1-(2-萘)-1H-吡咯-2,5-二酮 | 6637-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(2-萘)-1H-吡咯-2,5-二酮
• 中文别名: 1-(2-萘基)-1H-吡咯-2,5-二酮
• 英文名称: 1-(naphthalen-2-yl)-1H-pyrrole-2,5-dione
• 英文别名: N-2-naphthylmaleimide；N-[2]naphthyl-maleimide；N-[2]Naphthyl-maleinimid；N-(β-Naphthyl)-maleinimid；1-(2-Naphthalenyl)-1H-pyrrole-2,5-dione；1-naphthalen-2-ylpyrrole-2,5-dione
• CAS: 6637-45-2
• 化学式: C₁₄H₉NO₂
• mdl: MFCD00443960
• 分子量: 223.231
• InChiKey: ISPTVBCAVIHHEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  1-(2-萘)-1H-吡咯-2,5-二酮 以 硝基苯 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  Abdou, Sadek E.; Habashy, Adiba; Aziz, Gamil, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 9, p. 755 - 758

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(naphthalen-2-ylamino)-4-oxobut-2-enoic acid 在 sodium acetate 、 乙酸酐 作用下， 反应 2.0h， 生成 1-(2-萘)-1H-吡咯-2,5-二酮
  参考文献：
  名称：

  Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

  摘要：

  Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 +/- 1.3, 5.1 +/- 3.4, 16.2 +/- 5.4, and 19.0 +/- 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 +/- 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at SO mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

  DOI：

  10.1021/acs.jafc.6b02250

文献信息

• [DE] PYRAZOLINOLE ALS PESTIZIDE<br/>[EN] PYRAZOLINOLS USED AS PESTICIDES<br/>[FR] PYRAZOLINOLES UTILISEES EN TANT QUE PESTICIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2005058838A1

  公开（公告）日：2005-06-30

  Verwendung von Pyrazolinolen Formel (I) in welcher A, Q, R1, R2, R3, R4 und R5 die in der Beschreibung angegebenen Bedeutungen haben, zum Bekämpfen von Schädlingen, neue Pyrazolinole und mehrere Verfahren zum Herstellen dieser Stoffe.

  在这个公式（I）中使用吡唑烯醇（Pyrazolinolen），其中A、Q、R1、R2、R3、R4和R5具有描述中指定的含义，用于对抗害虫，以及制造这些化合物的新的吡唑烯醇和多种制备方法。
• Synthesis of pyrrolo[3,4-d]isoxazolines via a one-pot radical functionalization/cycloaddition of methyl ketone, tert-butyl nitrite, and maleimide
  作者：Hang Wang、Rui Cheng、Gangqiang Wang、Yang Shi、Jian Wang、Haibing Guo、Leslie Trigoura、Yalan Xing、Shaofa Sun

  DOI：10.1016/j.tetlet.2020.151652

  日期：2020.3

  The development of tandem radical Csp3-H functionalization/ cycloaddition of methyl ketone, tert-butyl nitrite, and maleimide has been reported herein. A variety of pyrrolo[3,4-d]isoxazolines have been successfully synthesized under metal-free conditions with excellent functional group compatibility. X-ray crystallography of the pyrrolo[3,4-d]isoxazoline was obtained and the reaction mechanism was

  本文已经报道了甲基酮，亚硝酸叔丁酯和马来酰亚胺的串联自由基Csp 3 -H官能化/环加成的发展。在无金属条件下，具有出色的官能团相容性，已成功合成了多种吡咯并[3,4-d]异恶唑啉。获得了吡咯并[3,4-d]异恶唑啉的X射线晶体学分析，并提出了反应机理。
• Breaking Symmetry with Symmetry: Bifacial Selectivity in the Asymmetric Cycloaddition of Anthracene Derivatives
  作者：Carles Rodríguez-Escrich、Rebecca L. Davis、Hao Jiang、Julian Stiller、Tore K. Johansen、Karl Anker Jørgensen

  DOI：10.1002/chem.201300142

  日期：2013.2.25

  Push to activate: A new catalytic strategy for the activation of anthracene derivatives has been developed. From symmetrical starting materials, enantioselective cycloaddition reactions can be achieved by employing a C2‐symmetric aminocatalyst. This selectivity is due to the gain or loss of conjugation between the enamine and the anthracene in the two transition‐state structures. This methodology is demonstrated

  推动活化：已开发出用于活化蒽衍生物的新催化策略。从对称的起始原料，可以通过使用C 2对称的氨基催化剂来实现对映选择性的环加成反应。这种选择性是由于两个过渡态结构中烯胺和蒽之间共轭的得失所致。在14个示例中证明了该方法，其产率为70-96％，ee为76-95％  。
• Synthesis of CHF₂-substituted 3-azabicyclo[3.1.0]hexanes by photochemical decomposition of CHF₂-pyrazolines
  作者：Yang Zheng、Xinling Yu、Songyang Lv、Pavel K. Mykhailiuk、Qiang Ma、Li Hai、Yong Wu

  DOI：10.1039/c7ra13141k

  日期：——

  A practical synthesis of CHF2-substituted 3-azabicyclo[3.1.0]hexanes was developed for the first time. The key step was photochemical decomposition of CHF2-substituted pyrazolines. This protocol has the advantages of simple operation, and mild conditions, as well as excellent functional group tolerance, giving the desired products in moderate to excellent yields.

  首次开发了CHF 2取代的3-氮杂双环[3.1.0]己烷的实用合成方法。关键步骤是CHF 2 -取代的吡唑啉的光化学分解。该方案具有操作简单、条件温和、官能团耐受性好等优点，能够以中等至优异的产量提供所需的产品。
• Photocatalyzed Reverse Polarity Oxidative Povarov Reaction of Glycine Derivatives with Maleimides
  作者：Yongxin Zhang、Wei Jiang、Xiazhen Bao、Yifeng Qiu、Yong Yuan、Caixia Yang、Congde Huo

  DOI：10.1002/cjoc.202100401

  日期：2021.12

  An oxidative tandem (4+2)-cyclization/aromatization of N-aryl glycine derivatives with electron-deficient alkenes was first achieved using Ru(bpy)3Cl2 as a photocatalyst and TBHP as an oxidant in combination with visible-light irradiation by blue LEDs. One-electron oxidation and the following α-deprotonation of glycine derivatives afford α-amino alkyl radicals, which were then trapped by electrophilic

  使用 Ru(bpy) 3 Cl 2作为光催化剂和 TBHP 作为氧化剂，结合可见光照射，首次实现了N-芳基甘氨酸衍生物与缺电子烯烃的氧化串联 (4+2)-环化/芳构化蓝色 LED。单电子氧化和随后的甘氨酸衍生物的 α-去质子化得到 α-氨基烷基自由基，然后被亲电马来酰亚胺捕获。作为一种原子经济高效的方法，在温和的反应条件下，以良好的收率获得了多种吡咯并[3,4- c ]喹啉-1,3-二酮。