N-propyl-4-nitro-phthalimide | 98499-71-9

• 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: N-propyl-4-nitro-phthalimide
• 英文别名: 5-nitro-2-propyl-isoindoline-1,3-dione；5-Nitro-2-propyl-isoindolin-1,3-dion；5-nitro-2-propylisoindole-1,3-dione
• CAS: 98499-71-9
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: DIMVLSWEUOUYFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  N-propyl-4-nitro-phthalimide 在 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-amino-N-propyl phthalimide
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and 3D-QASR of N-Pyridylpyrazole Amide Derivatives Containing a Phthalimide as Potential Ryanodine Receptor Activators

  摘要：

  To develop potent and environment-friendly insecticides, novel N-pyridylpyrazole amide derivatives containing a phthalimide were designed and synthesized. The preliminary bioassay results showed that most of the target compounds exhibited good insecticidal activities. For oriental armyworm (Mythimna separata), compounds E5, E29, E30, and E33 displayed higher than 90% lethal rates at 25 mg L-1. In particular, compound E33 displayed 60% mortality at a lower concentration of 6.25 mg L-1. Besides, compound E33 also showed a 30% lethal rate at 5 mg L-1 against diamondback moth (DBM) (Plutella xylostella). Molecular docking between the most active compound E33 and DBM ryanodine receptor (RyR), comparative molecular field analysis (CoMFA), and density functional theory (DFT) calculations were conducted and discussed. Furthermore, according to vitro studies using a calcium imaging technique, compound E33 was a potent novel lead targeting insect RyR.

  DOI：

  10.1021/acs.jafc.2c03971
• 作为产物：
  描述：

  N-丙基酞酰亚胺 在 硫酸 、 potassium nitrate 作用下， 反应 4.0h， 以90%的产率得到N-propyl-4-nitro-phthalimide
  参考文献：
  名称：

  一种N-烷基-4-硝基邻苯二甲酰亚胺的制备方法

  摘要：

  本发明公开了一种N‑烷基‑4‑硝基邻苯二甲酰亚胺的制备方法，包括以下步骤：步骤1)将苯酐、烷基醛、无机胺混合后，在氢气的作用下反应，经降温结晶、干燥后得到N‑烷基邻苯二甲酰亚胺；步骤2)将步骤1)中得到的N‑烷基邻苯二甲酰亚胺进行硝化反应，产物经纯化、干燥后制得所述N‑烷基‑4‑硝基邻苯二甲酰亚胺；其中，步骤1)所述烷基醛优选为碳1‑4的烷基醛。本发明的制备方法具有原料来源广泛，价格低廉，工艺简单易规模化生产等优点。通过一步法合成，反应效率高，装置简单易操作，绿色环保。

  公开号：

  CN113549001A

文献信息

• Process for preparing bis(ether anhydrides) using alkylamine derived
  申请人：General Electric Company

  公开号：US05536846A1

  公开（公告）日：1996-07-16

  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.degree. to 250.degree. 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.

  一种制备双(醚酐)的过程，使用具有低熔点的烷基胺，从而允许用于准备双(醚酐)的新型中间步骤。这些烷基胺具有至少三个碳原子的烷基，并且在常压下沸点在48℃到250℃的范围内。由于使用这些胺，液态烷基胺现在可以在酰亚胺化过程中使用。根据本发明从回收的酰亚胺化产物制备的N-烷基硝基邻酞菁酰可以使用液/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酞菁酰提供了位移反应，现在可以在高固体含量下运行。同样，交换反应可以在更高的固体含量下运行，从而实现比传统工艺更高的效率水平。
• Process for preparing bis (ether anhydrides) using alkylamine derived
  申请人：General Electric Company

  公开号：US06008374A1

  公开（公告）日：1999-12-28

  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.degree. 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.

  一种制备双(醚酐)的方法采用具有低熔点的烷基胺，从而允许新颖的中间步骤用于制备双(醚酐)。这些烷基胺具有含有至少三个碳原子的烷基，并且在大气压下沸点范围为48至250度。由于使用这些胺，液态烷基胺现在可以用于咪唑化过程步骤。根据本发明从所回收的咪唑化产物制备的N-烷基硝基邻酞菁酰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酞菁酰提供了位阻反应，现在可以在高固体含量下运行。同样，交换反应可以在更高的固体含量下运行，从而实现比传统工艺更高的效率水平。
• Process for preparing BIS(ether anhydrides) using alkylamine derived
  申请人：General Electric Co.

