N-cyanomaleimide | 135205-68-4

• 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-cyanomaleimide
• 英文别名: cyanomaleimide；1H-Pyrrole-1-carbonitrile,2,5-dihydro-2,5-dioxo-(9CI)；2,5-dioxopyrrole-1-carbonitrile
• CAS: 135205-68-4
• 化学式: C₅H₂N₂O₂
• mdl: MFCD18810073
• 分子量: 122.083
• InChiKey: OMNMBDWTNMSXKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  亚硝基叔丁烷 、 N-cyanomaleimide 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Spin Adducts from the Reaction Between N-Phenyl-alpha-tert-butylnitrone (PBN) and Activated Olefins. A Facile Pathway Converting PBN into 2-Methyl-2-nitrosopropane (MNP).

  摘要：

  N-Phenyl-alpha-tert-butylnitrone (PBN) reacts with activated olefins RCH=CHR, such as maleimides, maleic anhydride or diethyl maleate, with formation of two types of persistent spin adducts giving characteristic EPR spectra, denoted types A and B. Spin adducts with type A spectrum were formed photochemically and identified as reductive coupling products between the olefin and PEN, RCH2CH(R)-PBN.. Spin adducts with type B spectra were formed photochemically and/or thermally and were identified as reductive coupling products RCH2CH(R)-N(O-.)Bu-t between the olefin and a degradation product of PEN, 2-methyl-2-nitrosopropane (MNP, t-BuNO).The conversion of PEN to t-BuNO was studied for a compound with an exceedingly reactive nitrogen-nitrogen double-bond, namely 4-phenyl-4H-1,2,4-triazoline-3,5-dione (PTAD). In this case, a 74% yield of t-BuNO was obtained in a short period of time; alpha,N-diphenylnitrone reacted similarly to give nitrosobenzene. The reaction between PEN and an activated olefin was assumed to occur analogously, either via the initial formation of a 1,3-dipolar cycloadduct or some parallel reaction involving attack of the electrophilic olefin at the PEN a-carbon. The 1,3-dipolar cycloadduct between PEN and N-phenylmaleimide exhibited favourable initiator properties for living polymerization of styrene.A new type of spin adduct, RCH(Bu-t)CH(R)-N(O-.)Bu-t, was prepared by the photochemical reaction between an activated olefin and t-BuNO. This reaction presumably proceeds by photocleavage of t-BuNO to NO and t-Bu-., the latter reacting with the activated olefin to give a transient radical, RCH(Bu-t)CH.(R), which is trapped by t-BuNO.

  DOI：

  10.3891/acta.chem.scand.52-1081
• 作为产物：
  描述：

  马来酰亚胺 、 溴化氰 生成 N-cyanomaleimide
  参考文献：
  名称：

  Trapping of the Cyano Radical: Does it Ever Happen?

  摘要：

  The possible trapping of the cyano radical by alpha-phenyl-N-tert-butylnitrone (PBN) has been probed by a new method Tor the generation of CN., photolysis of N-cyanosuccinimide with PBN. Only in 1,1,1,3,3,3-hexafluoroprppan-2-ol was EPR spectral evidence obtained for the formation of a true spin adduct, namely the isocyano adduct of PBN. In other solvents, like dichloromethane or acetonitrile. the photolysis reaction took an entirely different course and gave the N-cyano-3-succinimidyl adduct of PBN and a second aminoxyl of unknown structure. The same pair of adducts could be obtained by photolysis of N-cyanomaleimide and PBN in a reductive coupling reaction. Maleimide gave a similar but clearly different pair of spectra.The possibility that the cyano or isocyano PBN adduct might undergo spontaneous hydrolysis to give the aminoformyl or formylamino adduct, respectively, was explored. It was shown that the authentic cyano adduct does not give the aminoformyl adduct under hydrolytic conditions. Since there is no method to prepare the isocyano adduct for such experiments, the problem of its hydrolytic reactivity is still open. The aminoformyl adduct of PBN was prepared by addition of the formamide anion to PBN, followed by oxidation by nickel peroxide, and characterized by its EPR spectrum.

  DOI：

  10.3891/acta.chem.scand.52-0608

文献信息

• Substituted 2-amino-5-maleimido thiophenes and substituted
  申请人：Eastman Kodak Company

  公开号：US05179207A1

  公开（公告）日：1993-01-12

  Provided are certain substituted 2-aminothiazoles and 2-aminothiophenes which are useful as red colorants and as intermediates in the synthesis of bathochromic azo dyes. These compounds are prepared by reacting 2-aminothiophenes or 2-aminothiazoles, which contain a primary amino group, with 2-chloro-3-negatively-substituted maleimides. These compounds can be diazotized and coupled with azo components, for example, anilines, 1,2,3,4-tetrahydroquinolines, 2,3-dihydroindoles, and 3,4-dihydro-2H-1,4-benzoxazines to form bathochromic blue-cyan azo dyes.

  提供了一些替代的2-氨基噻唑和2-氨基噻吩，它们可用作红色染料，并用作合成巴托克罗米克偶氮染料的中间体。这些化合物是通过将含有一级氨基的2-氨基噻吩或2-氨基噻唑与2-氯-3-负取代马来酰亚胺反应制备而成。这些化合物可以重氮化并与偶氮组分偶联，例如苯胺，1,2,3,4-四氢喹啉，2,3-二氢吲哚和3,4-二氢-2H-1,4-苯并噁唑，形成巴托克罗米克蓝-青色偶氮染料。