diethyl 5-ethynylisophthalate | 368455-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 5-ethynylisophthalate
• 英文别名: diethyl 5-ethynylbenzene-1,3-dicarboxylate
• CAS: 368455-18-9
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: JVGOYLBCMZYXCT-UHFFFAOYSA-N

物化性质

• 沸点：
  365.9±32.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 5-ethynylisophthalate 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 乙醇 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 diethyl 5-[(4-[(4-ethynylphenyl)ethynyl]phenyl)ethynyl]isophthaloate
  参考文献：
  名称：

  Tetrahedral Onsager Crosses for Solubility Improvement and Crystallization Bypass

  摘要：

  Pure organic molecules exhibiting a suitable concave rigid shape are expected to give porous glasses in the solid state. Such a feature opens new opportunities to avoid crystallization and to improve molecular solubility in relation to the high internal energy of these solid phases. To quantitatively explore the latter strategy, a series of rigid tetrahedral conjugated molecules nC and the corresponding models nR have been synthesized. Related to the present purpose, several properties have been investigated using UV absorption, steady-state fluorescence emission, differential scanning calorimetry, H-1 NMR translational self-diffusion, magic angle spinning C-13 NMR, and multiple-beam interferometry experiments. The present tetrahedral crosses are up to 8 orders of magnitude more soluble than the corresponding model compounds after normalization to the same molecular length. In addition, they give concentrated monomeric solutions that can be used to cover surfaces with homogeneous films whose thickness goes down to the nanometer range. Such attractive features make cross-like molecular architectures promising for many applications.

  DOI：

  10.1021/ja010019h
• 作为产物：
  描述：

  diethyl 5-iodoisophthalate 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 乙醇 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 diethyl 5-ethynylisophthalate
  参考文献：
  名称：

  Tetrahedral Onsager Crosses for Solubility Improvement and Crystallization Bypass

  摘要：

  Pure organic molecules exhibiting a suitable concave rigid shape are expected to give porous glasses in the solid state. Such a feature opens new opportunities to avoid crystallization and to improve molecular solubility in relation to the high internal energy of these solid phases. To quantitatively explore the latter strategy, a series of rigid tetrahedral conjugated molecules nC and the corresponding models nR have been synthesized. Related to the present purpose, several properties have been investigated using UV absorption, steady-state fluorescence emission, differential scanning calorimetry, H-1 NMR translational self-diffusion, magic angle spinning C-13 NMR, and multiple-beam interferometry experiments. The present tetrahedral crosses are up to 8 orders of magnitude more soluble than the corresponding model compounds after normalization to the same molecular length. In addition, they give concentrated monomeric solutions that can be used to cover surfaces with homogeneous films whose thickness goes down to the nanometer range. Such attractive features make cross-like molecular architectures promising for many applications.

  DOI：

  10.1021/ja010019h

文献信息

• 1,3,5-Triphenylbenzene fluorophore as a selective Cu²⁺sensor in aqueous media
  作者：Sakan Sirilaksanapong、Mongkol Sukwattanasinitt、Paitoon Rashatasakhon

  DOI：10.1039/c1cc16148b

  日期：——

  Three water-soluble fluorophores are synthesized from 1,3,5-tris-(4′-iodophenyl)benzene. The compound with salicylate groups exhibits a selective fluorescent quenching by Cu2+via a static quenching mechanism. The addition of Triton X-100 improves the quantum efficiency of the fluorophore as well as the detection limit for Cu2+ from 6.49 to 0.19 ppb.

  三种水溶性荧光团由1,3,5-三(4'-碘苯基)苯合成。其中带有水杨酸基团的化合物通过静态淬灭机制对Cu²⁺表现出选择性荧光淬灭。加入Triton X-100不仅提高了荧光团的量子效率，还将Cu²⁺的检测限从6.49 ppb降低到了0.19 ppb。
• One-Pot Dual Catalysis of a Photoactive Coordination Polymer and Palladium Acetate for the Highly Efficient Cross-Coupling Reaction via Interfacial Electron Transfer
  作者：Zhifen Guo、Xin Liu、Yan Che、Dashu Chen、Hongzhu Xing

  DOI：10.1021/acs.inorgchem.1c03961

  日期：2022.2.7

  charge generation was synthesized via a solvothermal reaction. The synthesized CP was successfully applied to the photocatalytic C–C cross-coupling reaction via the one-pot dual-catalysis method, in combination with the simple and ligand-free palladium salt of Pd(OAc)2 as a metal catalyst. The reaction features a short reaction time, mild reaction conditions, good recyclability, and a high yield of

