5,7,8-trimethoxy-1,4-dihydro-1,4-methanonaphthalene-6-carboxylic acid methyl ester | 894763-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,7,8-trimethoxy-1,4-dihydro-1,4-methanonaphthalene-6-carboxylic acid methyl ester
• 英文别名: methyl 3,5,6-trimethoxytricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraene-4-carboxylate
• CAS: 894763-62-3
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: PLQBWPFKLHPEKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7,8-trimethoxy-1,4-dihydro-1,4-methanonaphthalene-6-carboxylic acid methyl ester 在 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 5,7,8-trimethoxy-1,4-dihydro-1,4-methanonaphthalene-6-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester
  参考文献：
  名称：

  Contrast Agents for Magnetic Resonance Imaging Synthesized with Ring-Opening Metathesis Polymerization

  摘要：

  A monomer for ring-opening metathesis polymerization (ROMP) has been developed that also functions as a portion of a GdIII chelating moiety for a magnetic resonance imaging contrast agent. An increase in per GdIII relaxivity was shown upon transition from monomer to polymer. Additionally, extremely large molecular relaxivities were achieved through incorporation of multiple GdIII ions per polymer. The nature of ROMP-derived polymers allows for functionalization of the monomer units and termini through orthogonal chemistry. This strategy is the basis for a new class of highly sensitive, targeted imaging agents.

  DOI：

  10.1021/ja061383p
• 作为产物：
  描述：

  7-methoxy-5,8-dioxo-1,4,4α,5,8,8α-hexahydro-1,4-methanonaphthalene-6-carboxylic acid methyl ester 、 硫酸二甲酯 在 氢氧化钾 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.0h， 以67%的产率得到5,7,8-trimethoxy-1,4-dihydro-1,4-methanonaphthalene-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Contrast Agents for Magnetic Resonance Imaging Synthesized with Ring-Opening Metathesis Polymerization

  摘要：

  A monomer for ring-opening metathesis polymerization (ROMP) has been developed that also functions as a portion of a GdIII chelating moiety for a magnetic resonance imaging contrast agent. An increase in per GdIII relaxivity was shown upon transition from monomer to polymer. Additionally, extremely large molecular relaxivities were achieved through incorporation of multiple GdIII ions per polymer. The nature of ROMP-derived polymers allows for functionalization of the monomer units and termini through orthogonal chemistry. This strategy is the basis for a new class of highly sensitive, targeted imaging agents.

  DOI：

  10.1021/ja061383p

文献信息

• Magnetic Resonance Imaging Contrast Agents Synthesized Using Ring-Opening Metathesis Polymerization
  申请人：Kiessling L. Laura

  公开号：US20080063602A1

  公开（公告）日：2008-03-13

  Polymeric chelating agents and metal chelates, particularly those of lanthanide metals and more specifically those of Gd(III), useful as contrast agents in magnetic resonance imaging (MRI) for therapeutic and diagnostic applications as well as clinical and biomedical research applications. The polymeric chelates are generated using ring-opening metathesis polymerization (ROMP). Polymers can have multiple sites for functionalization allowing for the synthesis of multimodal and targeted contrast agents. Hydroxypyridonate (HOPO)-based chelating moieties are integrated into a ROMP-derived polymer. More specifically, the HOPO-based chelating moiety is integrated into a benzonorbornadiene unit that constitutes the backbone of the polymer. The ROMP-derived polymer chelators can comprise multiple metal ions, particularly Gd(III) ions, in polymers of varying lengths to provide a series of agents with controlled relaxivites. Polymer chelates include those that are water-soluble.

  聚合螯合剂和金属螯合物，特别是镧系金属的螯合物，更具体地说是Gd（III）的螯合物，可用作磁共振成像（MRI）对比剂，用于治疗和诊断应用以及临床和生物医学研究应用。这些聚合螯合物是通过环烯烃开环聚合（ROMP）生成的。聚合物可以具有多个功能化位点，从而允许合成多模式和靶向对比剂。羟基吡啶酮（HOPO）基螯合基团被整合到ROMP衍生的聚合物中。更具体地说，HOPO基螯合基团被整合到构成聚合物骨架的苯并[2,3]环庚二烯单元中。ROMP衍生的聚合物螯合剂可以包括多个金属离子，特别是Gd（III）离子，在长度不同的聚合物中，以提供一系列具有可控松弛度的对比剂。聚合物螯合物包括水溶性的螯合物。
• Magnetic resonance imaging contrast agents synthesized using ring-opening metathesis polymerization
  申请人：Wisconsin Alumni Research Foundation

  公开号：US07807140B2

  公开（公告）日：2010-10-05

  Polymeric chelating agents and metal chelates, particularly those of lanthanide metals and more specifically those of Gd(III), useful as contrast agents in magnetic resonance imaging (MRI) for therapeutic and diagnostic applications as well as clinical and biomedical research applications. The polymeric chelates are generated using ring-opening metathesis polymerization (ROMP). Polymers can have multiple sites for functionalization allowing for the synthesis of multimodal and targeted contrast agents. Hydroxypyridonate (HOPO)-based chelating moieties are integrated into a ROMP-derived polymer. More specifically, the HOPO-based chelating moiety is integrated into a benzonorbornadiene unit that constitutes the backbone of the polymer. The ROMP-derived polymer chelators can comprise multiple metal ions, particularly Gd(III) ions, in polymers of varying lengths to provide a series of agents with controlled relaxivites. Polymer chelates include those that are water-soluble.

