3,3'-(1,4-phenylene)dipropiolic acid | 4843-45-2

• 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: 3,3'-(1,4-phenylene)dipropiolic acid
• 英文别名: 3-[4-(2-carboxyethynyl)phenyl]prop-2-ynoic acid
• CAS: 4843-45-2
• 化学式: C₁₂H₆O₄
• 分子量: 214.177
• InChiKey: IUCPZNVTXMASAX-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C(Solv: methanol (67-56-1))
• 沸点：
  471.9±41.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3'-(1,4-phenylene)dipropiolic acid 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 C₁₆H₃₆N⁽¹⁺⁾*C₃H₃F₂O₂^(1-) 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 1,4-bis((2-methyl-3-((triisopropylsilyl)ethynyl)-2H-isoindol-1-yl)ethynyl)benzene
  参考文献：
  名称：

  Cycloaddition-based Formal C–H Alkynylation of Isoindoles Leading to the Synthesis of Air-stable Fluorescent 1,3-Dialkynylisoindoles

  摘要：

  Reaction of N-alkylisoindoles with (bromoethynyl)triisopropylsilane afforded 1,3-bis(triisopropylsilylethynyl) isoindoles in high yields. The formal C-H alkynylation proceeds under transition-metal-free conditions through [4 + 2] cycloaddition of the pyrrole ring of isoindole with bromoalkyne followed by ring-opening of the product.

  DOI：

  10.1021/ol401051d
• 作为产物：
  描述：

  2,3,2',3'-tetrabromo-3,3'-p-phenylene-di-propionic acid 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3,3'-(1,4-phenylene)dipropiolic acid
  参考文献：
  名称：

  Computational Design of Metal–Organic Frameworks Based on Stable Zirconium Building Units for Storage and Delivery of Methane

  摘要：

  A metal organic framework (MOF) with high volumetric deliverable capacity for methane was synthesized after being identified by computational screening of 204 hypothetical MOF structures featuring (Zr6O4)(OH)(4)(CO2)(n) inorganic building blocks. The predicted MOF (NU-800) has an fcu topology in which zirconium nodes are connected via ditopic 1,4-benzenedipropynoic acid linkers. Based on our computer simulations, alkyne groups adjacent to the inorganic zirconium nodes provide more efficient methane packing around the nodes at high pressures. The high predicted gas uptake properties of this new MOF were confirmed by high-pressure isotherm measurements over a large temperature and pressure range. The measured methane deliverable capacity of NU-800 between 65 and 5.8 bar is 167 cc(STP)/cc (0.215 g/g), the highest among zirconium-based MOFs. High-pressure uptake values of H-2 and CO2 are also among the highest reported. These high gas uptake characteristics, along with the expected highly stable structure of NU-800, make it a promising material for gas storage applications.

  DOI：

  10.1021/cm502304e
• 作为试剂：
  描述：

  甲酸 、 zirconyl chloride octahydrate 在 3,3'-(1,4-phenylene)dipropiolic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Computational Design of Metal–Organic Frameworks Based on Stable Zirconium Building Units for Storage and Delivery of Methane

  摘要：

  A metal organic framework (MOF) with high volumetric deliverable capacity for methane was synthesized after being identified by computational screening of 204 hypothetical MOF structures featuring (Zr6O4)(OH)(4)(CO2)(n) inorganic building blocks. The predicted MOF (NU-800) has an fcu topology in which zirconium nodes are connected via ditopic 1,4-benzenedipropynoic acid linkers. Based on our computer simulations, alkyne groups adjacent to the inorganic zirconium nodes provide more efficient methane packing around the nodes at high pressures. The high predicted gas uptake properties of this new MOF were confirmed by high-pressure isotherm measurements over a large temperature and pressure range. The measured methane deliverable capacity of NU-800 between 65 and 5.8 bar is 167 cc(STP)/cc (0.215 g/g), the highest among zirconium-based MOFs. High-pressure uptake values of H-2 and CO2 are also among the highest reported. These high gas uptake characteristics, along with the expected highly stable structure of NU-800, make it a promising material for gas storage applications.

  DOI：

  10.1021/cm502304e

文献信息

• Catalytic Decarboxylation of Silyl Alkynoates to Alkynylsilanes
  作者：Takahiro Kawatsu、Keiya Aoyagi、Yumiko Nakajima、Jun-Chul Choi、Kazuhiko Sato、Kazuhiro Matsumoto

  DOI：10.1021/acs.organomet.0c00433

  日期：2020.8.24

  silyl alkynoate in N,N-dimethylformamide (DMF) at 80 °C in the presence of catalytic amounts of CuCl and PCy3 produced the corresponding alkynylsilane in excellent yield. The copper-catalyzed decarboxylation proceeded smoothly with low catalyst loadings (0.5 mol % of CuCl and 1.0 mol % of PCy3) under mild reaction conditions and is easily scalable to gram quantities.

