3-(1,3-dioxan-2-yl)-2-hydroxy-5-iodobenzoic acid | 685870-22-8

• 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-(1,3-dioxan-2-yl)-2-hydroxy-5-iodobenzoic acid
• CAS: 685870-22-8
• 化学式: C₁₁H₁₁IO₅
• 分子量: 350.11
• InChiKey: GEJCUPPZKLUBBR-UHFFFAOYSA-N

物化性质

• 沸点：
  402.9±45.0 °C(Predicted)
• 密度：
  1.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1,3-dioxan-2-yl)-2-hydroxy-5-iodobenzoic acid 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.05h， 生成 3-(4,4'-dimethoxytrityloxy)prop-1-yl 2-benzoyloxy-3-(1,3-dioxan-2-yl)-5-iodobenzoate
  参考文献：
  名称：

  Synthesis of Linear and Tripoidal Oligo(phenylene ethynylene)-Based Building Blocks for Application in Modular DNA-Programmed Assembly

  摘要：

  Rigid linear and tripoidal organic modules based on the oligo(phenylene ethynylene) backbone having salicylaldehyde-derived termini are synthesized. A highly functionalized 5-iodosalicyl aldehyde was prepared and coupled to each ethynyl group of 1,4-diethynylbenzene or 1,3,5-triethynylbenzene in Sonogashira couplings. The two or three termini of the compounds are functionalized for incorporation in linear and branched oligonucleotide strands. For the linear module (LM), the two termini are equipped with amide spacers, and one of these was functionalized with a DMTr (dimethoxytrityl)-protected hydroxy group and the other with a phosphoramidite. One of the tripoidal modules is prepared with DMTr groups in two of its three termini. A tripoidal module is also synthesized with three different groups on its hydroxy termini: a phosphoramidite, a DMTr group, and an Fmoc group. Extended studies have shown that these rigid linear and tripoidal organic modules can be incorporated into short oligonucleotides. Several of these modules can be applied for DNA-directed assembly and covalent coupling into structures of predetermined connectivity. Such structures have potential application for molecular electronics and nanotechnology.

  DOI：

  10.1021/jo035764m
• 作为产物：
  描述：

  5-碘水杨酸 在 硫酸 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 21.0h， 生成 3-(1,3-dioxan-2-yl)-2-hydroxy-5-iodobenzoic acid
  参考文献：
  名称：

  Synthesis of Linear and Tripoidal Oligo(phenylene ethynylene)-Based Building Blocks for Application in Modular DNA-Programmed Assembly

  摘要：

  Rigid linear and tripoidal organic modules based on the oligo(phenylene ethynylene) backbone having salicylaldehyde-derived termini are synthesized. A highly functionalized 5-iodosalicyl aldehyde was prepared and coupled to each ethynyl group of 1,4-diethynylbenzene or 1,3,5-triethynylbenzene in Sonogashira couplings. The two or three termini of the compounds are functionalized for incorporation in linear and branched oligonucleotide strands. For the linear module (LM), the two termini are equipped with amide spacers, and one of these was functionalized with a DMTr (dimethoxytrityl)-protected hydroxy group and the other with a phosphoramidite. One of the tripoidal modules is prepared with DMTr groups in two of its three termini. A tripoidal module is also synthesized with three different groups on its hydroxy termini: a phosphoramidite, a DMTr group, and an Fmoc group. Extended studies have shown that these rigid linear and tripoidal organic modules can be incorporated into short oligonucleotides. Several of these modules can be applied for DNA-directed assembly and covalent coupling into structures of predetermined connectivity. Such structures have potential application for molecular electronics and nanotechnology.

  DOI：

  10.1021/jo035764m

文献信息

• Synthesis of functional molecular rod oligomers
  作者：Casper S. Andersen、Kurt V. Gothelf

  DOI：10.1039/b815099k

  日期：——

  We are presenting the synthesis of a phenylene ethynylene-based rod containing an Fmoc protected amino group and an activated acid which can be applied to peptide couplings. This linear amino acid analogue is applied to the synthesis of di-, tri- and pentamers. The pentamer has a molecular mass of 6.5 kDa and is characterized by 1H NMR spectroscopy and MALDI-TOF MS. The method has potential for the

  我们提出了一种含有Fmoc保护的氨基和可用于肽偶联的活化酸的亚苯基乙炔基棒的合成。该线性氨基酸类似物用于二，三和五聚体的合成。五聚体的分子量为6.5 kDa，并通过1 H NMR光谱和MALDI-TOF MS进行表征。该方法具有形成长大分子低聚物的潜力。
• [EN] MACROMOLECULAR ARCHITECTURES<br/>[FR] ARCHITECTURES MACROMOLECULAIRES
  申请人：UNIV AARHUS

  公开号：WO2004050231A2

  公开（公告）日：2004-06-17

  A macromolecular architecture suitable for use in molecular electronics. And in the manufacture of conductors and semi-conductors has been synthesised using linear and branched oligomers of organic molecules. The incorporation of a bi-or tri-functional organic compound in an oligonucleotide chain and the application of these for formation of covalently linked organic and metal-organic oligomers has led to a novel molecular architecture. Furthermore, the iterative serial synthesis of linear and branched organic oligomers by automated methods such as DNA-synthesis or peptide synthesis, using bi- or tri-functional organic monomers is described herein. The novel compounds may be used to position and arrange nanoscale substrates such as biomolecules, biological structures, colloids, supramolecular structures forming covalently linked assemblies for use as conducting wires and components in electronic devices.