1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene | 828931-45-9

• 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: 1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene
• 英文别名: 1,3,5-Tris(phthalimidomethyl)-2,4,6-triethylbenzene；2-[[3,5-bis[(1,3-dioxoisoindol-2-yl)methyl]-2,4,6-triethylphenyl]methyl]isoindole-1,3-dione
• CAS: 828931-45-9
• 化学式: C₃₉H₃₃N₃O₆
• 分子量: 639.708
• InChiKey: VZXZBXBOHDHNBA-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238 °C
• 沸点：
  772.0±60.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene 在 hydrazine hydrate 、 potassium hydroxide 作用下， 以 乙醇 、 甲苯 、 水 为溶剂， 反应 20.0h， 以79%的产率得到1,3,5-三(氨基甲基)-2,4,6-三乙基苯
  参考文献：
  名称：

  具有截断四面体几何形状的形状持久 [4+4] 亚胺笼。

  摘要：

  形状持久性有机笼化合物的合成通常基于使用容易获得的前体的多重动态共价键形成（例如亚胺）。通过仔细选择前体几何形状，可以准确设计所得笼的几何形状和尺寸，并且实际上迄今为止已经实现了许多不同的几何形状和尺寸。尽管如此，人们对反应官能团的前体构象刚性和空间预组织对反应结果的影响知之甚少。在此，讨论了前体中构象刚性对具有截断四面体几何形状的 [4+4] 亚胺笼形成的影响。

  DOI：

  10.1002/chem.201705713
• 作为产物：
  描述：

  1,3,5-三乙基苯 在 氢溴酸 、 zinc dibromide 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene
  参考文献：
  名称：

  具有截断四面体几何形状的形状持久 [4+4] 亚胺笼。

  摘要：

  形状持久性有机笼化合物的合成通常基于使用容易获得的前体的多重动态共价键形成（例如亚胺）。通过仔细选择前体几何形状，可以准确设计所得笼的几何形状和尺寸，并且实际上迄今为止已经实现了许多不同的几何形状和尺寸。尽管如此，人们对反应官能团的前体构象刚性和空间预组织对反应结果的影响知之甚少。在此，讨论了前体中构象刚性对具有截断四面体几何形状的 [4+4] 亚胺笼形成的影响。

  DOI：

  10.1002/chem.201705713

文献信息

• Compounds Combining a Macrocyclic Building Block and Flexible Side‐Arms as Carbohydrate Receptors: Syntheses and Structure‐Binding Activity Relationship Studies
  作者：Felix Amrhein、Monika Mazik

  DOI：10.1002/ejoc.202100758

  日期：2021.12.14

  Structure-binding activity relationship studies with compounds consisting of a macrocyclic building block and flexible side-arms revealed the essential role of the side-arms in achieving strong complexation of all-equatorial substituted sugars, such as β-D-glucopyranoside.

  用由大环结构单元和柔性侧臂组成的化合物的结构结合活性关系研究揭示了侧臂在实现全赤道取代糖（如 β-D-吡喃葡萄糖苷）的强复合中的重要作用。
• 8-Hydroxyquinoline as a building block for artificial receptors: binding preferences in the recognition of glycopyranosides
  作者：Monika Mazik、Christoph Geffert

  DOI：10.1039/c0ob00960a

  日期：——

  the recognition of glycosides. Compared to the previously described three-armed aminopyridine-based receptor, compounds 1 and 2 showed significantly increased affinity to β-galactoside. Receptor 2, incorporating two 8-hydroxyquinoline units, was shown to be the most effective receptor for β-galactoside. Compound 3, bearing one 8-hydroxyquinoline group, was found to be a highly effective receptor for