  在这里，我们描述了一种用于制备炔基硅烷的脱羧方法。在催化量的CuCl和PCy 3的存在下，于80°C在N，N-二甲基甲酰胺（DMF）中处理炔基硅烷基酯，可以以优异的产率得到相应的炔基硅烷。铜催化的脱羧反应在温和的反应条件下以较低的催化剂负载量（0.5 mol％的CuCl和1.0 mol％的PCy 3）平稳进行，并且易于扩展至克量。
• Silver Nanoparticles Architectured HMP as a Recyclable Catalyst for Tetramic Acid and Propiolic Acid Synthesis through CO ₂ Capture at Atmospheric Pressure
  作者：Swarbhanu Ghosh、Aniruddha Ghosh、Sk Riyajuddin、Somnath Sarkar、Arpita Hazra Chowdhury、Kaushik Ghosh、Sk. Manirul Islam

  DOI：10.1002/cctc.201901461

  日期：2020.2.20

  of the silver nanoparticles (Ag NPs) onto the material. The silver nanoparticle was decorated over the HMP‐2 to prepare the corresponding catalyst (Ag‐HMP‐2). The characterization of the newly produced material has been conducted by N2 adsorption/desorption studies, XPS, FE‐SEM, transmission electron microscopy (TEM) and Powder X‐ray diffraction (PXRD) methods. This microporous catalyst has spectacular

  超交联微孔聚合物（HMP-2）量身定制合成的最新进展凭借其可调节的孔隙率，可操作的设计和绝对有序的结构而聚集了相当多的浓度。这种结构完美的Ag NPs负载的碳催化剂（Ag-HMP-2）是通过无水氯化铁（III）催化的4,4'-双（溴甲基）-1,1'-联苯和咔唑之间的Friedel-Crafts烷基化反应合成的通过将银纳米颗粒（Ag NPs）附着到材料上。将银纳米颗粒装饰在HMP-2上以制备相应的催化剂（Ag-HMP-2）。新生产的材料的表征已由N 2进行吸附/解吸研究，XPS，FE-SEM，透射电子显微镜（TEM）和粉末X射线衍射（PXRD）方法。该微孔催化剂在大气二氧化碳压力下于60°C下具有各种活性，可用于从各种类型的炔丙基胺衍生物生产四酸。在末端炔烃上进行平行固定CO 2的尝试，以在1个大气压下合成丙酸。催化剂（Ag-HMP-2）表现出足够的循环能力，可在不降低催化活性的情况下最多进行五次催化运行，生成四酸和丙酸。
• Flower-like AgNPs@m-MgO as an excellent catalyst for CO₂ fixation and acylation reactions under ambient conditions
  作者：Arpita Hazra Chowdhury、Swarbhanu Ghosh、Sk. Manirul Islam

  DOI：10.1039/c8nj02286k

  日期：——

  Synthesis of fine chemicals from the chemical fixation of CO2 is one of the attractive research areas of today to utilise greenhouse gas CO2 in a greener pathway. A flower-like silver nanoparticle grafted mesoporous magnesium oxide (AgNPs@m-MgO) nanocomposite has been prepared by a facile in situ pathway. The materials are characterised by XRD, FTIR, UV-vis, TG-DTA, FESEM, HR-TEM and N2 adsorption–desorption

  利用CO 2的化学固定来合成精细化学物质，是当今在绿色途径中利用温室气体CO 2的有吸引力的研究领域之一。一种花状银纳米颗粒接枝介孔氧化镁（AgNPs @ m-MgO）纳米复合材料已经通过一种简便的原位途径制备。通过XRD，FTIR，UV-vis，TG-DTA，FESEM，HR-TEM和N 2吸附-脱附研究对材料进行表征。该AgNPs @ m-MgO材料显示出具有良好表面积的介孔性质。这表明通过CO 2的化学固定，对末端炔烃的羧化反应都具有出色的催化活性。（1 atm）和在无溶剂条件下使用乙酸作为试剂对各种胺进行酰化反应，分别显示出分别高达98％和99％的丙酸和乙酰胺产品收率。该催化剂的可重复使用性也已得到验证，并且在两个反应中均显示出很高的再循环效率，并且没有明显的催化剂失活。
• 一种温和条件下制备丙炔酸及其衍生物的方 法
  申请人：中国科学院化学研究所

  公开号：CN108424367B

  公开（公告）日：2020-08-18

  本发明提供一种通过多米诺反应制备丙炔酸类化合物的新方法。所述方法为：在路易斯碱催化作用下，将端炔化合物与氢硅烷、CO2进行多米诺反应，得到丙炔酸类化合物。采用常用路易斯碱为促进剂，在温和条件下(40℃)，能高效地使端炔类化合物与氢硅烷和常压CO2反应生成相应的含有不同官能团的丙炔酸类化合物。该方法以CO2为原料，以便宜的路易斯碱为促进剂，避免贵金属的使用，采用多米诺反应，无需提纯和分离中间体，且反应条件温和，是一种高效、价廉的绿色合成方法，具有较强的工业应用价值。
• Carboxylation of terminal alkynes with CO₂ catalyzed by bis(amidate) rare-earth metal amides
  作者：Hao Cheng、Bei Zhao、Yingming Yao、Chengrong Lu

  DOI：10.1039/c4gc02200a

  日期：——

  Three novel bis(amidate) rare-earth metal amides were prepared and characterized. Treatment of CO₂ with terminal alkynes obtained propiolic acids in high to excellent yields using the highest reactive Nd-based catalyst at ambient pressure.

  三种新型双(酰胺)稀土金属酰胺已经制备并表征。在常压下，使用反应性最高的钕基催化剂处理CO2和末端炔烃，可以获得高至极好收率的丙炔酸。