3-(pyrene-1-yl)propionic acid ethyl ester | 83671-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 3-(pyrene-1-yl)propionic acid ethyl ester
• 英文别名: ethyl 3-(1-pyrenyl)-2-propanoate；ethyl 3-(pyren-1-yl)propanoate；Ethyl 3-pyren-1-ylpropanoate；ethyl 3-pyren-1-ylpropanoate
• CAS: 83671-44-7
• 化学式: C₂₁H₁₈O₂
• 分子量: 302.373
• InChiKey: JSVZZAKTRDXKGU-UHFFFAOYSA-N

物化性质

• 沸点：
  469.0±14.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(pyrene-1-yl)propionic acid ethyl ester 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-(1-pyrenyl)propionic acid
  参考文献：
  名称：

  P标记的蛋白质表面上的准分子发射特性：发射光谱，环堆积模式和Flex探针的柔性之间的相关性

  摘要：

  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

  DOI：

  10.1021/acs.bioconjchem.5b00026
• 作为产物：
  描述：

  1-芘甲醛 在 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 3-(pyrene-1-yl)propionic acid ethyl ester
  参考文献：
  名称：

  A simple visual sensor with the potential for determining the concentration of fluoride in water at environmentally significant levels

  摘要：

  我们开发出了一种简单而坚固的基于荧光的硼酸分子传感器，用于测定水中对环境有重要影响的氟浓度。鉴于世界卫生组织要求检测饮用水中低于百万分之 1.5 的氟含量，该方法的简便性和测量水中 0.1 至 1.5 ppm 氟含量的能力尤其值得注意。

  DOI：

  10.1039/c2cc36107h

文献信息

• Influence of the catalytic conditions on the selectivity of the Pd-catalyzed Heck arylation of acrolein derivatives
  作者：Sébastien Noël、Laurent Djakovitch、Catherine Pinel

  DOI：10.1016/j.tetlet.2006.03.186

  日期：2006.6

  The Heck arylation of acrolein with a variety of condensed aryl and heteroaryl halides is described. Depending on the substrate, up to 87% isolated yield to the expected aldehydes was achieved. When the reaction was run on diethylacetal acrolein, the choice of catalytic system dramatically affected the selectivity of the reaction: the catalyst system based on Herrmann’s palladacycle complex gave mainly

  描述了丙烯醛与各种缩合的芳基和杂芳基卤化物的Heck芳基化反应。取决于底物，获得了高达87％的预期醛分离产率。当反应在二乙缩醛丙烯醛上进行时，催化体系的选择极大地影响了反应的选择性：基于Herrmann的palladacycle配合物的催化剂体系主要产生饱和酯2，而Cacchi的条件导致形成α，β-不饱和醛1。
• Design of Polyaromatic Hydrocarbon-Supported Tin Reagents:  A New Family of Tin Reagents Easily Removable from Reaction Mixtures
  作者：Didier Stien、Stéphane Gastaldi

  DOI：10.1021/jo049868o

  日期：2004.6.1

  We report in this paper the preparation and use of stannanes 11, 12a, and 12b, compounds whose 3-pyrenylpropyl side chain affinity for activated carbon simplifies tin removal and product isolation. Our pyrene-supported reagents can be used for radical reductions and cyclizations (11), radical and cationic allylations (12a), and Stille couplings (12b) in much the same way as tributyltin derivatives

  我们在本文报道的制备和使用锡烷的11，图12A，和12B，化合物，其3- pyrenylpropyl侧链亲和力活性炭简化锡去除和产物分离。我们的pyr支持的试剂可用于自由基还原和环化（11），自由基和阳离子烯丙基化（12a）以及Stille偶联（12b），其方式与三丁基锡衍生物大致相同。
• PAH-supported tin hydride: a new tin reagent easily removable from reaction mixtures
  作者：Stéphane Gastaldi、Didier Stien

  DOI：10.1016/s0040-4039(02)00801-8

  日期：2002.6

  We demonstrate here that a new pyrene-supported tin hydride can be used in radical chemistry. Final products were easily purified by adsorption of the PAH-supported tin side product with activated carbon.