  8-羟基喹啉含三取代三乙苯核心的基于1-3的受体被制备，并评估了它们与糖苷的结合特性。1 H NMR和荧光滴定以及结合研究在两相系统中，如非极性介质，并从含水糖相转移到有机溶剂中的固体碳水化合物的溶解，表明β-相对于在识别α端基异构体的结合偏好苷。与之前描述的三臂相比氨基吡啶基受体，化合物1倍2显示对β-D-半乳糖苷显著增加的亲和力。受体2，包含两个8-羟基喹啉单位被证明是β-半乳糖苷最有效的受体。化合物3，带有一个8-羟基喹啉发现该基团是β-葡萄糖苷的高效受体，并且显示出比基于喹啉的化合物4更有效的受体，表明喹啉羟基在络合物形成中的重要作用。
• Hydrogen and Halogen Bonding in the Crystal Structure of a 1,3,5-Substituted 2,4,6-Triethylbenzene Consisting of Three Phenanthroline Units
  作者：Monika Mazik、Andrè Hartmann、Peter G. Jones

  DOI：10.1002/ejoc.200900811

  日期：2010.1

  6-triethylbenzene (1) was synthesized and its crystal structure was examined. X-ray structural analysis revealed the presence of hydrogen-bonded water molecules as well as hydrogen- and halogen-bonded chloroform molecules in the crystal structure of 1. The 1·H 2 O·CHCl 3 associate is stabilized by N―H···O, O―H···N, O―H···O, C―H···O, and C―H···Cl hydrogen bonds as well as C―Cl···O, C―Cl···π, and C―Cl···Cl

  合成了 1,3, 5-Tris-[N-( 1,10-phenanthrolin-2-yl-carbonyl) 氨基甲基]-2,4,6-三乙苯 (1) 并研究了其晶体结构。X 射线结构分析表明在 1 的晶体结构中存在氢键水分子以及氢键和卤素键的氯仿分子。1·H 2 O·CHCl 3 缔合物被 N-H··稳定·O、O―H···N、O―H···O、C―H···O、C―H···Cl氢键以及C―Cl···O、C― Cl…π, 和 C―Cl…Cl 相互作用。在晶体结构中观察到特别短的 C-H...O 氢键，H...O 和 C...O 的距离分别为 1.89 和 2.94 A。H···O 距离比相关原子的范德华半径之和短约 30%。
• A New Tripodal Receptor for Molecular Recognition of Monosaccharides. A Paradigm for Assessing Glycoside Binding Affinities and Selectivities by ¹H NMR Spectroscopy
  作者：Alberto Vacca、Cristina Nativi、Martina Cacciarini、Roberto Pergoli、Stefano Roelens

  DOI：10.1021/ja045813s

  日期：2004.12.1

  A new tripodal receptor for the recognition of monosaccharides is described. The prototypical host 1 features a 1,35-substituted 2,4,6-tri ethyl benzene scaffold bearing three convergent H-bonding units. The binding ability of the t-octyl derivative la toward a set of octylglycosides of biologically relevant monosaccharides, including Glc, Gal, Man, and GlcNAc, was investigated by H-1 NMR in CDCl3. A protocol for the correct evaluation of binding affinities was established, which can be generally applied for the recognition of monosaccharides by H-1 NMR spectroscopy. A three-constant equilibrium model, including 1:1 and 2:1 host-guest association and dimerization of the receptor, was ascertained for the interaction of la with all the investigated glycosides. An affinity index, which we defined median binding concentration BC50 in analogy to the IC50 parameter, intended to address the general issue of comparing dimensionally heterogeneous binding data, and a limiting BC500 quantity describing intrinsic binding affinities were developed for evaluating the results. BC500 values for la range from 1 to 6 mM, indicating an intrinsic binding affinity in the millimolar range and a selectivity factor of 5 toward the investigated glycosides. The treatment has been extended to include any generic host-guest system involved in single or multiple binding equilibria.
• Synthesis of a new tripodal chemosensor based on 2,4,6-triethyl-1,3,5-trimethylbencene scaffolding bearing thiourea and fluorescein for the chromo-fluorogenic detection of anions
  作者：María E. Moragues、Luis E. Santos-Figueroa、Tatiana Ábalos、Félix Sancenón、Ramón Martínez-Máñez

  DOI：10.1016/j.tetlet.2012.07.039

  日期：2012.9

  A tripodal receptor containing thiourea as binding site and fluorescein as signalling subunit has been designed, synthesized and used for the colorimetric detection of basic anions in DMSO solutions. (C) 2012 Elsevier Ltd. All rights reserved.