3-(4-氯苯基)吡咯烷-2,5-二酮 | 1628-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 3-(4-氯苯基)吡咯烷-2,5-二酮
• 英文名称: 3-(4-chlorophenyl)-pyrrolidine-2,5-dione
• 英文别名: (+/-)-(4-Chlorphenyl)-bernsteinsaeureimid；2-(4-Chlorophenyl)succinimide；3-(4-chlorophenyl)pyrrolidine-2,5-dione
• CAS: 1628-19-9
• 化学式: C₁₀H₈ClNO₂
• 分子量: 209.632
• InChiKey: KYCZWRCDGYAFHA-UHFFFAOYSA-N

物化性质

• 沸点：
  410.2±45.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-氯苯基)吡咯烷-2,5-二酮 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以33%的产率得到3-(4-氯苯基)吡咯烷
  参考文献：
  名称：

  Metabolism of 3-(p-chlorophenyl)pyrrolidine. Structural effects in conversion of a prototype .gamma.-aminobutyric acid prodrug to lactam and .gamma.-aminobutyric acid type metabolites

  摘要：

  By use of rat liver or brain homogenate supernatants containing microsomes and/or mitochondria, it was found that the prototype GABAergic prodrug [3-(p-chlorophenyl)pyrrolidine (1)] underwent a series of alpha-oxidation transformations to a pair of amino acid metabolites and a pair of lactam metabolites [4-amino-3-(p-chlorophenyl)butanoic acid, baclofen (5); 4-amino-2-(p-chlorophenyl)butanoic acid (10); 4-(chlorophenyl)pyrrolidin-2-one and 3-(p-chlorophenyl)pyrrolidine-2-one (11)]. With the liver homogenates, the formation of the lactam metabolites was approximately 2 orders of magnitude greater than that of the amino acid metabolites, while with the brain homogenates, the amino acid and lactam pathways were of similar magnitude. For either tissue, for both the lactam and the amino acid series, attack at the less sterically hindered 5-position of the pyrrolidine ring was greater than the attack at the 2-position (5 greater than 10 and 6 greater than 11) with the exception of the liver homogenate mitochondrial fraction (6 less than 11). The parenteral administration of the prodrug 1 was found to give detectable brain levels of 5 as well as activity in an isoniazid-induced (GABA-inhibited) convulsion model.

  DOI：

  10.1021/jm00126a033
• 作为产物：
  描述：

  对氯苯乙腈 在 盐酸 、 sodium hydroxide 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 3-(4-氯苯基)吡咯烷-2,5-二酮
  参考文献：
  名称：

  Synthesis of 3-Methylthio-4-aryl-3-pyrroline-2,5-diones and 3-Arylpyrrolidine-2,5-diones by Reaction of Nitroketene Dithioacetal with Arylacetonitriles

  摘要：

  The reaction of nitroketene dithioacetal (1a), i.e., 2,2-bis(methylthio)-1-nitroethylene, with arylacetonitriles (2a-I) in the presence of the base like sodium hydroxide gave 4-nitrobut-2-enenitriles (3a-I) which were converted into 5-hydroxyimino-4-methylthio-3-phenyl-3-pyrrolin-2-ones (4a-i) under refluxing in methanol. Title compounds (5a-i) were readily obtained by the treatment of 4a-i with hydrochloric acid and were finally led to N-methylated products (6a-I) with methyl iodide. The reduction of maleimides (4-6) with zinc dust in acetic acid afforded the corresponding 3-arylpyrrolidine-2,5-diones (7a-i) that can be converted to pharmacologycally active compounds like mesembrines.

  DOI：

  10.3987/com-01-9336

文献信息

• Pharmacochemistry of Novel Aminoketone Phthalimide, Δ4-Tetrahydrophthalimide, and Arylsuccinimide Derivatives with Local Anaesthetic Activity
  作者：Eleni Sotiropoulou、Panos N. Kourounakis

  DOI：10.1002/ardp.19943270104

  日期：——

  prospective local anaesthetic activity were prepared. The structure of the synthesized compounds was confirmed by spectroscopic and elemental analyses. The physicochemical parameters (pka and logP) were also investigated. The local anaesthetic activity was determined in vitro on sciatic frog's nerve by the compound action potential technique: the phthalimide derivatives possess considerable local anaesthetic

  制备了许多具有预期局部麻醉活性的氨基酮。通过光谱和元素分析确认合成化合物的结构。还研究了理化参数(pka和logP)。采用复合动作电位技术体外测定坐骨蛙神经的局麻活性：邻苯二甲酰亚胺衍生物具有与利多卡因相当而高于普鲁卡因的相当大的局麻活性。
• Design, synthesis and anticonvulsant properties of new N-Mannich bases derived from 3-phenylpyrrolidine-2,5-diones
  作者：Krzysztof Kamiński、Jolanta Obniska、Iwona Chlebek、Beata Wiklik、Sabina Rzepka

  DOI：10.1016/j.bmc.2013.07.029

  日期：2013.11

  The synthesis and anticonvulsant properties of new N-Mannich bases of 3-phenyl- (9a–d), 3-(2-chlorophenyl)- (10a–d), 3-(3-chlorophenyl)- (11a–d) and 3-(4-chlorophenyl)-pyrrolidine-2,5-diones (12a–d) were described. The key synthetic strategies involve the formation of 3-substituted pyrrolidine-2,5-diones (5–8), and then aminoalkylation reaction (Mannich-type) with formaldehyde and corresponding secondary

