| 258277-29-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 258277-29-1
• 化学式: C₁₄H₁₈N₄O₈
• 分子量: 370.319
• InChiKey: DMRCYBNPXYCYLS-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.13
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  118.16
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 168000.0h， 以80%的产率得到
  参考文献：
  名称：

  用于合成葫芦[ n ]尿素的甘脲单体的制备

  摘要：

  带有游离脲基（1）和双（环醚）（2）的甘脲衍生物是合成葫芦素，其衍生物及其同类物的基本组成部分。已知的1和2衍生物分为两大类-凸面上带有烷基或芳基官能团的衍生物。在本文中，我们提出了第三类甘脲，即那些带有取代基的吸电子特征的甘脲。这类化合物在其凸面上带有羧酸衍生的官能团，并且衍生自二酯1e和2e。1e和2e的改进合成报告并描述其修改。例如，1E和2E被转换成仲酰胺（10 - 15通过在纯的伯胺的溶液加热）。的仲酰胺可转化为酰亚胺（19 - 22，24，25）通过在与CLCH PTSA加热2 CH 2 CL上。通过简单，可扩展的洗涤或重结晶程序即可以高收率分离出纯净形式的这些化合物。我们还介绍了双（环醚）2e，8和22的X射线晶体学表征。我们预计1和2的酯，羧酸酯，酸，仲酰胺，酰亚胺和叔酰胺衍生物的现成可用性将通过提供一类具有吸电子取代基的新型结构单元来扩展葫芦素衍生物的合成范围。

  DOI：

  10.1016/s0040-4020(03)00150-9
• 作为产物：
  描述：

  聚合甲醛 、 1,5-bis(carboxyethyl)glycoluril 在 三氟乙酸 作用下， 以45%的产率得到
  参考文献：
  名称：

  Design, synthesis and self-association behavior of water soluble self complementary facial amphiphiles

  摘要：

  甘氨酰的自互补表面两亲性衍生物是在水中进行疏水自组装的有用构件；我们介绍了六种二聚体自组装结构的设计、合成和表征，这些结构在 pD 7.4 缓冲 D2O 中的 KS 值高达 1840 M-1。

  DOI：

  10.1039/a907474k
• 作为试剂：
  描述：

  在 硫酸 、 potassium iodide 、 4,8-dioxo-2,6-dioxa-3a,4a,7a,8a-tetraaza-cyclopenta[def]fluorene-8b,8c-dicarboxylic acid diethyl ester 作用下， 以 水 为溶剂， 反应 0.5h， 以96%的产率得到Cucurbituril
  参考文献：
  名称：

  Synthesis and Self-Assembly Processes of Monofunctionalized Cucurbit[7]uril

  摘要：

  We present a building-block approach toward functionalized CB[7] derivatives by the condensation of methylene-bridged glycoluril hexamer 1 and glycoluril bis(cyclic ethers) 2 and 12. The CB[7] derivatives Me2CB[7] and CyCB[7] are highly soluble in water (264 mM and 181 mM, respectively). As a result of the high intrinsic solubility of Me2CB[7], it is able to solubilize the insoluble benzimidazole drug albendazole. The reaction of hexamer 1 with glycoluril derivative 12, which bears a primary alkyl chloride group, gives CB[7] derivative 18 in 16% isolated yield. Compound 18 reacts with NaN3 to yield azide-substituted CB[7] 19 in 81% yield, which subsequently undergoes click reaction with propargylammonium chloride (21) to yield CB[7] derivative 20 in 95% yield, which bears a covalently attached triazolyl ammonium group along its equator. The results of NMR spectroscopy (H-1, variable-temperature, and DOSY) and electrospray mass spectrometry establish that 20 undergoes self-assembly to form a cyclic tetrameric assembly (20(4)) in aqueous solution. CB[7] derivatives bearing reactive functional groups (e.g., N-3, Cl) are now available for incorporation into more complex functional systems.

  DOI：

  10.1021/ja3058502

文献信息

• An original self-assembly using a tetrathiafulvalene-based molecular clip for the recognition of fullerene C₆₀
  作者：Yoann Cotelle、Marie Hardouin-Lerouge、Elise Lemasson、Yohann Morille、David Canevet、Stéphanie Legoupy、Piétrick Hudhomme

  DOI：10.1039/c9cc09633g

  日期：——

  A glycoluril-based molecular clip incorporating two tetrathiafulvalene (TTF) sidewalls has been synthesized using a straightforward Diels-Alder synthetic route and its ability to self-assemble with fullerene C60 in a 2 : 1 stoichiometry has been demonstrated in solution.

