2,7-Bis(methoxycarbonylmethoxy)naphtalene | 201042-06-0

• 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: 2,7-Bis(methoxycarbonylmethoxy)naphtalene
• 英文别名: methyl 2-[7-(2-methoxy-2-oxoethoxy)naphthalen-2-yl]oxyacetate
• CAS: 201042-06-0
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: HQWXLKNFDJSIJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,7-Bis(methoxycarbonylmethoxy)naphtalene 在 一水合肼 作用下， 以 甲醇 为溶剂， 以492 mg的产率得到2,2'-(naphthalene-2,7-diylbis(oxy))diacetohydrazide
  参考文献：
  名称：

  Screening of π-Basic Naphthalene and Anthracene Amplifiers for π-Acidic Synthetic Pore Sensors

  摘要：

  Synthetic ion channels and pores attract current attention as multicomponent sensors in complex matrixes. This application requires the availability of reactive signal amplifiers that covalently capture analytes and drag them into the pore. pi-Basic 1,5-dialkoxynaphthalenes (1,5-DAN) are attractive amplifiers because aromatic electron donor-acceptor (AEDA) interactions account for their recognition within pi-acidic naphthalenediimide (NDI) rich synthetic pores. Focusing on amplifier design, we report here the synthesis of a complete collection of DAN and dialkoxyanthracene amplifiers, determine their oxidation potentials by cyclic voltammetry, and calculate their quadrupole moments. Blockage experiments reveal that subtle structural changes in regioisomeric DAN amplifiers can be registered within NDI pores. Frontier orbital overlap in AEDA complexes, oxidation potentials, and, to a lesser extent, quadrupole moments are shown to contribute to isomer recognition by synthetic pores. Particularly important with regard to practical applications of synthetic pores as multianalyte sensors, we further demonstrate that application of the lessons learned with DAN regioisomers to the expansion to dialkoxyanthracenes provides access to privileged amplifiers with submicromolar activity.

  DOI：

  10.1021/ja078256t
• 作为产物：
  描述：

  2,7-二羟基萘 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以78%的产率得到2,7-Bis(methoxycarbonylmethoxy)naphtalene
  参考文献：
  名称：

  钯催化偶联修饰氨基酸衍生物的侧链

  摘要：

  据报道，钯催化的芳基卤化物和三氟甲磺酸酯与炔丙基氨基酰胺的偶合以及芳基和乙烯基卤化物和三氟甲磺酸酯与乙炔基恶唑烷的偶合。

  DOI：

  10.1016/s0040-4020(97)10197-1

文献信息

• Elaboration of the side-chain of amino acid derivatives by palladium catalysed couplings
  作者：Geoffrey T. Crisp、Yu-Lin Jiang、Peter J. Pullman、Chris De Savi

  DOI：10.1016/s0040-4020(97)10197-1

  日期：1997.12

  The palladium-catalysed couplings of aryl halides and triflates with propargyl amino amides and the couplings of aryl and vinyl halides and triflates with an ethynyl oxazolidine are reported.

  据报道，钯催化的芳基卤化物和三氟甲磺酸酯与炔丙基氨基酰胺的偶合以及芳基和乙烯基卤化物和三氟甲磺酸酯与乙炔基恶唑烷的偶合。
• Screening of π-Basic Naphthalene and Anthracene Amplifiers for π-Acidic Synthetic Pore Sensors
  作者：Shinya Hagihara、Ludovic Gremaud、Guillaume Bollot、Jiri Mareda、Stefan Matile

  DOI：10.1021/ja078256t

  日期：2008.4.1

  Synthetic ion channels and pores attract current attention as multicomponent sensors in complex matrixes. This application requires the availability of reactive signal amplifiers that covalently capture analytes and drag them into the pore. pi-Basic 1,5-dialkoxynaphthalenes (1,5-DAN) are attractive amplifiers because aromatic electron donor-acceptor (AEDA) interactions account for their recognition within pi-acidic naphthalenediimide (NDI) rich synthetic pores. Focusing on amplifier design, we report here the synthesis of a complete collection of DAN and dialkoxyanthracene amplifiers, determine their oxidation potentials by cyclic voltammetry, and calculate their quadrupole moments. Blockage experiments reveal that subtle structural changes in regioisomeric DAN amplifiers can be registered within NDI pores. Frontier orbital overlap in AEDA complexes, oxidation potentials, and, to a lesser extent, quadrupole moments are shown to contribute to isomer recognition by synthetic pores. Particularly important with regard to practical applications of synthetic pores as multianalyte sensors, we further demonstrate that application of the lessons learned with DAN regioisomers to the expansion to dialkoxyanthracenes provides access to privileged amplifiers with submicromolar activity.
• Dynamic Combinatorial Donor−Acceptor Catenanes in Water: Access to Unconventional and Unexpected Structures
  作者：Ho Yu Au-Yeung、G. Dan Pantoş、Jeremy K. M. Sanders

  DOI：10.1021/jo101981p

  日期：2011.3.4

  describe here the assembly of new types of donor−acceptor [2]catenanes from dynamic combinatorial libraries (DCL) in water. These new catenanes contain both the donor and acceptor components in at least one of the interlocked rings, thereby possessing unusual and unexpected DAAD or DADD stacking sequences of the π units in their structures. The efficiency of the catenane assembly process can be enhanced

  我们在这里描述了从水中的动态组合库（DCL）组装新型供体-受体[2]邻苯二酚的过程。这些新的链烯在至少一个互锁的环中同时含有供体和受体成分，从而在其结构中具有异常和意外的DAAD或DADD堆积序列。可以通过多种方式操纵DCL平衡来提高链烷烃组装过程的效率：添加客体，改变构件的化学计量比或增加库浓度或溶剂的离子强度。发现链烷的形成及其组成取决于供体构件的几何形状，尺寸和柔韧性的细微差异。