methyl 3-(3,4,5-trihydroxyphenyl)propionate | 883196-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl 3-(3,4,5-trihydroxyphenyl)propionate
• 英文别名: Methyl 3-(3,4,5-trihydroxyphenyl)propanoate；methyl 3-(3,4,5-trihydroxyphenyl)propanoate
• CAS: 883196-20-1
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: UUKIMUFRHZBAJF-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C(Solv: ethyl acetate (141-78-6); chloroform (67-66-3))
• 沸点：
  413.5±40.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(3,4,5-trihydroxyphenyl)propionate 在 lithium aluminium tetrahydride 、 四溴化碳 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 3-(3,4,5-triheptyloxyphenyl)propylbromide
  参考文献：
  名称：

  通过树枝状苝双酰亚胺的动力学控制自组装产生的自修复复杂螺旋柱

  摘要：

  最近有报道称树枝状苝 3,4:9,10-四羧酸双酰亚胺 (PBI), (3,4,5)12G1-3-PBI 可在含有 PBI 四聚体作为基本重复单元的复杂螺旋柱中自组装. 这些四聚体包含一对并排排列的两个分子，另一对在柱的下一层中颠倒并围绕柱轴旋转。四聚体内和四聚体间的旋转角度和堆叠距离是不同的。在高温下，(3,4,5)12G1-3-PBI 通过热力学控制过程在 2D 六角柱状相中自组装，而在低温下通过动力学控制过程在 3D 正交柱状阵列中自组装。在这里，我们通过差示扫描量热法、X 射线和电子衍射的组合报告了合成和结构分析，和固态核磁共振在不同温度下对由 (3,4,5)nG1-3-PBI 库生成的超分子结构进行，n = 14-4。对于 n = 11-8，来自低温的动力学控制自组装在热力学控制过程中发生变化，而 n = 9 和 8 的正交柱状阵列从热力学产物转变为动力学产物。n = 9, 8

  DOI：

  10.1021/ja208501d
• 作为产物：
  描述：

  没食子酸丙酯 在 palladium on activated charcoal 吗啉 、 lithium aluminium tetrahydride 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 methyl 3-(3,4,5-trihydroxyphenyl)propionate
  参考文献：
  名称：

  Synthesis and Retrostructural Analysis of Libraries of AB₃ and Constitutional Isomeric AB₂ Phenylpropyl Ether-Based Supramolecular Dendrimers

  摘要：

  We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 35-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy)phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3,4-bis[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl-1-propyl-, and 3-13,4,5-tris[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyllpropyI ether first-generation clendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from clendritic dipepticles and hollow supramolecular spheres were also discovered from these building blocks. The more flexible and less compact 3-phenylpropyl ether repeat units are stable under acidic conditions, facilitate a simpler synthetic strategy, provide faster dynamics of self-assembly into higher-order supramolecular structures of larger dimensions, exhibit lower transition temperatures than the corresponding benzyl ether homologues, and demonstrate the generality of the self-assembly concept based on amphiphilic dendrons.

  DOI：

  10.1021/ja060062a

文献信息

• Self-Assembly of Dendronized Perylene Bisimides into Complex Helical Columns
  作者：Virgil Percec、Mihai Peterca、Timur Tadjiev、Xiangbing Zeng、Goran Ungar、Pawaret Leowanawat、Emad Aqad、Mohammad R. Imam、Brad M. Rosen、Umit Akbey、Robert Graf、Sivakumar Sekharan、Daniel Sebastiani、Hans W. Spiess、Paul A. Heiney、Steven D. Hudson

  DOI：10.1021/ja204366b

  日期：2011.8.10

  The synthesis of perylene 3,4:9,10-tetracarboxylic acid bisimides (PBIs) dendronized with first-generation dendrons containing 0 to 4 methylenic units (m) between the imide group and the dendron, (3,4,5)12G1-m-PBI, is reported. Structural analysis of their self-organized arrays by DSC, X-ray diffraction, molecular modeling, and solid-state (1)H NMR was carried out on oriented samples with heating and

