2-(4-nitrobutyl)-1H-isoindole-1,3(2H)-dione | 2518-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(4-nitrobutyl)-1H-isoindole-1,3(2H)-dione
• 英文别名: 1-Phthalimido-4-nitrobutan；N-(4-nitro-butyl)-phthalimide；4-nitro-N-butylphthalimide；2-(4-nitrobutyl)isoindole-1,3-dione
• CAS: 2518-82-3
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: FKKOQCKFOUFYSF-UHFFFAOYSA-N

物化性质

• 熔点：
  69-72 °C
• 沸点：
  415.0±28.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-nitrobutyl)-1H-isoindole-1,3(2H)-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 1-Amino-4-nitro-butan
  参考文献：
  名称：

  Stoffwechselprodukte von Mikroorganismen 49. Mitteilung. Die Ferrioxamine A1, A2 und D2

  摘要：

  AbstractThe structures of the ferrioxamines A1, A2, and D2, minor components of the sideramine mixtures from cultures of Streptomyces, have been determined by degradation and, in part, by synthesis. Whereas the previously investigated ferrioxamines B, D1, E, and G contain but a single basic component, 1‐amino‐5‐hydroxylaminopentane, the ferrioxamines A1, A2, and D2 contain in addition to this base its lower homologue, 1‐amino‐4‐hydroxylamino‐butane.

  DOI：

  10.1002/hlca.19650480407
• 作为产物：
  描述：

  2-(4-碘丁基)异吲哚-1,3-二酮 在 silver(I) nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以84%的产率得到2-(4-nitrobutyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  水性介质下伯烷基卤首次转化为硝基烷

  摘要：

  通过使相应的卤代衍生物与亚硝酸银反应，可以很容易地在水性介质中获得伯硝基烷和α，ω-二硝基烷。该方法对于烷基溴化物和烷基碘化物都很好地工作，并且即使在存在其他官能团的情况下也以令人满意的良好收率进行，从而最小化了不希望的亚硝酸烷基酯的形成。

  DOI：

  10.1021/jo049048b

文献信息

• One-pot cascade synthesis of azabicycles <i>via</i> the nitro-Mannich reaction and <i>N</i>-alkylation
  作者：Wannaporn Disadee、Somsak Ruchirawat

  DOI：10.1039/c7ob03104a

  日期：——

  A one-pot, metal-free process for the synthesis of azabicycles is developed. The key transformations involved a cascade of double intramolecular cyclizations via the nitro-Mannich reaction and N-alkylation, providing various ring systems of azabicycles in yields up to 81% and an isomeric ratio of 62 : 1. This approach offers considerable advantages in terms of the handling of small molecules, the flexibility

  开发了一种单锅，无金属的合成氮杂双环化合物的方法。关键的转化涉及通过硝基-曼尼希反应和N-烷基化进行的一系列双分子内环化反应，提供了各种氮杂双环系统，产率高达81％，异构体比率为62：1。小分子的处理，引入功能化侧链的灵活性以及直接进入各种氮杂双环的途径。
• PRODUCTION OF LOW COLOR POLYETHERIMIDES
  申请人：GUGGENHEIM THOMAS Link

  公开号：US20090292128A1

  公开（公告）日：2009-11-26

  The production of low color polyetherimides, including its intermediates, such as bisimides and diaryl diether dianhydrides, may be affected by producing an improved purity intermediate of 4-nitro-N-alkylphthalimide. A salt, such as alkali metal carbonate or alkali metal hydrogen carbonate, is added to an aqueous mixture of 4-nitro-N-alkylphthalimide and 3-nitro-N-alkylphthalimide to selectively hydrolyze the imide linkage of 3-nitro-N-alkylphthalimide forming a water-soluble acid-amide salt. An organic solvent is added to this salt mixture to phase separate 4-nitro-N-alkylphthalimide having dissolved in the organic solvent from acid-amide salt of 3-nitro-N-alkylphthalimide having dissolved in water.

  生产低色差聚醚酰亚胺，包括其中间体，如双亚酰亚胺和二芳基二醚二酐，可能会受到生产改进纯度的4-硝基-N-烷基邻苯二甲酰亚胺中间体的影响。将盐，如碱金属碳酸盐或碱金属氢碳酸盐，加入到4-硝基-N-烷基邻苯二甲酰亚胺和3-硝基-N-烷基邻苯二甲酰亚胺的水溶混合物中，选择性水解3-硝基-N-烷基邻苯二甲酰亚胺的亚醯胺键，形成水溶性酸酰胺盐。然后向这个盐混合物中加入有机溶剂，将溶解在有机溶剂中的4-硝基-N-烷基邻苯二甲酰亚胺与溶解在水中的3-硝基-N-烷基邻苯二甲酰亚胺的酸酰胺盐进行相分离。
• Process for preparing bis(ether anhydrides)
  申请人：GENERAL ELECTRIC COMPANY

  公开号：EP0684232A1

  公开（公告）日：1995-11-29

  A process for making bis(ether anhydrides) employs alkylamines having low melting temperatures thus allowing for novel intermediate process steps for preparing bis(ether anhydrides). The alkylamines have alkyl groups which contain at least three carbon atoms and have boiling temperatures in the range of 48 to 250°C at atmospheric pressure. As a result of using these amines, liquid alkylamines now can be employed in the imidization process step. The N-alkyl nitrophthalimides prepared from the recovered imidization product according to this invention can now be purified using liquid/liquid extraction or vacuum distillation. The alkyl nitrophthalimides prepared according to this invention provide for displacement reactions which now can be run at a high solids level. Likewise, the exchange reaction can be run at a higher solids level, and thus achieves an efficiency level which is higher than conventional processes.

  一种制造双（醚酐）的工艺采用了具有低熔点的烷基胺，从而实现了制备双（醚酐）的新型中间工艺步骤。这些烷基胺具有至少含有三个碳原子的烷基，在常压下的沸点范围为 48 至 250°C。由于使用了这些胺，现在可以在亚胺化工艺步骤中使用液态烷基胺。根据本发明，从回收的亚胺化产物中制备的 N-烷基硝基邻苯二甲酰亚胺现在可以使用液/液萃取或真空蒸馏进行纯化。根据本发明制备的烷基硝基邻苯二甲酰亚胺可用于置换反应，该反应现在可以在高固体水平下进行。同样，置换反应也可以在较高的固体含量下进行，从而达到比传统工艺更高的效率水平。
• Chemoselective SN2′ reaction of nitroalkanes to dialkyl 2-(bromomethyl)fumarates under cetyltrimethylammonium hydroxide (CTAOH) catalysis
  作者：Roberto Ballini、Serena Gabrielli、Alessandro Palmieri

  DOI：10.1016/j.tetlet.2009.12.122

  日期：2010.2

  The chemoselective S(N)2' reaction of a variety of primary nitroalkanes to dialkyl 2-(bromomethyl)fumarates can be efficiently performed under cetyltrimethylammonium hydroxide (CTAOH) catalysis. The alpha, beta-unsaturated esters were obtained in satisfactory to good yields with the complete retention of the nitro group. (C) 2009 Elsevier Ltd. All rights reserved.
• PROCESS FOR THE PREPARATION OF N-METHYL-D-PHENYLALANYL-N- 1- 3- (AMINOIMINOMETHYL)AMINO]PROPYL]-3,3-DIFLUORO-2-OXOHEXYL]-L-PROLINAMIDE
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP1012165A1

  公开（公告）日：2000-06-28