3a,6a-Bis-(4-heptyl-phenyl)-tetrahydro-imidazo[4,5-d]imidazole-2,5-dione | 205862-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3a,6a-Bis-(4-heptyl-phenyl)-tetrahydro-imidazo[4,5-d]imidazole-2,5-dione
• CAS: 205862-09-5
• 化学式: C₃₀H₄₂N₄O₂
• 分子量: 490.689
• InChiKey: MHDRUCGAVMBCKE-RNPORBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  36.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82.26
• 氢给体数：
  4.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3a,6a-Bis-(4-heptyl-phenyl)-tetrahydro-imidazo[4,5-d]imidazole-2,5-dione 在 盐酸 、 氢氧化钾 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Diels−Alder Reactions through Reversible Encapsulation

  摘要：

  Experimental details are given for the preparation of large self-complementary molecules capable of assembly into pseudospherical capsules. These structures exist as hydrogen bended diners in organic solvents, and they form and dissipate on a time scale that permits direct NMR observation of the reversible encapsulation of smaller molecules. The cavity is roomy enough to accommodate more than one molecule, and two solvent molecules such as benzene appear to occupy the resting state of the capsules. Liberation of these solvent molecules is responsible for the unexpected thermodynamic parameters of the encapsulation process. A bimolecular reaction-the Diels-Alder reaction-is shown to be accelerated by the capsule as both reactants can occupy the capsule concurrently. Size selectivity, saturation kinetics, and product inhibition studies point to a reaction that takes place within the capsule.

  DOI：

  10.1021/ja973898+
• 作为产物：
  描述：

  对正庚基苯甲酸 在 lithium-sodium alloy 、 三氟乙酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 20.0h， 生成 3a,6a-Bis-(4-heptyl-phenyl)-tetrahydro-imidazo[4,5-d]imidazole-2,5-dione
  参考文献：
  名称：

  Diels−Alder Reactions through Reversible Encapsulation

  摘要：

  Experimental details are given for the preparation of large self-complementary molecules capable of assembly into pseudospherical capsules. These structures exist as hydrogen bended diners in organic solvents, and they form and dissipate on a time scale that permits direct NMR observation of the reversible encapsulation of smaller molecules. The cavity is roomy enough to accommodate more than one molecule, and two solvent molecules such as benzene appear to occupy the resting state of the capsules. Liberation of these solvent molecules is responsible for the unexpected thermodynamic parameters of the encapsulation process. A bimolecular reaction-the Diels-Alder reaction-is shown to be accelerated by the capsule as both reactants can occupy the capsule concurrently. Size selectivity, saturation kinetics, and product inhibition studies point to a reaction that takes place within the capsule.

  DOI：

  10.1021/ja973898+

文献信息

• Chiral Softballs:  Synthesis and Molecular Recognition Properties
  作者：José M. Rivera、Tomás Martín、Julius Rebek

  DOI：10.1021/ja004080i

  日期：2001.6.1

  dimeric softball chiral although the monomer itself is achiral. The dimers represent capsules with dissymmetric cavities with volumes ranging from 190 to 390 A(3). The cavities are distorted spheres, and asymmetric guests, such as naturally occurring terpenes, generally prefer one enantiomer of the capsule to its mirror image. The selectivities are moderate (up to 4:1). The complexation studies show that

  对垒球的不同同源物进行了研究，以探索对映选择性封装的结构变体。尽管单体本身是非手性的，但单体亚基中的两个不同的间隔元件使二聚垒球具有手性。二聚体代表具有不对称腔的胶囊，体积范围为 190 到 390 A(3)。空腔是扭曲的球体，不对称的客体，如天然存在的萜烯，通常更喜欢胶囊的一种对映异构体而不是它的镜像。选择性适中（高达 4:1）。络合研究表明，宿主胶囊足够灵活，可以在客体周围舒适地安排自己，但仍保持足够的刚度，以受到手性客体占用的影响。
• Emergent Conformational Preferences of a Self-Assembling Small Molecule:  Structure and Dynamics in a Tetrameric Capsule
  作者：Fraser Hof、Colin Nuckolls、Stephen L. Craig、Tomás Martín、Julius Rebek

  DOI：10.1021/ja002340q

  日期：2000.11.1

  Pendant methoxyl groups are essential for the assembly process and convey their influence through both electronic pathways and surface interactions. Spin polarization transfer experiments show that the capsule undergoes rapid guest-exchange processes while being itself kinetically stable at elevated temperatures.

  在此，我们报告了一种分子的合成，该分子通过氢键自组织成离散的四聚体囊状物质，包裹着大的多环客体分子。组装状态的独特折叠结构由相关光谱结合分子建模确定。悬垂的甲氧基对于组装过程至关重要，并通过电子途径和表面相互作用传达它们的影响。自旋极化转移实验表明，胶囊经历快速的客体交换过程，同时本身在高温下动力学稳定。