  苝 3,4:9,10-四羧酸双酰亚胺 (PBI) 的合成与第一代树枝状化合物在酰亚胺基团和树枝状化合物之间含有 0 到 4 个亚甲基单元 (m)，(3,4,5)12G1-报告了 m-PBI。通过 DSC、X 射线衍射、分子建模和固态 (1)H NMR 对其自组织阵列的结构分析是在加热和冷却速率为 20 至 0.2 °C/min 的定向样品上进行的。在高温下，(3,4,5)12G1-m-PBI 自组装成柱内有序的二维六边形柱状相。在低温下，它们形成具有 3D 周期性的正交 (m = 0, 2, 3, 4) 和单斜 (m = 1) 柱状阵列。正交相具有接近六边形的对称性。对于 m = 0, 2, 3, 4 ，它们由四聚体作为基本单元组成。四聚体包含一对并排排列的两个分子，另一对位于柱的下一层，倒置并围绕柱轴以不同角度旋转以用于不同的 m。相反，对于 m = 1，每个层中只有一个分子，具有四层 2(1)
• Increasing 3D Supramolecular Order by Decreasing Molecular Order. A Comparative Study of Helical Assemblies of Dendronized Nonchlorinated and Tetrachlorinated Perylene Bisimides
  作者：Benjamin E. Partridge、Pawaret Leowanawat、Emad Aqad、Mohammad R. Imam、Hao-Jan Sun、Mihai Peterca、Paul A. Heiney、Robert Graf、Hans W. Spiess、Xiangbing Zeng、Goran Ungar、Virgil Percec

  DOI：10.1021/jacs.5b02147

  日期：2015.4.22

  tetrachlorinated perylene bisimide (Cl4PBI) was functionalized with two AB3 minidendrons containing hydrogenated or semifluorinated dodecyl groups. The hydrogenated dendron was attached to the imide groups of Cl4PBI via m = 0, 1, and 2 methylenic units, whereas the dendron containing semifluorinated groups was attached via m = 3 or a di(ethylene oxide) linker (m = 2EO). The supramolecular structures of these

  一种非平面的、扭曲的、柔性的四氯化苝双酰亚胺 (Cl4PBI) 被两个含有氢化或半氟化十二烷基的 AB3 小树枝官能化。氢化树突通过 m = 0、1 和 2 亚甲基单元连接到 Cl4PBI 的酰亚胺基团，而含有半氟化基团的树突通过 m = 3 或二（环氧乙烷）接头（m = 2EO）连接。这些化合物的超分子结构由差示扫描量热法、X 射线衍射和固态 NMR 的组合确定，与之前报道的非氯化平面和刚性 PBI 的结构进行了比较，这证明了二维周期阵列的热力学控制形成在高温和低温下的 3D 阵列。在 m = 0 和 2 的热力学控制下，分子较少有序的 Cl4PBI 包含氢化树枝状分子自组织成专门的 3D 晶体周期阵列，而较高分子有序的 PBI 产生不太稳定和有序的 3D 晶体以及 2D 组件。这种在不太有序的分子构建块的超分子组装中诱导更高程度的 3D 有序是出乎意料的。m = 3 的半氟化树枝状 Cl4PBI
• Complex Columnar Hexagonal Polymorphism in Supramolecular Assemblies of a Semifluorinated Electron-Accepting Naphthalene Bisimide
  作者：Yu-Chun Wu、Pawaret Leowanawat、Hao-Jan Sun、Benjamin E. Partridge、Mihai Peterca、Robert Graf、Hans W. Spiess、Xiangbing Zeng、Goran Ungar、Chain-Shu Hsu、Paul A. Heiney、Virgil Percec