  的新的合成和抗惊厥性质N- -3-苯基的曼尼希碱（9A - d），3-（2-氯苯基） - （10A - d），3-（3-氯苯基） - （11A - d）和描述了3-（4-氯苯基）-吡咯烷-2,5-二酮（12a – d）。键合成策略涉及3-取代的吡咯烷-2,5-二酮类（形成5 - 8），然后氨基烷基反应（曼尼希型）与甲醛和相应的仲胺，其让以获得最终化合物9A - d，10a – d，11a – d和12a – d的产量很高。使用最大电击（MES）和皮下戊四氮（sc PTZ）癫痫发作试验对小鼠（ip）进行初始抗惊厥筛选。在大鼠中口服给药后，对小鼠中最有效的化合物进行了测试。急性神经毒性是通过最小运动障碍旋转试验来确定的。体内结果显示，许多化合物尤其在MES测试（人类强直性阵挛性癫痫发作模型）中有效。在大鼠的MES发作中最活跃的是1-[（4-苄基-1-哌啶基）甲基] -3-（2-氯苯基）吡咯烷-2
• Synthesis and Anticonvulsant Properties of New Mannich Bases Derived from 3-Aryl-pyrrolidine-2,5-diones. Part 1
  作者：Jolanta Obniska、Maciej Kopytko、Agnieszka Zagórska、Iwona Chlebek、Krzysztof Kamiński

  DOI：10.1002/ardp.200900250

  日期：——

  series of new Mannich bases of N‐[(4‐arylpiperazin‐1‐yl)‐methyl]‐3‐(chlorophenyl)‐pyrrolidine‐2,5‐diones 10–23 have been synthesized and evaluated for their anticonvulsant activity in maximum electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure threshold tests. Their neurotoxicity was determined using a rotorod screen. Several molecules showed a promising anticonvulsant profile especially

  合成了一系列N-[(4-芳基哌嗪-1-基)-甲基]-3-(氯苯基)-吡咯烷-2,5-二酮10-23的新曼尼希碱，并评估了它们的最大抗惊厥活性电击 (MES) 和皮下戊四唑 (scPTZ) 癫痫阈值测试。它们的神经毒性是使用旋转棒筛来确定的。几种分子显示出有希望的抗惊厥特性，尤其是在 MES 测试中。在这个癫痫模型中，最活跃的是 N - [4- (4 - 氯苯基) -哌嗪 - 1 - 基} -甲基] -3- (3 - 氯苯基) -吡咯烷 - 2,5 - 二酮 16 和 N - [4-(3-三氟甲基苯基)-哌嗪-1-基}-甲基]-3-(3-氯苯基)-吡咯烷-2,5-二酮17，ED50值为21.4mg/kg和28.83mg /公斤，分别。选定的衍生品 10, 14, 和 16 人在精神运动性癫痫 6-Hz 测试中进行了测试，其中 N - [4- (2 - 氯苯基) -哌嗪 - 1 - 基}
• Selective and tunable synthesis of 3-arylsuccinimides and 3-arylmaleimides from arenediazonium tetrafluoroborates and maleimides
  作者：Zhen-Hua Yang、Zhong-Hui Chen、Yu-Long An、Sheng-Yin Zhao

  DOI：10.1039/c6ra00136j

  日期：——

  arenediazonium tetrafluoroborates and maleimides in the presence of TiCl3. The reactions generated 3-arylsuccinimides in satisfactory yields under mild reaction conditions. In addition, 3-arylmaleimides were obtained by the coupling of arenediazonium tetrafluoroborate and maleimides catalyzed by CuCl. This methodology provided the selective and tunable synthesis of two classes of products by simply

  用于合成3- arylsuccinimides A高效合成策略已经从芳基重氮四氟硼酸盐和马来酰亚胺开发的TiCl的存在3。在温和的反应条件下，反应以令人满意的产率产生了3-芳基琥珀酰亚胺。另外，通过四氟硼酸壬二唑鎓与CuCl催化的马来酰亚胺的偶联，获得了3-芳基马来酰亚胺。通过简单地切换不同的金属试剂，该方法提供了两类产品的选择性和可调谐合成。该方法简单，高效，实用。
• Imidized segmented copolymers
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0438240A2

  公开（公告）日：1991-07-24

  Segmented copolymers having one or more olefin polymer segments and one or more imide-containing are useful for the modification of polyolefins, of polar polymers, and of blends thereof. The polymers can be produced by imidisation of corresponding olefin polymer/(meth)acrylate ester polymer segmented polymer, preferably in a devolatilizing extruder, in the presence of ammonia or primary amines so producing a polymer having one or more segments of polymer containing cyclic imide groups.

  具有一个或多个烯烃聚合物段和一个或多个含酰亚胺段的分段共聚物可用于聚烯烃、极性聚合物及其混合物的改性。这种聚合物可以在氨或伯胺存在下，通过相应的烯烃聚合物/（甲基）丙烯酸酯聚合物分段聚合物的酰亚胺化来生产，最好在脱溶剂挤压机中进行，从而生产出具有一个或多个含有环状酰亚胺基团的聚合物段的聚合物。