  公开号：US05936099A1

  公开（公告）日：1999-08-10

  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.degree. 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.

  一种制备双(醚酐)的方法，采用熔点较低的烷基胺，从而允许新的中间步骤来制备双(醚酐)。这些烷基胺具有至少三个碳原子的烷基基团，其沸点在大气压下在48至250℃的范围内。由于使用这些胺，现在可以在咪唑化过程中使用液态烷基胺。根据本发明从回收的咪唑化产物制备的N-烷基硝基邻苯二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酰亚胺提供了位移反应，现在可以以高固体含量运行。同样，交换反应可以在更高的固体含量下运行，从而实现比传统工艺更高的效率水平。
• Thalidomide derivatives as nanomolar human neutrophil elastase inhibitors: Rational design, synthesis, antiproliferative activity and mechanism of action
  作者：Beata Donarska、Adrianna Sławińska-Brych、Magdalena Mizerska-Kowalska、Barbara Zdzisińska、Wojciech Płaziński、Krzysztof Z. Łączkowski

  DOI：10.1016/j.bioorg.2023.106608

  日期：2023.9

  antiproliferative activity against human T47D (breast carcinoma), RPMI 8226 (multiple myeloma), and A549 (non-small-cell lung carcinoma) revealed that designed compounds were more active compared to thalidomide, pomalidomide and lenalidomide used as the standard drugs. Additionally, the most active compound 4f derived from lenalidomide induces cell cycle arrest at the G2/M phase and apoptosis in T47D cells

  在这里，我们合理设计了一种源自沙利度胺的人中性粒细胞弹性蛋白酶（HNE）抑制剂4a - 4f。HNE抑制测定表明，合成的化合物4a、4b、4e和4f表现出很强的HNE抑制特性，IC 50值为21.78–42.30 nM。化合物4a、4c、4d和4f表现出竞争性作用模式。最有效的化合物4f显示出与西维来司他几乎相同的 HNE 抑制作用。分子对接分析表明，氮杂环丁烷-2,4-二酮基团与以下三种氨基酸：Ser195、Arg217 和 His57 之间发生最强的相互作用。还证明了结合能和实验确定的IC 50值之间的高度相关性。针对人 T47D（乳腺癌）、RPMI 8226（多发性骨髓瘤）和 A549（非小细胞肺癌）的抗增殖活性研究表明，设计的化合物比用作标准药物的沙利度胺、泊马度胺和来那度胺更具活性。此外，源自来那度胺的最具活性的化合物4f会诱导 T47D 细胞的细胞周期停滞在 G2/M 期并导致细胞凋亡。
• Polyphenylene ether containing reactive end groups, process for preparing it and relevant thermoplastic compositions
  申请人：ENICHEM S.p.A.

  公开号：EP0534543A1

  公开（公告）日：1993-03-31

  Polyphenylene ether containing ether end groups of formula: wherein: R₁ is a halogen atom, an alkyl radical, phenyl, alkyloxy or haloalkyloxy; R₂ is hydrogen, a halogen atom, an alkyl radical, phenyl, alkyloxy or haloalkyloxy; X is oxygen or NR₃; and AR is phenylene or an aromatic radical constituted by 2 or 3 condensed rings. The polyphenylene ether of formula (I) is prepared by reacting a salt of the polyphenylene ether with an aromatic nitro-derivative of formula:

  含有式中醚端基的聚苯醚： 其中R₁ 是卤原子、烷基、苯基、烷氧基或卤代烷氧基；R₂ 是氢、卤原子、烷基、苯基、烷氧基或卤代烷氧基；X 是氧或 NR₃；以及 AR 是亚苯基或由 2 或 3 个缩合环构成的芳香基。 式(I)的聚苯醚是通过将聚苯醚的盐与式(I)的芳香族硝基衍生物反应制备的：