5-(4-(cyano)benzylamino)-5-oxopentanoic acid | 946852-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-(cyano)benzylamino)-5-oxopentanoic acid
• 英文别名: 5-(4-(Cyano) benzylamino)-5-oxopentanoic acid；5-[(4-cyanophenyl)methylamino]-5-oxopentanoic acid
• CAS: 946852-96-6
• 化学式: C₁₃H₁₄N₂O₃
• mdl: MFCD12832119
• 分子量: 246.266
• InChiKey: QYGOMCJYDPYHJV-UHFFFAOYSA-N

物化性质

• 沸点：
  577.8±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-(cyano)benzylamino)-5-oxopentanoic acid 在 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  从DNA编码的化学文库中分离高亲和力胰蛋白酶抑制剂。

  摘要：

  DOI：

  10.1002/anie.200700654
• 作为产物：
  描述：

  戊二酸酐 、 4-(氨甲基)苯腈盐酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以93%的产率得到5-(4-(cyano)benzylamino)-5-oxopentanoic acid
  参考文献：
  名称：

  Interfacial tetrazine click chemistry mediated assembly of multifunctional colloidosomes

  摘要：

  我们提出了一种简便的方法，通过四唑点击化学反应，实现金纳米颗粒基胶囊的快速和自主界面交联。

  DOI：

  10.1039/d1cc03886a

文献信息

• 다공성 알지네이트 기반 하이드로겔, 이의 제조방법 및 이를 이용한 약물 전달체
  申请人：부경대학교 산학협력단

  公开号：KR20220007476A

  公开（公告）日：2022-01-18

  본 발명은 다공성 알지네이트 기반 하이드로겔, 이의 제조방법 및 이를 이용한 약물 전달체에 관한 것으로, 본 발명에 따른 다공성 하이드로겔은, 고분자 매트릭스 재료 및 가교제에 각각 도입되어 있는 서로 클릭반응 가능한 작용기에서 클릭반응시 N 2 가스가 발생함에 따라 하이드로겔에 다공성을 부여함을 특징으로 하고, 이에 따른 다공성은 약물 방출을 유도하는 약물전달체로서 초기의 급격한 약물방출이 억제되고 서방형 약물 방출 특징을 가져 제약분야와 화장품 분야에 유용하게 사용할 수 있다.

  本发明涉及基于多孔性海藻酸盐的水凝胶、其制备方法以及用于药物传递的药物载体。根据本发明，多孔性水凝胶具有多孔性，当在具有可点击反应作用基团的高分子基质材料和交联剂中引入时，由于点击反应而产生N2气体，从而赋予水凝胶多孔性。由此产生的多孔性可用作药物释放的药物载体，具有抑制初始剧烈药物释放和缓慢、持续药物释放的特点，可在制药和化妆品领域中有用。
• An efficient metal catalyst free approach to synthesize 5-(4-(1,2,4,5 tetrazin-3-yl)benzylamino)-5-oxopentanoic acid
  作者：Berhanu Zewde、Olufolasade Atoyebi、Dharmaraj Raghavan

  DOI：10.1016/j.tetlet.2018.06.071

  日期：2018.8

  Despite the wide use of 1,2,4,5-tetrazines in biomaterials and materials science, currently there does not exist synthetic method(s) that can yield significant amount of 1,2,4,5- tetrazines without the use of potentially toxic metal catalysts. Here, we report a less energy intensive and more efficient metal catalyst free approach for the synthesis of an asymmetric tetrazine. A range of operating parameters such as extraction pH and temperature were regulated to achieve a practical yield nearly 1.5 times greater than the yields reported in the literature for similar synthetic procedures. (C) 2018 Elsevier Ltd. All rights reserved.
• Synthetically Tractable Click Hydrogels for Three-Dimensional Cell Culture Formed Using Tetrazine–Norbornene Chemistry
  作者：Daniel L. Alge、Malar A. Azagarsamy、Dillon F. Donohue、Kristi S. Anseth

  DOI：10.1021/bm4000508

  日期：2013.4.8

  The implementation of bio-orthogonal click chemistries is a topic of growing importance in the field of biomaterials, as it is enabling the development of increasingly A complex hydrogel materials capable of providing dynamic, cell-instructive microenvironments. Here, we introduce the tetrazine norbornene inverse electron demand Diels-Alder reaction as a new cross-linking chemistry for the formation of cell laden hydrogels. The fast reaction rate and irreversible nature of this click reaction allowed for hydrogel formation within minutes when a multifunctional PEG-tetrazine macromer was reacted with a dinorbomene peptide. In addition, the cytocompatibility of the polymerization led to high postencapsulation viability of human mesenchymal stem cells, and the specificity of the tetrazine norbornene reaction was exploited for sequential modification of the network via thiol-ene photochemistry. These advantages, combined with the synthetic accessibility of the tetrazine molecule compared to other bio-orthogonal click reagents, make this cross-linking chemistry an interesting and powerful new tool for the development of cell-instructive hydrogels for tissue engineering applications.
• Facile and efficient Lewis acid catalyzed synthesis of an asymmetric tetrazine useful for bio-orthogonal click chemistry applications
  作者：Daniel L. Alge、Dillon F. Donohue、Kristi S. Anseth

  DOI：10.1016/j.tetlet.2013.08.010

  日期：2013.10

  Bio-orthogonal tetrazine click reactions have recently attracted significant interest for applications spanning biological imaging, cancer targeting, and biomaterials science. Here, we report a simple and efficient two-step scheme for the synthesis of an asymmetric tetrazine molecule containing a carboxylic acid handle for subsequent macromolecular conjugation. Yields as high as 75% were achieved using as little as 0.005 equiv of nickel triflate catalyst, which is a significant improvement over previous methodologies. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.