N-[2-(N,N-dimethylamino)ethyl]maleimide | 5135-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-[2-(N,N-dimethylamino)ethyl]maleimide
• 英文别名: 1-[2-(N,N-dimethylamino)ethyl]pyrrole-2,5-dione；1-[2-(dimethylamino)ethyl]-2,5-dihydro-1H-pyrrole-2,5-dione；1-[2-(dimethylamino)ethyl]pyrrole-2,5-dione
• CAS: 5135-58-0
• 化学式: C₈H₁₂N₂O₂
• mdl: MFCD11149230
• 分子量: 168.195
• InChiKey: MTEYNFUBAMXQME-UHFFFAOYSA-N

物化性质

• 熔点：
  175-178 °C(Solv: ethanol (64-17-5))
• 沸点：
  261.5±23.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(N,N-dimethylamino)ethyl]maleimide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 135.0h， 生成
  参考文献：
  名称：

  Heteropolymetallic Complexes Linked to a 9,10-Dihydroanthracenyl Frame. Ruthenium as Active Spectator for Palladium Reactivity

  摘要：

  New monometallic Pd(II) (3, 4) and heteropolymetallic Pd(II)/Ru(II) complexes (5, 6) linked to an original 9,10-dihydroanthracenyl pyrrolidine scaffold were synthesized and fully characterized. For monometallic complexes, exo-3 and endo-4 conformers were exclusively obtained from Pd(OAc)(2) and [PdCl2(COD)], respectively. The formation of the sterically hindered endo-4 was justified by the positive noncovalent intramolecular Cl-pi interaction, observed by X-ray diffraction. The reaction of endo-4 with 1 and 2 equiv of [RuCp(NCMe)(3)]PF6 led to complexes 5 and 6, respectively. It is worth noting that lower conversions in the Suzuki-Miyaura coupling were found using 5 and 6 as catalysts, in comparison to those with monometallic palladium complexes. This behavior could be related to the higher stabilization of Pd(II) species for the heteropolymetallic complexes, as proven by electrochemical analyses.

  DOI：

  10.1021/om5001502
• 作为产物：
  描述：

  以 甲苯 为溶剂， 反应 10.0h， 以91%的产率得到N-[2-(N,N-dimethylamino)ethyl]maleimide
  参考文献：
  名称：

  合成功能化碱性马来酰亚胺的有效方法

  摘要：

  提出了一个三步程序，涉及马来酸酐与呋喃的Diels-Alder缩合反应，与适当的二胺反应后形成N-取代的酰亚胺，以及马来碳-碳双键的最终Diels-Alder再生，以实现明确的合成。的ñ取代基本马来酰亚胺。该新方法的特点是反应条件温和，易于操作，收率高且无需额外的催化作用。

  DOI：

  10.1002/jhet.1651

文献信息

• [EN] SEMISYNTHETIC DERIVATIVES OF NYSTATIN A1<br/>[FR] DÉRIVÉS SEMI-SYNTHÉTIQUES DE NYSTATINE A1
  申请人：BLIRT S A

  公开号：WO2013132014A1

  公开（公告）日：2013-09-12

  The invention provides semisynthetic derivatives of Nystatin A1, water soluble salts and complexes, pharmaceutical compositions and plant protection products comprising the derivatives and their use, as antifungal antibiotics (Formula 1a).

  该发明提供了Nystatin A1的半合成衍生物，水溶性盐和络合物，包括这些衍生物的药物组合物和植物保护产品，以及它们作为抗真菌抗生素的用途（公式1a）。
• Thebaine Adducts with Maleimides. Synthesis and Transformations
  作者：E.E. Shults、M.M. Shakirov、G.A. Tolstikov、V.N. Kalinin、G. Schmidhammer

  DOI：10.1007/s11178-005-0306-8

  日期：2005.8

  Diels-Alder reaction of thebaine with maleimides is structurally specific and yields [7,8,3′,4′ ]-succinimido-endo-ethenotetrahydrothebaines containing N′-alkyl, cycloalkyl, aralkyl or aryl substituents. N′-[1(S)-hydroxymethyl-2-methylpropyl]-succinimido-6,14-endo-ethenotetrahydrothebaine formed in reaction of S-valinol with (7α,8α)-anhydrido-6,14-endo-ethenotetrahydrothebaine. The reduction of the adducts by LiAlH4 afforded N′-substituted 7,8-pyrrolidino-endo-ethenotetrahydrothebaines. The reduction of fused succinimides by NaBH4 resulted in the corresponding 2′α-hydroxylactam derivatives. O-Demethylation of the tetrahydrothebaine pyrrolidine derivatives effected by BBr3 afforded compounds of the tetrahydrooripavine series. The O-demethylation of tetrahydrothebaine succinimide derivatives gave rise to the corresponding 6-demethyl-endo-ethenotetrahydrooripavines. Alkylation conditions were found for N′-(4-hydroxyphenethyl)-substituted tetrahydrothebaine succinimide derivatives.

