tris(2-isocyanoethyl)amine | 208247-83-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tris(2-isocyanoethyl)amine
• 英文别名: 2-isocyano-N,N-bis(2-isocyanoethyl)ethanamine
• CAS: 208247-83-0
• 化学式: C₉H₁₂N₄
• 分子量: 176.221
• InChiKey: DKFBZIIJBPFCKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  16.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-(4-nitrophenyl)-2-thioethane-thioamide 、 tris(2-isocyanoethyl)amine 以 二氯甲烷 为溶剂， 反应 10.0h， 以60%的产率得到tris-(2-aminoethyl)-N,N',N''-tris-[4-(dimethylamino)-5-(4-nitrophenyl)-1,3-dithiol-2-ylidene]amine
  参考文献：
  名称：

  α-硫代硫代酰胺：异氰酸酯和二异氰酸酯的正式[4 + 1]环加成反应及其在新的直接形成的延伸的四硫富瓦烯中的应用

  摘要：

  根据标题方法，在温和的条件下已经制备了许多带有推挽式取代基的2-（烷基亚氨基）和2-（芳基亚氨基）-1,3-二硫醇（氮杂DTF）。这种新颖的策略依赖于这样的事实，即使用共轭二异氰酸酯可以有效合成新的扩展四硫富富瓦烯（TTF）。两个二硫醇部分通过结合了苯基，联苯基或偶氮联苯基的共轭框架连接。为了了解制备的单，双和三（1,3-二硫醇）衍生物的1 H和13 C NMR光谱，需要进行高温和低温测量。还描述了它们的电化学氧化。

  DOI：

  10.1002/1099-0690(200102)2001:4<655::aid-ejoc655>3.0.co;2-a
• 作为产物：
  描述：

  N-{2-[Bis-(2-formylamino-ethyl)-amino]-ethyl}-formamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 16.3h， 以5.83 g的产率得到tris(2-isocyanoethyl)amine
  参考文献：
  名称：

  USE OF METAL SCAVENGERS FOR REMOVAL OF RUTHENIUM RESIDUES

  摘要：

  该发明涉及使用式（1）中所述的金属清除剂，其中变量如发明描述中定义的那样，用于从后反应混合物中去除钌残留物、化合物或其配合物，从使用钌配合物催化的反应产物中去除，以及从受钌污染的有机化合物中去除。

  公开号：

  US20160297742A1

文献信息

• <b>A Multiple Multicomponent Approach to Chimeric Peptide-Peptoid Podands</b>
  作者：Daniel G. Rivera、Fredy León、Odette Concepción、Fidel E. Morales、Ludger A. Wessjohann

  DOI：10.1002/chem.201201591

  日期：2013.5.10

  (pseudo)peptidic receptors, a new approach based on multiple Ugi four‐component reactions (Ugi‐4CR) is proposed as a means of simultaneously incorporating several binding and catalytic elements into organizing scaffolds. By employing α‐amino acids either as the amino or acid components of the Ugi‐4CRs, this multiple multicomponent process allows for the one‐pot assembly of podands bearing chimeric peptide–peptoid

  传统上，多臂，基于肽的受体在超分子化学中的成功不仅取决于序列，而且同样取决于各种肽链的适当定位以创建结合元件的多价阵列。作为对（伪）肽受体的一种更快，更通用和替代的访问方式，提出了一种基于多种Ugi四组分反应（Ugi-4CR）的新方法，作为将几种结合和催化元素同时整合到组织支架中的一种手段。通过使用α-氨基酸作为Ugi-4CRs的氨基酸或酸成分，这种多组分过程允许一锅组装带有嵌合肽-类肽链作为附加臂的豆荚。碗形的三脚架 凹形多功能骨架被用作拓扑上多样化的平台，用于定位由Ugi-4CRs形成的多个肽链。用类似的方法，合成了具有几个轴向异氰酸酯基的甾体结构单元，并利用其将构象约束的嵌合链对齐，从而为经典的肽-甾体受体提供了另一种选择。分支和杂合的肽-类肽附属物为合成受体的合理设计和组合生产提供了新的可能性。该概念也可扩展到其他多组分反应。合成了具有几个轴向异氰酸酯基的甾体结构单元，并利用其将构
• Combinatorial Synthesis of Macrocycles by Multiple Multicomponent Macrocyclization Including Bifunctional Building Blocks (MiB)
  作者：Ludger Wessjohann、Daniel Rivera、Otilie Vercillo

  DOI：10.1055/s-2007-968006

  日期：2007.2

  incorporation of varied building blocks into the resulting macrocycles by mixing all the components in the same reaction pot. Both skeletal and appendage diversity could be generated in one shot due to the multicomponent nature of the system. HPLC and ESI-MS analyses showed a well-distributed composition of the libraries and revealed the presence of all possible macrocycles resulting from the different

