5-(4-methoxyphenylimino)-5H-furan-2-one | 19990-24-0

• 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: 5-(4-methoxyphenylimino)-5H-furan-2-one
• 英文别名: maleic acid N-(4-methoxyphenyl)isoimide；5-[N-(4-methoxyphenyl)-imino]-5H-furan-2-one；N-(4-Methoxyphenyl)-maleisoimid；4'-Methoxyisomaleanilide；N-(4-Methoxyphenyl)-maleinisoimid；5-(4-Methoxyphenyl)iminofuran-2-one
• CAS: 19990-24-0
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: FSLOMWIJWIXRQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methoxyphenylimino)-5H-furan-2-one 、 环己甲酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 1-<4-Methoxy-phenyl>-3,3-pentamethylen-5-oxa-1-aza-spiro<3,4>oct-7-en-2,6-dion
  参考文献：
  名称：

  螺-β-内酯durch [2 + 2]-环加成酮酮的内酯†

  摘要：

  酮基的[2 + 2]-环加成反应成氨基内酯的螺-β-内酰胺

  DOI：

  10.1002/hlca.19790620625
• 作为产物：
  描述：

  N-(4-甲氧基苯基)马来酸 在 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-(4-methoxyphenylimino)-5H-furan-2-one
  参考文献：
  名称：

  含有细胞毒性 1,4-dioxo-2-butenyl 药效团的芳胺衍生物

  摘要：

  已制备了若干系列含有 1,4-二氧-2-丁烯基部分的化合物作为候选细胞毒素，包括N-芳基马来酸甲酯、N-芳基富马酸甲酯和N-芳基马来酰亚胺。此外，合成了N-芳基异马来酰亚胺，它是N-芳基马来酰亚胺的结构异构体。这些化合物针对人 Molt 4/C8 和 CEM T 淋巴细胞以及鼠 L1210 细胞进行了评估。N-芳基富马酸甲酯显示出最高的细胞毒性效力，尤其是甲基N-(3,4-二氯苯基)富马酸盐对 L1210 细胞的作用是马法兰的六倍，在 Molt 4/C8 试验中与该药物等效。通过使用模型苄基硫醇对代表性化合物进行硫醇化来证明所研究化合物的亲电性。甲基ñ - （3,4-二氯苯基）fumaramate和甲基ñ - （4-氯苯基）马来酰胺酸抑制人Ñ -myristoyltransferase，可能的分子靶标，在高微摩尔范围。QSAR 和分子建模揭示了许多分子的不同结构特征与细胞毒性效力之间的一些

  DOI：

  10.1016/j.bmcl.2010.01.098

文献信息

• Acetylcholinesterase inhibition by products generated in situ from the transformation of N-arylisomaleimides
  作者：Juan A. Guevara、José G. Trujillo、Delia Quintana、Hugo A. Jiménez、Mónica G. Arellano、José R. Bahena、Feliciano Tamay、Fabiola J. Ciprés

  DOI：10.1007/s00044-017-2122-4

  日期：2018.3

  the transformation reaction proved to be influenced by electronic effects. This was demonstrated qualitatively by 1H NMR spectroscopy and quantitatively by monitoring the kinetic of isomerization of N-phenylisomaleimide to N-phenylmaleimide. Subsequently, the first pseudo-order and activation energy (E a) of the process were determined. The compounds showed in situ influence on AChE inhibition. The derivatives

  当N-芳基异马来酰亚胺在酶促反应条件下转化时，转化反应被证明受电子效应的影响。通过1 H NMR光谱定性地证明了这一点，并且通过监测N-苯基异马来酰亚胺向N-苯基马来酰亚胺的异构化动力学定量地证明了这一点。随后，第一伪阶和活化能（E a）的过程已确定。这些化合物对AChE抑制作用具有原位影响。具有吸电子基团的衍生物表现出比具有供电子基团的衍生物更好的效果。电子实验表明配体评估了与CAS位点之间已建立的相互作用。这表明这些化合物可用于产生更好的可逆和竞争性AChE抑制剂。
• Cyanuric chloride: decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides
  作者：Kishan P. Haval、Santosh B. Mhaske、Narshinha P. Argade

  DOI：10.1016/j.tet.2005.10.027

  日期：2006.1

  Starting from maleanitic and maleamic acids, a facile general approach to kinetically controlled isomaleimides has been described for the first time using cyanuric chloride as a dehydrating agent with 85-98% yields. The effect of a variety of substituents present on the aromatic ring in amine and maleic anhydride moiety, on these kinetic/thermodynamic dehydration processes of anilic acids has been also described. Under the same set of reaction conditions the phthalanilic acid gave kinetically controlled product, isoplitalimide in 91% yield, while the corresponding succinanilic acid furnished the thermodynamically more stable succinimide in high yield. (c) 2005 Elsevier Ltd. All rights reserved.
• Reactions of o-aminothiophenol withαβ-unsaturated dicarbonyl systems. Facile synthesis of benzothiazines and benzothiazepines
  作者：V. Balasubramaniyan、P. Balasubramaniyan、A.S. Shaikh

  DOI：10.1016/s0040-4020(01)90560-5

  日期：1986.1
• Propanephosphonic Acid Anhydride–Mediated Cyclodehydration of Maleic Acid Monoamides
  作者：Igors Klimenkovs、Eduards Bakis、Anda Priksane

  DOI：10.1080/00397911.2012.727060

  日期：2013.10.2

  Propanephosphonic acid anhydride (T3P) has been proposed as a novel reagent for the preparation of maleic acid isoimides from the corresponding monoamides. A series of substituted aromatic and aliphatic isoimides have been prepared in good yields. The main advantage of this synthetic method is the use of environmentally benign, cost-efficient reagents and solvents, which are also safer to handle than the ones employed previously. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.