3-(芘-1-基)丙基异氰酸酯 | 496811-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 3-(芘-1-基)丙基异氰酸酯
• 英文名称: 3-(pyren-1-yl)propylisocyanate
• 英文别名: 3-pyrenyl-1-isocyanatopropane；3-pyrenylpropylisocyanate；1-(3-Isocyanatopropyl)pyrene
• CAS: 496811-32-6
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: CNRWQWMRWDRRPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 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：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(芘-1-基)丙基异氰酸酯 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以0.69 g的产率得到3-(pyren-1-yl)propylamine
  参考文献：
  名称：

  硅胶和多孔石墨碳作为HPLC中手性选择剂的载体材料的比较

  摘要：

  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。

  DOI：

  10.1016/s0957-4166(02)00585-2
• 作为产物：
  描述：

  芘 在 四氯化钛 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.83h， 生成 3-(芘-1-基)丙基异氰酸酯
  参考文献：
  名称：

  发色团淬灭标记：一种用于量化催化剂形态的方法，如（EBI）ZrMe 2 / B（C 6 F 5）3催化的1-己烯聚合

  摘要：

  含发色团的淬灭剂2和3能够通过折射率（RI）和紫外检测的凝胶渗透色谱（GPC）定量定量活性部位计数并确定活性催化剂聚合基团的质量分布，从而通过（EBI）催化1-己烯的聚合反应ZrMe 2 / B（C 6 F 5）3。通过动力学模型分析了催化剂形态数据的时间演变以及单体消耗，端基生成和本体分子量分布数据的时间分布，以确定通过将己烯插入Zr-Me键引发的速率常数（k i），传播（k p），链转移形成亚乙烯基（k 1,2）和亚乙烯基（k 2,1）端基，并从Zr–H键（k r）重新引发。与以前的模型假定快速重新启动催化剂不同，该分析表明k r比k p慢得多。催化剂形态数据对于进行这种区分至关重要。这项研究表明，使用2和3对生色团进行淬灭标记可以使用带有UV和RI检测器的GPC快速，定量地分析催化烯烃聚合反应的详细动力学模型。

  DOI：

  10.1021/acscatal.6b01819

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。
• Internal Probing of the Supramolecular Organization of Pyrene-Based Organogelators
  作者：Thanh-Loan Lai、David Canevet、Narcis Avarvari、Marc Sallé

  DOI：10.1002/asia.201500395

  日期：2016.1

  A thorough study of the unexpected spectroscopic behavior of two new luminescent pyrene‐urea‐based organogelators is rationalized as a function of their aggregation state and provides a key method to probe the supramolecular organization of the material.

  通过对两种新型pyr基-脲基有机胶凝剂的意外光谱行为的深入研究，可以根据其聚集态进行合理化研究，并为探查该材料的超分子组织提供了一种关键方法。
• Morphological control and molecular recognition by bis-urea hydrogen bonding in micelles of amphiphilic tri-block copolymers
  作者：Natalia Chebotareva、Paul H. H. Bomans、Peter M. Frederik、Nico A. J. M. Sommerdijk、Rint P. Sijbesma

  DOI：10.1039/b507171b

  日期：——

  Hydrogen bonding between urea groups of amphiphilic tri-block copolymers considerably affects their self-assembly in water, which results in a strong modification of morphology and viscosity of aqueous solutions; the hydrogen bonding motif in these amphiphilic copolymers allows molecular recognition of small molecules with complementary hydrogen bonding units.

  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。
• Excimer Emission Properties on Pyrene-Labeled Protein Surface: Correlation between Emission Spectra, Ring Stacking Modes, and Flexibilities of Pyrene Probes
  作者：Akira Fujii、Yutaka Sekiguchi、Hiroyoshi Matsumura、Tsuyoshi Inoue、Wen-Sheng Chung、Shun Hirota、Takashi Matsuo

  DOI：10.1021/acs.bioconjchem.5b00026

  日期：2015.3.18

  The excimer emission of pyrene is popularly employed for investigating the association between pyrene-labeled biomolecules or between pyrene-labeled places in a biomolecule. The property of pyrene excimer emission is affected by the fluctuation in ring stacking modes, which originates from the structural flexibilities of pyrene probes and/or of labeled places. Investigations of the excimer emission

  popular的准分子发射被广泛用于研究label标记的生物分子之间或pyr分子中places标记的位置之间的缔合。ring受激准分子发射的特性受环堆积模式波动的影响，该波动起因于of探针和/或标记位置的结构柔韧性。根据of堆积模式的动力学研究准分子发射提供了provide标记位置之间的详细空间信息。为了评估探针结构和fluctuation-py缔合模式的波动对其在蛋白质表面上发射性质的影响，合成了三种类型的具有不同接头长度的and探针，并将其与A55C / C77S / V169C突变体中的两个半胱氨酸残基偶联腺苷酸激酶（Adk）一种在OPEN和CLOSED形式之间显示结构转换的酶。在具有短接头的pyr探针标记的Adk的封闭形式中，发现受激准分子的发射主要是由pyr的基态缔合引起的。通过X射线晶体学分析成功地确定了蛋白质表面上的pyr堆积结构。但是，蛋白质中的发射衰减表明溶液中存在多个堆
• Complexation of Anions Including Nucleotide Anions by Open-Chain Host Compounds with Amide, Urea, and Aryl Functions
  作者：Frank Werner、Hans-Jörg Schneider

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

  日期：2000.2.16

  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.