ethyl trans-3-(1-pyrenyl)propenoate | 103682-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: ethyl trans-3-(1-pyrenyl)propenoate
• 英文别名: (E)-ethyl 3-(pyren-1-yl)acrylate；(E)-ethyl-3-(pyren-1-yl)acrylate；Ethyl 3-(1'-pyrenyl)-acrylate；Ethyl trans-3-(1-pyrenyl)-2-propenoate；ethyl (E)-3-pyren-1-ylprop-2-enoate
• CAS: 103682-14-0
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: QUTBFWCVWNSATR-ACCUITESSA-N

物化性质

• 沸点：
  492.7±14.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  ethyl trans-3-(1-pyrenyl)propenoate 在 palladium on activated charcoal sodium tetrahydroborate 、 氢氟酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 生成 Pentacyclo[9.6.2.02,6.08,18.015,19]nonadeca-1(18),2(6),7,11(19),12,14-hexaen-5-ol
  参考文献：
  名称：

  Synthesis of 7H- and 9H-cyclopenta[a]pyrene

  摘要：

  DOI：

  10.1021/jo00143a047
• 作为产物：
  描述：

  1-芘甲醛 在 碘 、 对甲苯磺酸 、 锌 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 ethyl trans-3-(1-pyrenyl)propenoate
  参考文献：
  名称：

  Synthesis of 7H- and 9H-cyclopenta[a]pyrene

  摘要：

  DOI：

  10.1021/jo00143a047

文献信息

• A simple visual sensor with the potential for determining the concentration of fluoride in water at environmentally significant levels
  作者：Tomoki Nishimura、Su-Ying Xu、Yun-Bao Jiang、John S. Fossey、Kazuo Sakurai、Steven D. Bull、Tony D. James

  DOI：10.1039/c2cc36107h

  日期：——

  We have developed a simple and robust fluorescence based boronic-acid molecular sensor for determining the concentration of fluoride in water at environmentally significant levels. The simplicity of the method and the ability to measure fluoride in water between 0.1 and 1.5 ppm is particularly noteworthy given the WHO requirements for detecting levels of fluoride in drinking water below 1.5 ppm.

  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。
• 3-Pyrenylacrylates: Synthetic, Photophysical, Theoretical and Electrochemical Investigations
  作者：Sebastian Reimann、Muhammad Sharif、Kai Wittler、Leif R. Knöpke、Annette-E. Surkus、Christian Roth、Ralf Ludwig、Peter Langer

  DOI：10.5560/znb.2013-3004

  日期：2013.4.1

  the absorbance spectra obtained from photophysical measurements are compared with the results of theoretical calculations performed by time dependent TD-B3LYP methods using the 6-31G* basis set. Graphical Abstract 3-Pyrenylacrylates: Synthetic, Photophysical, Theoretical and Electrochemical Investigations

  1-溴芘与丙烯酸酯的 Mizoroki-Heck 偶联以非常好的产率（高达 93%）方便地获得各种 3-芘丙烯酸酯。研究了它们的光物理特性和溶剂致变色效应。此外，电化学氧化电位通过 DPV（差分脉冲伏安法）测量确定。将从光物理测量获得的吸收光谱的精细结构与使用 6-31G* 基组的时间相关 TD-B3LYP 方法进行的理论计算结果进行比较。图形摘要 3-芘丙烯酸酯：合成、光物理、理论和电化学研究
• Barium Hydroxide as Catalyst in Organic Reactions; V. Application in the Horner Reaction under Solid-Liquid Phase-Transfer Conditions
  作者：J. V. Sinisterra、Z. Mouloungui、M. Delmas、A. Gaset

  DOI：10.1055/s-1985-31438

  日期：——

  A new application of a barium hydroxide catalyst for the Horner reaction is described. The scope of the synthetic method is shown; furthermore, the yields are higher and the reaction times shorter than those previously reported for similar experimental conditions (solid-liquid). Ethyl 3-(1′-pyrenyl)-acrylate and the 3-(1′-pyrenyl)-acrylonitrile are described for the first time.

  介绍了氢氧化钡催化剂在霍纳反应中的新应用。此外，与之前报道的类似实验条件（固-液）相比，该合成方法的产率更高、反应时间更短。首次描述了 3-(1′-芘基)-丙烯酸乙酯和 3-(1′-芘基)-丙烯腈。
• Aerobic Palladium(II)-Catalyzed Dehydrogenative Heck Reaction in the Synthesis of Pyrenyl Fluorophores. A Photophysical Study of β-Pyrenyl Acrylates in Solution and in the Solid State
  作者：Michał Piotrowicz、Janusz Zakrzewski、Rémi Métivier、Arnaud Brosseau、Anna Makal、Krzysztof Woźniak

  DOI：10.1021/jo502619k

  日期：2015.3.6

  An aerobic dehydrogenative Heck reaction of pyrene (1a) and 2,7-di-tert-butylpyrene (1b) with ethyl acrylate is reported. The reaction is catalyzed by a Pd(OAc)2/4,5-diazafluoren-9-one (DAF) system and takes place in acetic or pivalic acid as solvents at 110-130 degrees C. The reaction of 1a afforded a 6:1 mixture of C-1- and C-4-alkenylated pyrenes (2a and 3a, respectively) in 71% yield. In the case of 1b, only a C-4-substituted product (3b) was formed in 46% yield. Compounds 2a and 3a,b exhibited fluorescence in solution and in the solid state. In chloroform and THF solution the fluorescence maxima were in the range of 440-465 nm, and quantum yields decreased in the order 2a > 3a> 3b. In the solid state, 3a,b showed blue-green fluorescence (Phi(F) = 0.26 and 0.14, respectively), whereas 2a emitted yellow-green fluorescence) (Phi(F) = 0.35). Besides blue-emitting monomers, the presence of green-emitting aggregated species (preformed dimers) in the crystals of 3a,b and red-emitting dynamic excimers in the crystals of 2a has been demonstrated. Single-crystal X-ray diffraction analyses of 2a and 3b confirmed pi-stacking of pyrenyl moieties in the crystals of the former and the absence of stacking in the crystals of the latter compound.
• LEE, H.;HARVEY, R. G., J. ORG. CHEM., 1982, 47, N 22, 4364-4367
  作者：LEE, H.、HARVEY, R. G.

  DOI：——

  日期：——