propanedioic acid 1,3-phenylenebis(methylene) | 200133-24-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: propanedioic acid 1,3-phenylenebis(methylene)
• 英文别名: 3-[[3-[(2-Carboxyacetyl)oxymethyl]phenyl]methoxy]-3-oxopropanoic acid；3-[[3-[(2-carboxyacetyl)oxymethyl]phenyl]methoxy]-3-oxopropanoic acid
• CAS: 200133-24-0
• 化学式: C₁₄H₁₄O₈
• 分子量: 310.26
• InChiKey: GQHXXVNLPHBHBH-UHFFFAOYSA-N

物化性质

• 沸点：
  551.2±50.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-戊炔-1-醇 、 propanedioic acid 1,3-phenylenebis(methylene) 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到3-O-[[3-[(3-oxo-3-pent-4-ynoxypropanoyl)oxymethyl]phenyl]methyl] 1-O-pent-4-ynyl propanedioate
  参考文献：
  名称：

  Click chemistry with fullerene derivatives

  摘要：

  C(60) derivatives bearing either terminal alkyne or azide functional groups have been prepared and used as building blocks under the copper-mediated Huisgen 1,3-dipolar cycloaddition conditions leading to 1,2,3-triazole derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.064
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 1,3-苯二甲醇 反应 8.0h， 以99%的产率得到propanedioic acid 1,3-phenylenebis(methylene)
  参考文献：
  名称：

  富勒烯核上的大环化：[60]富勒烯的直接区域和非对映选择性多功能化，以及富勒烯-树枝状大分子衍生物的合成

  摘要：

  双重Bingel反应中的buckminsterfullerene，C 60和双丙二酸酯衍生物之间的大环化为制备具有高区域选择性和非对映选择性的C 60的共价双加合物提供了一种通用而简单的方法。光谱分析，立体化学因素和X射线晶体学的结合（图2）表明，在可能的进，出和出立体异构体中，双丙二酸酯的反应由o-联结，间-或对-亚二甲苯基系链仅提供外链式（方案1）。相反，使用衍生自1,10-菲咯啉的较大束缚物也提供了进出产品的第一个示例（±）-19（方案2）。从光学纯的双丙二酸酯衍生物开始，新的双官能化方法允许光学活性的富勒烯衍生物的非对映选择性制备（方案4和5），并最终实现了光学活性的顺式对映体的对映选择性制备（对映体过量ee> 97％）。3个双加合物，它们的手性完全由加成模式引起（图6）。具有光学活性的9,9'-spirobi [9 H]的双丙二酸酯的大环固定-芴]衍生的系绳至C 60下产生的24和耳鼻喉科-

  DOI：

  10.1002/hlca.19970800721

文献信息

• A fullerene core to probe dendritic shielding effects
  作者：Yannick Rio、Gianluca Accorsi、Hélène Nierengarten、Cyril Bourgogne、Jean-Marc Strub、Alain Van Dorsselaer、Nicola Armaroli、Jean-François Nierengarten

  DOI：10.1016/s0040-4020(03)00433-2

  日期：2003.5

  polarity (toluene, dichloromethane, acetonitrile). These data suggest a tighter core/periphery contact upon increase of solvent polarity and dendrimer size. In all the investigated solvents, the fullerene triplet lifetimes are steadily increased with the dendrimer volume, reflecting lower diffusion rates of O2 inside the dendrimers along the series. Measurements of quantum yields of singlet oxygen sensitization

  具有C 60核的树状聚合物是通过在碳球上环化树状双丙二酸酯衍生物而获得的。所得的双-甲基富勒烯衍生物已通过电喷雾（ES）和/或MALDI-TOF质谱法表征。在不同极性的溶剂（甲苯，二氯甲烷，乙腈）中，已经确定了UV-VIS吸收光谱，荧光光谱和富勒烯单态激发态寿命。这些数据表明，随着溶剂极性和树枝状聚合物尺寸的增加，核/外围接触更紧密。在所有研究的溶剂中，富勒烯三重态的寿命随树枝状聚合物的体积稳定增加，反映出O 2的扩散速率较低在树枝状聚合物中。对单线态氧敏化的量子产率的测量结果表明，寿命更长的三线态在二氯甲烷中产生的单线态氧（1 O 2 ∗）较少，但在非极性甲苯中则较少，这表明树枝状分支与CH 2 Cl 2中富勒烯核之间的接触更紧密。。在乙腈中，单线态氧产生的趋势是独特的。有效地，针对最大的树枝状聚合物监测单线态氧产生的增加。这反映出激发的1 O 2 ∗的特定相互作用 单重态氧寿命测量所探
• A DNA-Fullerene Conjugate as a Template for Supramolecular Chromophore Assemblies: Towards DNA-Based Solar Cells
  作者：Philipp Ensslen、Stefan Gärtner、Konstantin Glaser、Alexander Colsmann、Hans-Achim Wagenknecht

  DOI：10.1002/anie.201509332

  日期：2016.1.26

  template that serves as structural scaffold to self‐assemble an ordered and mixed array of ethynyl‐pyrene‐ and ethynyl‐Nile‐red‐nucleoside conjugates. Fluorescence spectroscopy revealed evidence for energy transfer between the two different chromophores. Moreover, fluorescence quenching is significantly enhanced by the attached fullerene in mixed assemblies of different chromophore ratios. This indicates