  通过将组合原理应用于 MiB 方法，产生了基于 peptoid 的宏（多）循环的小型库。这种组合方法的特点是通过在同一个反应罐中混合所有组分，将不同的结构单元结合到所得的大环中。由于系统的多组分性质，骨骼和附属物的多样性可以在一次射击中产生。HPLC 和 ESI-MS 分析表明文库的组成分布良好，并揭示了所有可能的大环的存在，这些大环是由不同的构建块组合产生的，尤其是具有任何其他一锅法无法获得的差异取代桥的成员。
• A Multidimensional Approach to Modulating Ionizable Lipids for High‐Performing and Organ‐Selective mRNA Delivery
  作者：Zepeng He、Zhicheng Le、Yi Shi、Lixin Liu、Zhijia Liu、Yongming Chen

  DOI：10.1002/anie.202310401

  日期：2023.10.23

  The development of lipid nanoparticles (LNPs) has enabled a successful clinical application of mRNA vaccines. However, disclosure of design principles for the core component‐ionizable lipids (ILs), improving the delivery efficacy and organ targeting of LNPs, remains a formidable challenge. Herein, we report a powerful strategy to modulate ILs in one‐step chemistry using the Ugi four‐component reaction (Ugi‐4CR) under mild conditions. A large IL library of new structures was established simply and efficiently through a multidimensional approach, allowing us to identify the top‐performing ILs in delivering mRNA via the formulated LNPs. Adjusting the skeleton of ILs has transformed the organ‐specific and robust transfection in mRNA delivery from the liver to the spleen following different administration routes. Of note, a series of isomeric ILs were prepared and we found that the isomers mattered greatly in the performance of LNPs for mRNA delivery. Furthermore, owing to the bis‐amide bonds formed in the Ugi‐4CR reaction, the ILs within LNPs may form hydrogen bonding intermolecularly, facilitating the colloidal stabilization of LNPs. This work provides clues to the rapid discovery and rational design of IL candidates, assisting the application of mRNA therapeutics.

  摘要 脂质纳米颗粒（LNPs）的开发使 mRNA 疫苗成功应用于临床。然而，揭示核心成分--可离子化脂质（ILs）的设计原理，提高 LNPs 的递送效力和器官靶向性，仍然是一个艰巨的挑战。在此，我们报告了一种在温和条件下使用 Ugi 四组份反应 (Ugi-4CR) 一步化学法调节 ILs 的强大策略。通过多维方法，我们简单高效地建立了一个包含新结构的大型IL库，从而确定了在通过配制的LNPs递送mRNA方面表现最佳的IL。调整ILs的骨架改变了不同给药途径将mRNA从肝脏传递到脾脏的器官特异性和强转染性。值得注意的是，我们制备了一系列异构体IL，并发现异构体对LNPs递送mRNA的性能有很大影响。此外，由于在 Ugi-4CR 反应中形成了双酰胺键，LNPs 中的 IL 可能会在分子间形成氢键，从而促进 LNPs 的胶体稳定。这项工作为快速发现和合理设计IL候选物提供了线索，有助于mRNA疗法的应用。
• Architectural Chemistry: Synthesis of Topologically Diverse Macromulticycles by Sequential Multiple Multicomponent Macrocyclizations
  作者：Daniel G. Rivera、Ludger A. Wessjohann

  DOI：10.1021/ja809005k

  日期：2009.3.18

  How can conformationally restricted polyvalent molecules be accessed rapidly? A sequential approach involving two multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) with up to five Ugi-four-component reactions (Ugi-4CR) has been developed to produce nonsymmetric macromulticycles. Topologically diverse structures, such as nonsymmetric cryptands and clam-,and igloo-shaped macromulticycles were obtained in reaction sequences that comprise the incorporation of up to 13 building blocks by forming 20 new bonds without purification of intermediates. Cryptands were produced by a sequential-MiB procedure in which the Ugi-type functional groups of the second MiB are attached to the peptoid backbones from the first multicomponent macrocyclization. These macrobicycles show two completely new features; i.e., three different tether chains can be obtained in one pot, and tertiary amide bonds are used as bridgeheads. Alternatively, the same reaction sequence, i.e., MiB/deprotection/MiB, can be used to produce clam-shaped macrobicycles, demonstrated with a tetrafunctional cholanic steroid as a hinge moiety. Macrotetracycles endowed with igloo-type topologies are accessible by an advanced protocol featuring consecutive double and 3-fold Ugi-4CR-based macrocyclizations. Other building blocks than cholanic steroids employed include aryl, heterocyclic, polyether, and other recognition motifs. The examples given are a first-generation demonstration of an "architectural chemistry" that allows to construct three-dimensional multimotif covalent molecular "buildings" of unprecedented complexity by design.
• Supramolecular Compounds from Multiple Ugi Multicomponent Macrocyclizations:  Peptoid-based Cryptands, Cages, and Cryptophanes
  作者：Daniel G. Rivera、Ludger A. Wessjohann

  DOI：10.1021/ja060720r

  日期：2006.6.1

  The first 3-fold multicomponent macrocyclizations of trifunctional building blocks were developed to produce, in one pot, cryptands, cages, and cryptophanes with peptoid tethers carrying additional recognition motifs. The straightforward, efficient, and diversity-oriented fashion by which these complex macromulticycles are obtained is suitable for building combinatorial libraries of synthetic receptors with potential applicability in catalysis and supramolecular and coordination chemistry. The strategy also easily allows creation of asymmetric macromulticyclic cavities, with up to 20 new bonds formed in one pot.