4-(pyren-1-yl)butyrylazide | 496811-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 4-(pyren-1-yl)butyrylazide
• 英文别名: 4-pyren-1-ylbutanoyl azide
• CAS: 496811-31-5
• 化学式: C₂₀H₁₅N₃O
• 分子量: 313.359
• InChiKey: JZRDKHDWKHGZNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(pyren-1-yl)butyrylazide 以 乙腈 为溶剂， 反应 5.0h， 生成 3-(芘-1-基)丙基异氰酸酯
  参考文献：
  名称：

  Morphological control and molecular recognition by bis-urea hydrogen bonding in micelles of amphiphilic tri-block copolymers

  摘要：

  两亲性三嵌段共聚物的脲基之间的氢键作用对其在水中的自组装有很大影响，从而对水溶液的形态和粘度产生强烈的改变；这些两亲性共聚物中的氢键图案允许分子识别具有互补氢键单元的小分子。

  DOI：

  10.1039/b507171b
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 0.25h， 生成 4-(pyren-1-yl)butyrylazide
  参考文献：
  名称：

  Complexation of Anions Including Nucleotide Anions by Open-Chain Host Compounds with Amide, Urea, and Aryl Functions

  摘要：

  A systematical evaluation of association constants between halide, phosphate, and carboxylate anions with N-methylformamide (1) and the related bidentate receptors 2-6 (derived from, e.g., phthalic acid or ethylenediamine) in CDCl3 as solvent yielded increments of complexation free-energy Delta Delta G for each single H-bond, which varied like, e.g., 5.1 kJ/mol (for Cl-), 4.0 kJ/mol (for Br-), 4.0 kJ/mol (for I-) (with values taken from Tables 1 and 2), in line with expected H-bond strength. The observed complexation induced NH-NMR shift (CIS) values also showed a regular change, in the case of 1 e.g., from 5.0 to 2.8 to 2.1 ppm (Table 1), with about half of these values with the bidentate ligands (Tables 2 and 3). Tridentate hosts led to a substantial binding increase, if strain-free convergence of all NH donor functions towards the anion was possible. The tris[urea] ligand 10 yielded, even in the polar solvent DMSO, with Cl- a Delta G of - 21.5 kJ/mol and with Br- of - 10.5 kJ/mol, whereas with I-, no association was detectable. The results demonstrated that small, inexpensive, and conformationally mobile host compounds can exhibit high affinities as well as descrimination with anions, as much as more preorganized receptors do which require multistep synthesis. The corresponding adamantyl derivative 13 allowed measurements also in CDCl3, with K = 4.3 . 10(4) M-1 for chloride (Table 7). Complexes with nucleotide anions were again particularly strong with the tridentate urea-based ligands, the latter being optimal ligands for chloride complexation. For the association of 10 with AMP(2-) and GMP(2-)in (D-6)DMSO, the association constants were 3 . 10(4) M-1 (Table 8) and almost the: same as with Cl-. In the case of the urea derivatives 17 18, and 21, containing only one phenyl or pyrenyl substituent, however, the Delta G values decreased in the order A > C > T > G (e.g. - 13.6, - 11.6, - 7.6, - 10.5 kJ/mol in the case of 17 resp.; Table 8). In H2O, the pyrenyl-substituted urea derivatives allow measurements with fluorescence, and, unexpectedly show only smaller nucleobase discrimination, with constants around 3 . 10(3) M-1.

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<465::aid-hlca465>3.0.co;2-f

文献信息

• Synthetic studies on 4,5-dihydro-3H-1,2,4-triazole-3,5-diones bearing fluorogenic residues at N-4
  作者：Gordon Read、Nigel R. Richardson

  DOI：10.1039/p19960000167

  日期：——

  A number of fluorescent 4,5-dihydro-3H-1,2,4-triazole-3,5-diones have been made. Intra-inter-electrophilic substitution by the triazoledione moiety on the activated naphthalene ring of 4-[6-(5-dimethylamino-1-naphthylsulfonamido)hexyl]-4,5-dihydro-3H-1,2,4-triazole-3,5-dione 4a3 leads to rapid decomposition. The dienophilicity of the triazoledione moiety in 4-pyren-1-yl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione 4d is dramatically lowered by steric shielding. Insertion of a three-carbon spacer unit into the latter compound, to give the 3-pyren-1-ylpropyl analogue 4e, affords a valuable fluorogenic reagent for the analysis of trace levels of 1,3-dienes. Powdered barium manganate is shown to be an excellent solid-phase oxidant for conversion of urazoles into 1,2,4-triazole-3,5-diones.

  已经合成了一些荧光的4,5-二氢-3H-1,2,4-三唑-3,5-二酮。在4-[6-(5-二甲氨基-1-萘磺酰胺)己基]-4,5-二氢-3H-1,2,4-三唑-3,5-二酮4a3的活化萘环上，三唑二酮基团的内外电亲核取代反应导致快速分解。4-芘-1-基-4,5-二氢-3H-1,2,4-三唑-3,5-二酮4d中的三唑二酮基团的二烯亲和性因空间位阻而显著降低。在后者化合物中插入一个三碳间隔单元，生成3-芘-1-基丙基类似物4e，为分析微量1,3-二烯提供了一种有价值的荧光试剂。粉末状锰酸钡被证明是一种优良的固相氧化剂，可以使尿唑转化为1,2,4-三唑-3,5-二酮。
• A comparison of silica and porous graphitic carbon as support materials for a chiral selector in HPLC
  作者：Joakim Oxelbark、Sofia Claeson

  DOI：10.1016/s0957-4166(02)00585-2

  日期：2002.10

  The tartaramide based chiral selector 2 was synthesized, coated onto porous graphitic carbon (PGC), and evaluated as a chiral stationary phase for HPLC. Its performance was compared to the silica based sorbent 1, containing the same chiral moiety. The retention and separation characteristics of the two columns were found to be correlated, but separation factors and column efficiencies were constantly

  合成了基于酒石酰胺的手性选择剂2，将其涂覆在多孔石墨碳（PGC）上，并评价为HPLC的手性固定相。将其性能与包含相同手性部分的二氧化硅基吸附剂1进行了比较。发现两个色谱柱的保留和分离特性是相关的，但是PGC色谱柱的分离因子和色谱柱效率始终较低。评价了PGC的涂层作为评价手性选择剂的新颖和简单的方法。