到了4-羧基邻苯二甲酰亚氨基-和3-氨基-β-内酰胺。所有产物均发现反式立体化学结构。
• An Easy and Convenient Synthesis of β-Lactams via a One-Pot Staudinger Reaction with 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride Starting from Substituted Carboxylic Acids
  作者：Maaroof Zarei

  DOI：10.2174/1570178611666141201224959

  日期：2015.1.1

  An easy and convenient direct synthesis of 2-azetidinones is described. The [2+2] cycloaddition reaction of imines and carboxylic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) has been employed to synthesize a variety of 2-azetidinones in high yields. The products were easily isolated because the byproducts are highly soluble in water.

  报道了一种简单便捷的2-氮杂环丁酮的直接合成方法。通过4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯盐（DMTMM）催化亚胺和羧酸的[2+2]环加成反应，实现了一系列2-氮杂环丁酮的高产率合成。产物易于分离，因为副产物在水中具有很高的溶解性。