1,2,3-tris(methoxycarbonylmethoxy)benzene | 209909-16-0

• 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: 1,2,3-tris(methoxycarbonylmethoxy)benzene
• 英文别名: Trimethyl 2,2',2''-[benzene-1,2,3-triyltris(oxy)]triacetate；methyl 2-[2,3-bis(2-methoxy-2-oxoethoxy)phenoxy]acetate
• CAS: 209909-16-0
• 化学式: C₁₅H₁₈O₉
• 分子量: 342.303
• InChiKey: LXAOSRAHVGFFRK-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C(Solv: methanol (67-56-1))
• 沸点：
  421.6±40.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3-tris(methoxycarbonylmethoxy)benzene 在 dimethyl sulfide borane 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 180.5h， 生成 [4-(2-Allyloxy-ethoxy)-17-benzoyl-6,7,9,10,12,13,16,17,18,19-decahydro-15H-5,11,14,20-tetraoxa-8,17-diaza-benzocyclooctadecen-8-yl]-phenyl-methanone
  参考文献：
  名称：

  A new strategy for the synthesis of pendant benzodiazacoronands and their use as components of chromatographic stationary phases

  摘要：

  The synthesis of a novel class of functionalized benzophanes in which a (2'-hydroxy)ethoxy pendant arm is attached to the phenyl ring is reported. The reported approach, utilizes simple starting materials, and skillful organization of the synthetic steps allows for simultaneous transforms of the macrocyclic ring and the pendant arm. Binding studies of these systems with Pd2+ and Cd2+ cations is described. A chromatographic stationary phase containing the benzodiazacoronand moiety was also synthesized, and found to interact specifically with isomeric nitrobenzene derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.012
• 作为产物：
  描述：

  溴乙酸甲酯 、 邻苯三酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以60%的产率得到1,2,3-tris(methoxycarbonylmethoxy)benzene
  参考文献：
  名称：

  Synthesis and properties of potassium salts of per-O-carboxymethyl-calix[4]pyrogallols and their complexes with Cu2+, Fe3+, and La3+

  摘要：

  描述了杯[4]连苯三酚羧甲基衍生物的水溶性钾盐和十二(羧基甲基)四甲基杯[4]连苯三酚(L)与过渡金属离子(Cu2+、Fe3+、La3+)络合物的合成。通过核磁共振波谱、ESR 和红外光谱对它们的固态和溶液结构进行了表征。杯[4]连苯三酚十二甲酸酯以 rccc 构型存在。下缘带有甲基取代基的杯[4]连苯三酚以多种浓度存在于水中，主要以二聚体形式存在。所得多核过渡金属配合物具有比杯[4]连苯三酚钾盐(K12L)更不对称的结构。所有研究的复合物都含有通过相当强的氢键结合的水分子。在室温下，Fe4L 配合物的特征是 Fe3+ 离子的环境接近八面体。 Cu6L 复合物的 ESR 光谱中没有信号表明 Cu2+-Cu2+ 存在强反铁磁相互作用。

  DOI：

  10.1007/s11172-009-0012-8

文献信息

• The use of tris(2-aminoethyl)amine in macrocyclization processes
  作者：Piotr Lipkowski、Daniel T. Gryko、Janusz Jurczak、Janusz Lipkowski

  DOI：10.1016/s0040-4039(98)00624-8

  日期：1998.5

  Reactions of tripodal amine 1 with tripodal esters 2 and 4, carried out in methanol under ambient conditions, afforded - as single products - tricyclic cryptands 3 and 5, respectively. Under the same conditions, the amine 1 reacted with dipodal esters 6 and 7 to give bis-macrocycles 9 and 10, respectively. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• A new strategy for the synthesis of pendant benzodiazacoronands and their use as components of chromatographic stationary phases
  作者：Piotr Piątek、Daniel T Gryko、Agnieszka Szumna、Janusz Jurczak

  DOI：10.1016/j.tet.2004.05.012

  日期：2004.6

  The synthesis of a novel class of functionalized benzophanes in which a (2'-hydroxy)ethoxy pendant arm is attached to the phenyl ring is reported. The reported approach, utilizes simple starting materials, and skillful organization of the synthetic steps allows for simultaneous transforms of the macrocyclic ring and the pendant arm. Binding studies of these systems with Pd2+ and Cd2+ cations is described. A chromatographic stationary phase containing the benzodiazacoronand moiety was also synthesized, and found to interact specifically with isomeric nitrobenzene derivatives. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and properties of potassium salts of per-O-carboxymethyl-calix[4]pyrogallols and their complexes with Cu2+, Fe3+, and La3+
  作者：S. N. Podyachev、S. N. Sudakova、V. V. Syakaev、N. E. Burmakina、R. R. Shagidullin、V. I. Morozov、L. V. Avvakumova、A. I. Konovalov

  DOI：10.1007/s11172-009-0012-8

  日期：2009.1

  Synthesis of water-soluble potassium salts of carboxymethyl derivatives of calix[4]pyrogallols and dodeca(carboxylatomethyl)tetramethylcalix[4]pyrogallol (L) complexes with transition metal ions (Cu2+, Fe3+, La3+) is described. Their structures in the solid state and in solution were characterized by NMR spectroscopy, ESR, and IR spectroscopy. Calix[4]pyrogallol dodecacarboxylates exist in the rccc-configuration. Calix[4]pyrogallol with methyl substituents at the lower rim in a wide range concentrations exists in water predominantly in the dimeric form. The obtained polynuclear transition metal complexes possess less symmetric structure than potassium salt of calix[4]pyrogallol (K12L). All studied complexes contain water molecules bound by rather strong hydrogen bonds. At room temperature the Fe4L complex is characterized by the environment of the Fe3+ ions close to octahedral. The absence of signals in the ESR spectrum of the Cu6L complex indicates the strong antiferromagnetic interaction Cu2+-Cu2+.

  描述了杯[4]连苯三酚羧甲基衍生物的水溶性钾盐和十二(羧基甲基)四甲基杯[4]连苯三酚(L)与过渡金属离子(Cu2+、Fe3+、La3+)络合物的合成。通过核磁共振波谱、ESR 和红外光谱对它们的固态和溶液结构进行了表征。杯[4]连苯三酚十二甲酸酯以 rccc 构型存在。下缘带有甲基取代基的杯[4]连苯三酚以多种浓度存在于水中，主要以二聚体形式存在。所得多核过渡金属配合物具有比杯[4]连苯三酚钾盐(K12L)更不对称的结构。所有研究的复合物都含有通过相当强的氢键结合的水分子。在室温下，Fe4L 配合物的特征是 Fe3+ 离子的环境接近八面体。 Cu6L 复合物的 ESR 光谱中没有信号表明 Cu2+-Cu2+ 存在强反铁磁相互作用。