  我们在此报告了对直接一锅双催化策略的探索，即光活性配位聚合物（CP）与另一种金属催化剂的直接结合，以进行理想的光诱导有机转化。该策略克服了在我们的案例中已被证明无效的金属/CP复合材料预合成的必要性。通过溶剂热反应合成了一种新的二维 CP，该二维 CP 显示出宽范围可见光吸收和高效光致电荷产生的理想特性。合成的 CP 通过一锅双催化法与简单且无配体的 Pd(OAc) 2钯盐相结合，成功应用于光催化 C-C 交叉偶联反应。作为金属催化剂。该反应具有反应时间短、反应条件温和、可回收性好、从多种底物得到Heck产物的高收率等特点。对比实验表明，预合成的 Pd/CP 复合材料对该反应无效，证明了一锅双催化策略的重要性。机理研究表明，一锅法反应依赖于合成 CP 的光催化产生反应性芳基自由基和 Pd 催化产生目标产物之间的协同作用，其中界面电子转移已被证明对于产生瞬态和催化反应至关重要CP 表面附近的活性
• Supramolecular polymer for explosives sensing: role of H-bonding in enhancement of sensitivity in the solid state
  作者：Bappaditya Gole、Sankarasekaran Shanmugaraju、Arun Kumar Bar、Partha Sarathi Mukherjee

  DOI：10.1039/c1cc13925h

  日期：——

  A π-electron rich supramolecular polymer as an efficient fluorescent sensor for electron deficient nitroaromatic explosives has been synthesized, and the role of H-bonding in dramatic amplification of sensitivity/fluorescence quenching efficiency in the solid state has been established.

  我们合成了一种富含 π 电子的超分子聚合物，它是一种高效的缺电子硝基芳香族炸药荧光传感器，并确定了 H 键在固态灵敏度/荧光淬灭效率急剧放大中的作用。
• High Gas Adsorption Capacity of an <i>agw</i> ‐Type Metal–Organic Framework Decorated with Methyl Groups
  作者：Liting Du、Zhiyong Lu、Li Xu、Mengtao Ma、Jinchi Zhang

  DOI：10.1002/ejic.201600576

  日期：2016.10

  A new methyl-functionalized metal-organic framework, Cu3(CMPEIP)2*2H2O}n (m-NB13, H3CMPEIP = 5-((4-carboxy-2-methylphenyl)ethynyl)isophthalic acid) was solvothermally synthesized and structurally characterized. Cu3(CMPEIP)2*2H2O}n exhibits a high BET surface area of 3215.4 m2 g1, large H2 uptake (1.92 wt% at 1 bar and 77 K), and excellent CO2 storage capacity(9.24 wt% at 1 bar and 298 K).

  一种新的甲基功能化金属有机骨架 Cu3(CMPEIP)2*2H2O}n (m-NB13, H3CMPEIP = 5-((4-carboxy-2-methylphenyl)ethynyl)isophthalic acid) 溶剂热合成和结构表征. Cu3(CMPEIP)2*2H2O}n 具有 3215.4 m2 g1 的高 BET 表面积、大量的 H2 吸收量（1 bar 和 77 K 时为 1.92 wt%）和出色的 CO2 储存能力（1 bar 和 298 K)。
• Anthracene-based indium metal–organic framework as a promising photosensitizer for visible-light-induced atom transfer radical polymerization
  作者：Xingyu Li、Dashu Chen、Yue Liu、Ziyang Yu、Qiansu Xia、Hongzhu Xing、Wendong Sun

  DOI：10.1039/c6ce00465b

  日期：——

  distribution and high retention of chain-end groups have been prepared. The kinetics study reveals that the MOF-mediated ATRP shows characteristics of controlled radical polymerization (CRP). Besides, the polymerization can be easily regulated by light. Furthermore, the heterogeneous MOF can be easily recovered from the reaction and recycled for the photopolymerization. This study has involved photoactive

  金属有机框架（MOF）为设计和合成用于光化学反应的光敏杂化材料提供了一个有吸引力的平台。我们在这里报告了利用新的可见光响应铟MOF诱导甲基丙烯酸酯单体的原子转移自由基聚合（ATRP），其中设计良好的聚合物具有可控制的分子量，窄的分子量分布和较高的链端基团保留率已经准备好了。动力学研究表明，MOF介导的ATRP具有受控自由基聚合（CRP）的特征。此外，聚合可以容易地通过光调节。此外，非均相的MOF可以容易地从反应中回收并再循环用于光聚合。