2-carbomethoxy-4-methoxy-9-bromomethyl-1,10-phenanthroline | 916907-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-carbomethoxy-4-methoxy-9-bromomethyl-1,10-phenanthroline
• 英文别名: Methyl 9-(bromomethyl)-4-methoxy-1,10-phenanthroline-2-carboxylate
• CAS: 916907-31-8
• 化学式: C₁₆H₁₃BrN₂O₃
• 分子量: 361.195
• InChiKey: MKLBOFPGTKVCKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-carbomethoxy-4-methoxy-9-bromomethyl-1,10-phenanthroline 、 DL-谷氨酸二甲酯盐酸盐 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 42.0h， 以65%的产率得到2-carbomethoxy-4-methoxy-9-methoxymethyl-1,10-phenanthroline
  参考文献：
  名称：

  Stepwise Construction of Polysubstituted Phenanthroline-Based Glutamate Pockets for Lanthanide Complexation

  摘要：

  我们设计出了一种基于谷氨酸骨架的多功能配体，它含有菲罗啉羧基单元作为发色团和螯合臂。在 2-羰基甲氧基-4-甲氧基-9-溴甲基-1,10-菲罗啉结构单元的基础上，通过碱辅助双 N-烷基化谷氨酸二甲酯盐酸盐，再经过皂化步骤，就得到了目标配体的四盐酸盐。在 pH 值为 7.0 的 0.01 M TRIS/HCl 水缓冲液中，研究了配体及其镧系元素（III）配合物的光谱特性。铕（III）配合物具有很强的发光能力，尽管在第一配位层中存在约一分子水，其量子产率仍高达 6%；而铽（III）配合物的发光能力很弱。

  DOI：

  10.1055/s-2006-942533
• 作为产物：
  描述：

  8-氨基喹哪啶 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 作用下， 以 甲醇 、 二苯醚 、 乙腈 、 苯 为溶剂， 反应 39.83h， 生成 2-carbomethoxy-4-methoxy-9-bromomethyl-1,10-phenanthroline
  参考文献：
  名称：

  Stepwise Construction of Polysubstituted Phenanthroline-Based Glutamate Pockets for Lanthanide Complexation

  摘要：

  我们设计出了一种基于谷氨酸骨架的多功能配体，它含有菲罗啉羧基单元作为发色团和螯合臂。在 2-羰基甲氧基-4-甲氧基-9-溴甲基-1,10-菲罗啉结构单元的基础上，通过碱辅助双 N-烷基化谷氨酸二甲酯盐酸盐，再经过皂化步骤，就得到了目标配体的四盐酸盐。在 pH 值为 7.0 的 0.01 M TRIS/HCl 水缓冲液中，研究了配体及其镧系元素（III）配合物的光谱特性。铕（III）配合物具有很强的发光能力，尽管在第一配位层中存在约一分子水，其量子产率仍高达 6%；而铽（III）配合物的发光能力很弱。

  DOI：

  10.1055/s-2006-942533

文献信息

• Lanthanide Complexes Preparation and Uses Thereof
  申请人：Charbonniere Loic

  公开号：US20080044923A1

  公开（公告）日：2008-02-21

  The invention relates to compounds, to the complexes they form with a lanthanide, and to the use of the complexes for fluorescence marking or NMR imaging. The complex consists of an Ln ion and a ligand R 2 -C(X-R 1 )(R 3 )-NR 4 R 5 . R 1 is a functional group, X is a single bond or a hydrocarbon-based chain consisting of at least one alkylene or alkenylene group optionally comprising at least one hetero atom or an arylene. R 2 is an anionic group A 2 or a C 1 -C 4 alkylene or alkenylene group bearing at least one such group A 2 and optionally comprising at least one hetero atom. R 3 is H or a C 1 -C 5 alkylene or alkenylene group optionally containing at least one hetero atom, and optionally bearing at least one anionic group A 3 . R 4 is a substituent with light-absorbing properties that forms chelate rings with Ln. R 5 is a substituent that forms chelate rings with Ln.
• Lanthanide Complexes, Preparation and Uses Thereof
  申请人：Charbonniere Loïc

  公开号：US20100216252A1

  公开（公告）日：2010-08-26

  The invention relates to compounds, to the complexes they form with a lanthanide, and to the use of the complexes for fluorescence marking or NMR imaging. The complex consists of an Ln ion and a ligand R 2 —C(X—R 1 )(R 3 )—NR 4 R 5 . R 1 is a functional group, X is a single bond or a hydrocarbon-based chain consisting of at least one alkylene or alkenylene group optionally comprising at least one hetero atom or an arylene. R 2 is an anionic group A 2 or a C 1 -C 4 alkylene or alkenylene group bearing at least one such group A 2 and optionally comprising at least one hetero atom. R 3 is H or a C 1 -C 5 alkylene or alkenylene group optionally containing at least one hetero atom, and optionally bearing at least one anionic group A 3 . R 4 is a substituent with light-absorbing properties that forms chelate rings with Ln. R 5 is a substituent that forms chelate rings with Ln.
• US7709263B2
  申请人：——

  公开号：US7709263B2

  公开（公告）日：2010-05-04
• US7838299B2
  申请人：——

  公开号：US7838299B2

  公开（公告）日：2010-11-23
• Stepwise Construction of Polysubstituted Phenanthroline-Based Glutamate Pockets for Lanthanide Complexation
  作者：Raymond Ziessel、Loïc Charbonnière、Nicolas Weibel

  DOI：10.1055/s-2006-942533

  日期：——

  A multi-functionalized ligand, based on a glutamic acid skeleton, bearing phenanthroline carboxylic units as chromophores and chelating arms has been designed. A base-assisted bis N-al­kylation of dimethyl glutamate hydrochloride with the pivotal 2-carbomethoxy-4-methoxy-9-bromomethyl-1,10-phenanthroline building block, followed by a saponification step, provided the target ligand as its tetrahydrochloride salt. The spectroscopic properties of the ligand and its lanthanide(III) complexes were investigated in aqueous 0.01 M TRIS/HCl buffer at pH 7.0. The europium(III) complex was highly luminescent, exhibiting a quantum yield of 6% despite the presence of ca. one molecule of water in the first coordination sphere, whereas the terbium(III) complex was only weakly luminescent.

  我们设计出了一种基于谷氨酸骨架的多功能配体，它含有菲罗啉羧基单元作为发色团和螯合臂。在 2-羰基甲氧基-4-甲氧基-9-溴甲基-1,10-菲罗啉结构单元的基础上，通过碱辅助双 N-烷基化谷氨酸二甲酯盐酸盐，再经过皂化步骤，就得到了目标配体的四盐酸盐。在 pH 值为 7.0 的 0.01 M TRIS/HCl 水缓冲液中，研究了配体及其镧系元素（III）配合物的光谱特性。铕（III）配合物具有很强的发光能力，尽管在第一配位层中存在约一分子水，其量子产率仍高达 6%；而铽（III）配合物的发光能力很弱。