2,5-bis(allyloxy)terephthalic acid | 149590-60-3

• 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: 2,5-bis(allyloxy)terephthalic acid
• 英文别名: 2,5-bis(prop-2-enoxy)terephthalic acid
• CAS: 149590-60-3
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: XQJAVEMHUDLYIT-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174 °C
• 沸点：
  484.3±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,5-bis(allyloxy)terephthalic acid 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 2,5-dihydroxy-1-N,4-N-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]benzene-1,4-dicarboxamide
  参考文献：
  名称：

  Chiral Benzoquinones as a New Class of Ligands for Asymmetric Catalysis:  Synthesis and Application to the Palladium(II)-Catalyzed 1,4-Dialkoxylation of 1,3-Dienes

  摘要：

  Chiral C-2-symmetric 2,5-bisamide hydroquinone ligands, with beta-amino alcohols as chiral building units, were synthesized in excellent overall yields. The ligands gave up to 54.4% ee in the palladium-catalyzed 1,4-dialkoxylation of 1,3-dienes. These findings demonstrate the potential of asymmetric induction utilizing chiral benzoquinones as ligands in palladium(II) catalysis, albeit with modest enantiomeric excesses. Weakly coordinating hydroxyl groups of the ligand appear to be crucial for the success of the reaction. Mechanistic aspects and the origin of enantioselectivity are also discussed.

  DOI：

  10.1021/jo980561x
• 作为产物：
  描述：

  2,5-二羟基对苯二甲酸乙酯 在 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2,5-bis(allyloxy)terephthalic acid
  参考文献：
  名称：

  Chiral Benzoquinones as a New Class of Ligands for Asymmetric Catalysis:  Synthesis and Application to the Palladium(II)-Catalyzed 1,4-Dialkoxylation of 1,3-Dienes

  摘要：

  Chiral C-2-symmetric 2,5-bisamide hydroquinone ligands, with beta-amino alcohols as chiral building units, were synthesized in excellent overall yields. The ligands gave up to 54.4% ee in the palladium-catalyzed 1,4-dialkoxylation of 1,3-dienes. These findings demonstrate the potential of asymmetric induction utilizing chiral benzoquinones as ligands in palladium(II) catalysis, albeit with modest enantiomeric excesses. Weakly coordinating hydroxyl groups of the ligand appear to be crucial for the success of the reaction. Mechanistic aspects and the origin of enantioselectivity are also discussed.

  DOI：

  10.1021/jo980561x

文献信息

• Functional tolerance in an isoreticular series of highly porous metal–organic frameworks
  作者：Min Kim、Jake A. Boissonnault、Corinne A. Allen、Phuong V. Dau、Seth M. Cohen

  DOI：10.1039/c2dt30120b

  日期：——

  A series of highly porous University of Michigan Crystalline Material (UMCM-1) type Zn-based metal–organic frameworks (MOFs) were synthesized from mono- and bi-functionalized benzenedicarboxylate (BDC) ligands. In total, 16 new functionalized UMCM-1 derivatives were obtained by a combination of pre- and postsynthetic functionalization. Through postsynthetic modification (PSM), amino–halo bifunctional

  从单官能和双官能化的苯二甲酸（BDC）配体合成了一系列高度多孔的密歇根大学结晶材料（UMCM-1）型锌基金属有机骨架（MOF）。通过合成前和合成后的功能化，总共获得了16种新的功能化UMCM-1衍生物。通过后期合成修饰（PSM），氨基-卤代双功能MOF通过固态酰化反应转化为酰胺-卤代材料。一系列包含Cl，Br和I基团的双功能MOF显示，PSM转化不受卤化物大小的影响，仅受这些固态有机转化中所用试剂的空间体积的影响。
• A Robust Mixed‐Lanthanide PolyMOF Membrane for Ratiometric Temperature Sensing
  作者：Tongtong Feng、Yingxiang Ye、Xiao Liu、Hui Cui、Zhiqiang Li、Ying Zhang、Bin Liang、Huanrong Li、Banglin Chen

  DOI：10.1002/anie.202009765

  日期：2020.11.23

  Temperature sensors play a significant role in biology, chemistry, and engineering, especially those that can work accurately in a noninvasive manner. We adopted a photoinduced post‐synthetic copolymerization strategy to realize a membranous ratiometric luminescent thermometer based on the emissions of two lanthanide ions. This novel mixed‐lanthanide polyMOF membrane exhibits not only the integrity