  富勒烯共价连接到（dA）20模板用作结构支架，以自组装乙炔基-re和乙炔基-尼罗尔-红-核苷结合物的有序和混合阵列。荧光光谱揭示了两种不同生色团之间能量转移的证据。此外，在不同生色团比率的混合组件中，附着的富勒烯可显着增强荧光猝灭作用。这表明通过电子从发色团堆叠上的光生激子转移到富勒烯，激子解离。富勒烯-DNA共轭物被集成为太阳能电池中的光敏层，在共轭物的所有三个成分的光谱范围内均显示出电荷载流子的产生。这项工作清楚地证明了DNA适合作为未来有机光电设备中发色团组装体的结构元素，
• Synthesis of fullerene building blocks bearing alkyne or azide groups and their subsequent functionalization by the copper mediated Huisgen 1,3-dipolar cycloaddition
  作者：Rossimiriam Pereira de Freitas、Julien Iehl、Béatrice Delavaux-Nicot、Jean-François Nierengarten

  DOI：10.1016/j.tet.2008.09.047

  日期：2008.12

  C-60 derivatives bearing either terminal alkyne or azide functional groups have been prepared and used as building blocks under the copper mediated Huisgen 1,3-dipolar cycloaddition conditions. In general, the reactivity of C60 toward azides does not significantly compete with the cycloaddition leading to the desired 1,2,3-triazole derivatives and good yields can be obtained when fullerene derivatives with reasonable Solubility are used as starting materials. The electrochemical properties of the new fullerene derivatives have also been investigated by cyclic voltammetry (CV) and Osteryoung Square Wave Voltammetry (OSWV). (C) 2008 Elsevier Ltd. All rights reserved.
• Amphiphilic Fullerene-Cholesterol Derivatives: Synthesis and Preparation ofLangmuir andLangmuir-Blodgett Films
  作者：Delphine Felder、Maria del Pilar Carreón、Jean-Louis Gallani、Daniel Guillon、Jean-François Nierengarten、Thierry Chuard、Robert Deschenaux

  DOI：10.1002/1522-2675(20010516)84:5<1119::aid-hlca1119>3.0.co;2-3

  日期：2001.5.16

  Amphiphilic fullerene bis-adducts 11 and 14 containing two and four cholesterol moieties, respectively, were prepared starting from the corresponding bis-malonate derivatives. In a systematic study, their spreading behavior at the air-water interface was compared to that of bis-adduct 6 with no polar head-group. Compared to 6, for which some three-dimensional aggregation occurs, the polar head-group in 11 and 14 is responsible for an attractive interaction with the aqueous subphase, forcing the molecules towards the water surface into a two-dimensional arrangement. Even if homogeneous Langmuir films were obtained with both 11 and 14, only the films of 14 show a reversible compression/expansion behavior. This suggests that, by increasing the number of cholesterol subunits, the encapsulation of the C-sphere in its addend is more efficient, thus preventing fullerene-fullerene interactions and aggregation phenomena. The Langmuir films of 11 and 14 were also efficiently transferred onto hydrophilic quartz slides, yielding Langmuir-Blodgett films.
• Macrocyclization on the fullerene core: Direct regio- and diastereoselective multi-functionalization of [60]fullerene, and synthesis of fullerene-dendrimer derivatives
  作者：Jean-François Nierengarten、Tilo Habicher、Roland Kessinger、Francesca Cardullo、François Diederich、Volker Gramlich、Jean-Paul Gisselbrecht、Corinne Boudon、Maurice Gross

  DOI：10.1002/hlca.19970800721

  日期：1997.11.3

  induce dramatic changes in the chiroptical properties of the tether chromophore such as strong enhancement and reversal of sign of the Cotton effects in the circular dichroism (CD) spectra (Figs. 4 and 5). By the same method, the functionafized bis-adducts 50 and 51 (Schemes 10 and 11) were prepared as initiator cores for the synthesis of the fullerene dendrimers 62, 63, and 66 (Schemes 12 and 13) by

  双重Bingel反应中的buckminsterfullerene，C 60和双丙二酸酯衍生物之间的大环化为制备具有高区域选择性和非对映选择性的C 60的共价双加合物提供了一种通用而简单的方法。光谱分析，立体化学因素和X射线晶体学的结合（图2）表明，在可能的进，出和出立体异构体中，双丙二酸酯的反应由o-联结，间-或对-亚二甲苯基系链仅提供外链式（方案1）。相反，使用衍生自1,10-菲咯啉的较大束缚物也提供了进出产品的第一个示例（±）-19（方案2）。从光学纯的双丙二酸酯衍生物开始，新的双官能化方法允许光学活性的富勒烯衍生物的非对映选择性制备（方案4和5），并最终实现了光学活性的顺式对映体的对映选择性制备（对映体过量ee> 97％）。3个双加合物，它们的手性完全由加成模式引起（图6）。具有光学活性的9,9'-spirobi [9 H]的双丙二酸酯的大环固定-芴]衍生的系绳至C 60下产生的24和耳鼻喉科-