  DOI：10.1021/ja510643b

  日期：2015.1.21

  Simple synthetic methods for a strongly electron-accepting naphthalene bisimide (NBI) derivative functionalized with a new environmentally friendly chiral racemic semifluorinated alkyl group and with AB(3) minidendrons containing the same semifluorinated group are reported. The semifluorinated dendron was attached to the imide groups of the NBI via one, two, and three (m = 1, 2, 3) methylenic units. The NBI-containing semifluorinated groups and the dendronized NBI with m = 1 and 2 self-organize into lamellar crystals. The dendronized NBI with m = 3 self-assembles into an unprecedentedly complex and ordered column that self-organizes in a columnar hexagonal periodic array. This array undergoes a continuous transition to a columnar hexagonal superlattice that does not display a first-order phase transition during analysis by differential scanning calorimetry at heating and cooling rates of 10 and 1 degrees C/min. These complex columnar hexagonal periodic arrays with intramolecular order could be elucidated only by a combination of powder and fiber X-ray diffraction studies and solid-state NMR experiments. The lamellar crystals self-organized from m = 1 and the two highly ordered columnar hexagonal periodic arrays of m = 3 are assembled via thermodynamically controlled processes. Since strongly electron-accepting derivatives are of great interest to replace fullerene acceptors in organic photovoltaics and for other supramolecular electronic materials, the multitechnique structural analysis methodology elaborated here must be taken into consideration in all related studies.
• Self-Repairing Complex Helical Columns Generated via Kinetically Controlled Self-Assembly of Dendronized Perylene Bisimides
  作者：Virgil Percec、Steven D. Hudson、Mihai Peterca、Pawaret Leowanawat、Emad Aqad、Robert Graf、Hans W. Spiess、Xiangbing Zeng、Goran Ungar、Paul A. Heiney

  DOI：10.1021/ja208501d

  日期：2011.11.16

  The dendronized perylene 3,4:9,10-tetracarboxylic acid bisimide (PBI), (3,4,5)12G1-3-PBI, was recently reported to self-assemble in complex helical columns containing tetramers of PBI as basic repeat unit. These tetramers contain a pair of two molecules arranged side-by-side and another pair in the next stratum of the column turned upside-down and rotated around the column axis. Intra- and intertetramer

  最近有报道称树枝状苝 3,4:9,10-四羧酸双酰亚胺 (PBI), (3,4,5)12G1-3-PBI 可在含有 PBI 四聚体作为基本重复单元的复杂螺旋柱中自组装. 这些四聚体包含一对并排排列的两个分子，另一对在柱的下一层中颠倒并围绕柱轴旋转。四聚体内和四聚体间的旋转角度和堆叠距离是不同的。在高温下，(3,4,5)12G1-3-PBI 通过热力学控制过程在 2D 六角柱状相中自组装，而在低温下通过动力学控制过程在 3D 正交柱状阵列中自组装。在这里，我们通过差示扫描量热法、X 射线和电子衍射的组合报告了合成和结构分析，和固态核磁共振在不同温度下对由 (3,4,5)nG1-3-PBI 库生成的超分子结构进行，n = 14-4。对于 n = 11-8，来自低温的动力学控制自组装在热力学控制过程中发生变化，而 n = 9 和 8 的正交柱状阵列从热力学产物转变为动力学产物。n = 9, 8
• Synthesis and Retrostructural Analysis of Libraries of AB₃ and Constitutional Isomeric AB₂ Phenylpropyl Ether-Based Supramolecular Dendrimers
  作者：Virgil Percec、Mihai Peterca、Monika J. Sienkowska、Marc A. Ilies、Emad Aqad、Jan Smidrkal、Paul A. Heiney

  DOI：10.1021/ja060062a

  日期：2006.3.1

  We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 35-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy)phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3,4-bis[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl-1-propyl-, and 3-13,4,5-tris[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyllpropyI ether first-generation clendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from clendritic dipepticles and hollow supramolecular spheres were also discovered from these building blocks. The more flexible and less compact 3-phenylpropyl ether repeat units are stable under acidic conditions, facilitate a simpler synthetic strategy, provide faster dynamics of self-assembly into higher-order supramolecular structures of larger dimensions, exhibit lower transition temperatures than the corresponding benzyl ether homologues, and demonstrate the generality of the self-assembly concept based on amphiphilic dendrons.