  聚合螯合剂和金属螯合物，特别是稀土金属的螯合物，更具体地说是Gd（III）的螯合物，在磁共振成像（MRI）中作为对比剂用于治疗和诊断应用以及临床和生物医学研究应用。聚合螯合物是使用环状开环重合聚合（ROMP）生成的。聚合物可以具有多个功能化位点，允许合成多模式和靶向对比剂。羟基吡啶酮（HOPO）基螯合基团被整合到ROMP衍生聚合物中。更具体地说，HOPO基螯合基团被整合到构成聚合物骨架的苯并[2,3]环庚二烯单元中。ROMP衍生的聚合物螯合剂可以包含多种金属离子，特别是Gd（III）离子，以控制弛豫效果提供一系列对比剂。聚合物螯合物包括水溶性的。
• US7807140B2
  申请人：——

  公开号：US7807140B2

  公开（公告）日：2010-10-05
• [EN] MAGNETIC RESONANCE IMAGING CONTRAST AGENTS SYNTHESIZED USING RING-OPENING METATHESIS POLYMERIZATION<br/>[FR] AGENTS DE CONTRASTE D'IMAGERIE PAR RÉSONANCE MAGNÉTIQUE, SYNTHÉTISÉS PAR POLYMÉRISATION PAR OUVERTURE DE CYCLE PAR MÉTATHÈSE
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2007131084A2

  公开（公告）日：2007-11-15

  [EN] Polymeric chelating agents and metal chelates, particularly those of lanthanide metals and more specifically those of Gd(III), useful as contrast agents in magnetic resonance imaging (MRI) for therapeutic and diagnostic applications as well as clinical and biomedical research applications. The polymeric chelates are generated using ring-opening metathesis polymerization (ROMP). Polymers can have multiple sites for functionalization allowing for the synthesis of multimodal and targeted contrast agents. Hydroxypyridonate (HOPO)-based chelating moieties are integrated into a ROMP-derived polymer. More specifically, the HOPO-based chelating moiety is integrated into a benzonorbornadiene unit that constitutes the backbone of the polymer. The ROMP-derived polymer chelators can comprise multiple metal ions, particularly Gd(III) ions, in polymers of varying lengths to provide a series of agents with controlled relaxivites. Polymer chelates include those that are water-soluble.
  [FR] L'invention concerne des chélateurs polymères et des chélates métalliques polymères, notamment ceux de métaux lanthanides et plus particulièrement ceux de Gd(III), pouvant servir d'agents de contraste dans l'imagerie par résonance magnétique (IRM) pour des applications thérapeutiques et diagnostiques ainsi que pour la recherche clinique et biomédicale. Les chélates polymères sont générés par polymérisation par ouverture de cycle par métathèse (ROMP). Des polymères peuvent avoir plusieurs sites de fonctionnalisation permettant la synthèse d'agents de contraste ciblés multimode. Des fragments chélateurs à base d'hydroxypyridonate (HOPO) sont intégrés dans un polymère dérivé par ROMP. De manière plus spécifique, le fragment chélateur à base d'HOPO est intégré dans une unité de benzonorbornadiène qui forme le squelette du polymère. Les chélateurs polymères dérivés par ROMP peuvent comprendre plusieurs ions de métal, en particulier des ions de Gd(III), dans des polymères de longueurs variables pour fournir une série d'agents à relaxivités contrôlées. Les chélates polymères comprennent les chélates hydrosolubles.
• Contrast Agents for Magnetic Resonance Imaging Synthesized with Ring-Opening Metathesis Polymerization
  作者：Matthew J. Allen、Ronald T. Raines、Laura L. Kiessling

  DOI：10.1021/ja061383p

  日期：2006.5.1

  A monomer for ring-opening metathesis polymerization (ROMP) has been developed that also functions as a portion of a GdIII chelating moiety for a magnetic resonance imaging contrast agent. An increase in per GdIII relaxivity was shown upon transition from monomer to polymer. Additionally, extremely large molecular relaxivities were achieved through incorporation of multiple GdIII ions per polymer. The nature of ROMP-derived polymers allows for functionalization of the monomer units and termini through orthogonal chemistry. This strategy is the basis for a new class of highly sensitive, targeted imaging agents.