  已经使用简单的Diels-Alder合成路线合成了包含两个四硫富瓦烯（TTF）侧壁的基于甘脲的分子夹，并且已在溶液中证明了其以2：1的化学计量与富勒烯C60自组装的能力。
• Cucurbit[<i>n</i>]uril Analogues
  作者：Jason Lagona、James C. Fettinger、Lyle Isaacs

  DOI：10.1021/ol035468w

  日期：2003.10.1

  Cucurbits come in a variety of sizes, shapes, and colors. We present a building block approach that allows the tailor-made synthesis of CB[5], CB[6], and CB[7] analogues whose sizes, shapes, and colors differ from those of the known CB[n].
• Cucurbit[<i>n</i>]uril Analogues:  Synthetic and Mechanistic Studies
  作者：Jason Lagona、James C. Fettinger、Lyle Isaacs

  DOI：10.1021/jo051655r

  日期：2005.12.1

  The synthesis of cucurbit[n]uril analogues (18, 19, (+/-)-20, 33, 34, 35, 36, and 37) is presented. These CB[5], CB[6], and CB[7] analogues all contain bis(phthalhydrazide) walls that are incorporated into the macrocycle. The tailor-made synthesis of these CB[n] analogues proceeds by the condensation of the appropriate bis(electrophile) (4, 7, or 9) with bis(phthalhydrazide) (17), which delivers the CB[6] and CB[7] analogues in good yield, whereas the CB[5] analogue is formed in low yield. To improve the solubility characteristics of the CB[n] analogues for recognition studies in water or organic solution, the CO2Et groups were transformed to CO2H and CO2(CH2)(9)CH3 groups. On the basis of the results of product resubmission experiments, we conclude that these macrocycles are kinetic products. To help rationalize the good yields obtained in the CB [6] and CB [7] analogue macrocyclization reactions, we performed mechanistic studies of model methylene bridged glycoluril dimers, which suggest an intramolecular isomerization during CB[n] analogue formation.
• Self-Sorting Molecular Clips
  作者：Soumyadip Ghosh、Anxin Wu、James C. Fettinger、Peter Y. Zavalij、Lyle Isaacs

  DOI：10.1021/jo8009424

  日期：2008.8.1

  We report the synthesis and characterization of 12 C-shaped methylene-bridged glycoluril dimers (1-12) bearing H-bonding groups on their aromatic rings. Compounds 1, 2, (+/-)-4a, (+/-)-5, (+/-)-7, and 8 form tightly associated homodimers in CDCl3, due to the combined driving force of pi-pi and H-bonding interactions. Compounds 2, ()-5, and 8, having disparate spatial distribution of their H-bonding groups, display the ability to efficiently distinguish between self and nonself even within three-component mixtures in CDCl3. When the spatial distributions of the H-bonding groups of the molecular clips are similar (e.g., 1 and 2), a mixture of homodimers and heterodimers is formed. The effect of various structural modifications (e.g., chirality, side chain steric bulk, number and pattern of H-bonds) on the strength of self-assembly and the fidelity of self-sorting are presented. On the basis of these results we prepared self-sorting systems comprising three (e.g., 1, (+/-)-5, and (+/-)-7) and even four (2, (+/-)-5, 9, and 10) components. The potential of molecular clips 1-12 as robust, functionalizable, self-sorting modules to control the noncovalent interaction network in systems chemistry studies is described.
• Synthesis, structural characterization, and fluorescent chemosensory properties of novel molecular clips based on diethoxycarbonyl glycoluril
  作者：Sheng-Li Hu、Neng-Fang She、Guo-Dong Yin、Hui-Zhen Guo、An-Xin Wu、Chu-Luo Yang

  DOI：10.1016/j.tetlet.2006.12.138

  日期：2007.2

  A pair of novel fluorescent molecular clips was synthesized from diethoxycarbonal glycoluril cyclic ether and 1,2-dihydroindazol-3-one. Their structures and conformations were confirmed by single crystal X-ray diffraction and chemosensory properties were studied by fluorescent spectroscope. Both of them exhibited selective recognition toward Fe3+ over other metal ions examined in DMF/CH3OH (50:1, v/v). (c) 2007 Elsevier Ltd. All rights reserved.