  我们在这里证明了一种新的pyr载氢化锡可用于自由基化学中。通过用活性炭吸附PAH负载的锡副产物，可以轻松纯化最终产物。
• Efficient Heterogeneously Palladium-Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydesor 3-Arylpropionic Esters
  作者：Sébastien Noël、Ciahong Luo、Catherine Pinel、Laurent Djakovitch

  DOI：10.1002/adsc.200600593

  日期：2007.5.7

  A heterogeneous tetrakis(ammine)palladium-NaY zeolite [Pd(NH3)4]/NaY} catalyst was applied successfully to the Heck arylation of acrolein diethyl acetal using a large variety of aryl and heteroaryl bromides. Depending on the reaction conditions (Heck versus Cacchi) good to high selectivities toward the 3-arylpropionic esters or to the cinnamaldehydes were achieved, respectively. Under classical Heck

  使用多种芳基和杂芳基溴化物，成功地将异质四（氨）钯-NaY沸石[Pd（NH 3）4 ] / NaY}催化剂用于丙烯醛二乙缩醛的Heck芳基化反应。取决于反应条件（Heck与分别获得了对3-芳基丙酸酯或对肉桂醛具有良好至高选择性的Cacchi。在经典的Heck条件下，虽然发现催化剂在前两次运行中都稳定，但从第三次循环开始就显示出明显的活性损失。在卡奇条件下，催化剂不能重复使用，因为它会导致高脱卤率。所有结果表明反应通过本体溶液中溶解的钯物质进行（浸出）。如通过透射电子显微镜（TEM）分析所观察到的，虽然这些物种可以在Heck条件下被沸石骨架捕获并稳定，但它们在Cacchi条件下倾向于形成大的钯（0）聚集体，从而导致脱卤而不是预期的颈耦合。
• Global tricompartmental analysis of the fluorescence decay surface of the charged fluorescent probe N,N,N-trimethyl-3-(1-pyrenyl)-1-propanaminium prchlorate
  作者：Bart Hermans、Frans C. De Schryver、Noel Boens、Marcel Ameloot、Robert Jerome、Phillippe Teyssie、Erik Goethals、Etienne Schacht

  DOI：10.1021/j100102a024

  日期：1994.12

  The kinetics of the excited-state processes of the charged fluorescent probe N,N,N-trimethyl-3-(1-pyrenyl)-1-propanaminium perchlorate (PROBE) in tetrahydrofuran are reported. At very low concentrations PROBE decays monoexponentially with a lifetime tau of 236 +/- 1 ns, from which k(01) = 1/tau = 4.2 x 10(6) s(-1) is obtained. Upon addition of the quaternary ammonium salt N,N,N-trimethyl-1-dodecanaminium perchlorate a biexponential decay function is needed to describe the decay traces. The second excited state is the aggregated PROBE. This aggregation is due to dipole-dipole or ion-dipole interactions. The rate constant values of the kinetic Scheme (Scheme 4) are obtained by global bicompartmental analysis: k(01) = k(02), k(21) = (42 +/- 7) x 10(9) M(-1) s(-1); k(12) = (5.7 +/- 0.1) x 10(7) s(-1). When the concentration of PROBE itself is varied, a triple-exponential decay function adequately describes the decay surface. The third excited-stale species is a PROBE excimer, which can be formed through two different pathways: either intermolecularly when a locally excited PROBE molecule encounters a ground-state PROBE molecule or intramolecularly when an aggregate of two PROBE molecules rearranges. To resolve the kinetics of this system, global tricompamnental analysis is developed. Even after including the information available from experiments where N,N,N-trimethyl-1-dodecanaminium perchlorate is added (k(01) = k(02)), and the information available from the global triple-exponential analysis (k(13) = 0 and k(23) = 0) (Scheme 5), the experimental time-resolved data do not allow one to obtain a unique solution for the rate constant values, By scanning the rate constant k31, bounds can be specified for the rate constants: 53 x 10(9) < k(21) < 60 x 10(9) M(-1) s(-1), k(31) < 7 x 10(9) M(-1) s(-1), 1.5 x 10(8) < k(12) < 1.7 x 10(8) s(-1) and k(32) < 2 X 10(7) s(-1). Unique values are obtained for k(01), k(02), and k(O3): k(01) = k(02) = (4.25 +/- 0.01) x 10(7) s(-1); k(03) = (1.92 +/- 0.03) x 10(7) s(-1).