  霹雳-阿尔德反应中，神仙草碱与马来酰亚胺反应具有结构特异性，生成含有N′-烷基、环烷基、芳基或者芳香烷基取代基的[7,8,3′,4′]-琥珀酰亚胺-内-乙烯四氢神仙草碱。在S-巴醇与(7α,8α)-无水-内-乙烯四氢神仙草碱反应中，形成了N′-[1(S)-羟甲基-2-甲基丙基]-琥珀酰亚胺-6,14-内-乙烯四氢神仙草碱。利用LiAlH4还原加成物得到N′-取代的7,8-吡咯烷基-内-乙烯四氢神仙草碱。用NaBH4还原融合琥珀酰亚胺得到了相应的2′α-羟基内酰胺衍生物。用BBr3对四氢神仙草碱吡咯烷衍生物进行O-去甲基化，得到四氢奥利帕韦系列化合物。四氢神仙草碱有关的琥珀酰亚胺衍生物的O-去甲基化生成对应的6-去甲基-内-乙烯四氢奥利帕韦。对N′-(4-羟基苯乙基)取代的四氢神仙草碱琥珀酰亚胺衍生物进行了烷基化条件的研究。
• Chemical reactivity and antimicrobial activity of <i>N</i>-substituted maleimides
  作者：Natalia Salewska、Joanna Boros-Majewska、Izabela Łącka、Katarzyna Chylińska、Michał Sabisz、Sławomir Milewski、Maria J. Milewska

  DOI：10.3109/14756366.2011.580455

  日期：2012.2.1

  µg ml(-1). Low antimicrobial but high cytostatic activity was noted for basic maleimides containing tertiary aminoalkyl substituents. Chemical reactivity and lipophilicity influenced antibacterial activity of neutral maleimides but had little if any effect on their antifungal and cytostatic action. N-substituted maleimides affected biosynthesis of chitin and β(1,3)glucan, components of the fungal cell

  合成了几种含有具有变化的体积和极性的取代基的N-取代的马来酰亚胺，并测试了其抗微生物和细胞抑制活性。中性马来酰亚胺显示相对较强的抗真菌作用的最小抑制浓度（MIC在0.5-4 µg ml（-1）范围内）；它们的抗菌活性是结构依赖性的，并且都具有高度的细胞抑制作用，IC（50）值低于0.1 µg ml（-1）。对于含有叔氨基烷基取代基的碱性马来酰亚胺，抗菌性低，但具有较高的细胞抑制活性。化学反应性和亲脂性影响中性马来酰亚胺的抗菌活性，但对其抗真菌和细胞抑制作用几乎没有影响。N-取代的马来酰亚胺影响几丁质和β（1,3）葡聚糖，真菌细胞壁的组成部分的生物合成。膜酶β（1
• SEMISYNTHETIC DERIVATIVES OF NYSTATIN A1
  申请人：BLIRT S.A.

  公开号：US20150045316A1

  公开（公告）日：2015-02-12

  The invention provides semisynthetic derivatives of Nystatin A 1 , water soluble salts and complexes, pharmaceutical compositions and plant protection products comprising the derivatives and their use, as antifungal antibiotics (Formula 1a).

  这项发明提供了Nystatin A1的半合成衍生物，水溶性盐和络合物，包括这些衍生物的药物组合物和植物保护产品，以及它们作为抗真菌抗生素的用途（公式1a）。
• Modified cis-1,4-polyisoprene rubber, a process for its manufacture, a vulcanized modified cis-1,4-polyisoprene rubber composition and the use of the modified cis-1,4-polyisoprene rubber for preparing vulcanized shaped articles
  申请人：KURARAY CO., LTD.

  公开号：EP0066241A2

  公开（公告）日：1982-12-08

  Described is a modified cis-1,4-polyisoprene rubber on the basis of a solid synthetic cis-1,4-polyisoprene containing in its molecule per 100 repeating isoprene units at least 0.01 mole of a succinimide derivative of the general formula I wherein R1 is hydrogen or a covalent bond with the rubber molecule, R2 is a hydrocarbon residue having not more than 20 carbon atoms, and optionally containing an oxygen or sulfur atom in its principal chain, and A is a dihydrocarbylamino residue having not more than 20 carbon atoms, and containing at least one tertiary nitrogen atom as a hetero atom. This modified rubber exhibits excellent green strength at room temperature and flowability at elevated temperatures. In its vulcanized form it is comparable to, or better than vulcanized natural rubber in tensile strength and hardness.

  所述改性顺式-1,4-聚异戊二烯橡胶以固体合成顺式-1,4-聚异戊二烯为基础，其分子中每 100 个重复异戊二烯单元至少含有 0.01 摩尔通式 I 的琥珀酰亚胺衍生物。 其中 R1 是氢或与橡胶分子之间的共价键；R2 是碳原子数不超过 20 个的烃残基，其主链中可选择含有一个氧原子或硫原子；A 是碳原子数不超过 20 个的二氢羰基氨基残基，其杂质原子中至少含有一个叔氮原子。这种改性橡胶在室温下具有优异的生坯强度，在高温下具有良好的流动性。在硫化状态下，其拉伸强度和硬度与硫化天然橡胶相当，甚至更好。