  温度传感器在生物学，化学和工程学中起着重要作用，尤其是那些可以以无创方式准确工作的传感器。我们采用了光诱导的合成后共聚策略，以基于两个镧系元素离子的排放量实现膜比例发光温度计。这种新型的混合镧系元素聚MOF膜不仅具有Ln-MOF粉末的完整性和温度感应性能，而且还具有出色的机械性能，例如柔韧性，弹性和可加工性。此外，polyMOF膜在苛刻的条件下也表现出出色的稳定性，包括高湿度，强酸和强碱（pH 0-14），可在极端情况下绘制温度分布图。
• Directing the Breathing Behavior of Pillared-Layered Metal–Organic Frameworks via a Systematic Library of Functionalized Linkers Bearing Flexible Substituents
  作者：Sebastian Henke、Andreas Schneemann、Annika Wütscher、Roland A. Fischer

  DOI：10.1021/ja302991b

  日期：2012.6.6

  Implementation of two differently functionalized linkers in varying ratios yields multicomponent single-phased [Zn(2)(fu-bdc')(2x)(fu-bdc″)(2-2x)(dabco)](n) MOFs (0 < x < 1) of increased inherent complexity, which feature a non-linear dependence of their gas sorption properties on the applied ratio of components. Hence, the responsive behavior of such pillared-layered MOFs can be extensively tuned

  柔性金属有机骨架 (MOF)，也称为软多孔晶体 (SPC)，显示出取决于吸附客体分子的性质和数量的可逆结构转变。在最近的研究中，据报道有机接头的共价功能化可以影响甚至整合 MOF 中的框架灵活性（“呼吸”）。然而，对这种响应特性的合理微调是非常可取的，但也具有挑战性。在这里，我们提出了一种强大的方法，用于基于母体结构 [Zn(2)(bdc)(2)(dabco)](n) (bdc = 1,4-苯二羧酸酯；dabco = 1,4-二氮杂双环[2.2.2]辛烷）。功能化 bdc 型链接器 (fu-bdc) 库，在苯核的不同位置带有额外的悬挂侧基（具有不同官能度和极性的不同链长的烷氧基）。材料 [Zn(2)(fu-bdc)(2)(dabco)](n) 的合成产生了高响应 MOF 的相应集合。母 MOF 的灵活性很弱；然而，[Zn(2)(fu-bdc)(2)(dabco)](n) 的取代骨架在客体去除后急剧收缩，并在吸附
• Post-synthetic pore-space expansion in a di-tagged metal–organic framework
  作者：Lodey Tshering、Sally O. Hunter、Alexandra Nikolich、Erica Minato、Christopher M. Fitchett、Deanna M. D'Alessandro、Christopher Richardson

  DOI：10.1039/c4ce01377h

  日期：——

  A rarely observed example of post-synthetically increasing pore space, while retaining the chemical functionality of the original metal–organic framework is reported. Conventional solvothermal heating in air was used to effect an efficient post-synthetic rearrangement of a bisallyloxy-tagged zinc metal–organic framework. This leads to the pore-space expanded MOF displaying a higher surface area yet lower affinity for CO2 sorption compared to the original MOF.

  本报告报道了一个罕见的例子，即在保留原始金属有机框架化学功能的同时，通过合成后方法增加孔隙空间。通过在空气中进行传统的溶解热加热，对双烯丙基氧基标记的锌金属有机框架进行了有效的合成后重排。这使得孔隙空间扩大的 MOF 与原始 MOF 相比，表面积更大，但二氧化碳吸附亲和力更低。
• A Covalent and Modular Synthesis of Homo- and Hetero[<i>n</i>]rotaxanes
  作者：Milo D. Cornelissen、Simone Pilon、Luuk Steemers、Martin J. Wanner、Steven Frölke、Ed Zuidinga、Steen Ingemann Jørgensen、Jarl Ivar van der Vlugt、Jan H. van Maarseveen

  DOI：10.1021/acs.joc.9b03030

  日期：2020.3.6

  30-membered all-carbon macrocycle provides access to a modular series of rotaxanes. Installment of tethered alkynes or azides onto the terephthalic phenolic hydroxyl functionalities, which are situated at opposite sides of the macrocycle, gives versatile prerotaxane building blocks. The corresponding [2]rotaxanes are obtained by introduction of bulky stoppering ("capping") units at the tethers and subsequent

  在30元全碳大环的轴上掺入2,5-二羟基对苯二酸酯作为共价支架，可提供一系列模块化的轮烷。将拴系的炔烃或叠氮化物安装在对苯二甲酸酚羟基官能团上，对苯酚羟基官能团位于大环的相对侧，可提供通用的轮烷构筑物。相应的[2]轮烷是通过在系链上引入大的塞子（“封端”）单元并随后裂解共价环/线酯键而获得的。通过偶联具有互补连接子功能的两种前轮烷烷（即叠氮化物和炔烃）和后续的塞基连接，可以扩展对这一策略的有效利用。通过合成一系列[2]-，[3]-和[4]轮烷，证明了这种新颖方法的适用性和模块化性质。此外，显示出前轮烷允许环片段的后期功能化，从而引入进一步的结构多样性。