双(5-溴-2-吡啶)甲酮 | 656828-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 双(5-溴-2-吡啶)甲酮
• 英文名称: bis(5-bromo-2-pyridinyl)methanone
• 英文别名: bis(5-bromopyridin-2-yl)methanone
• CAS: 656828-00-1
• 化学式: C₁₁H₆Br₂N₂O
• 分子量: 341.989
• InChiKey: IJJXZGQQYXFQSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 储存条件：
  储存条件：2-8°C，干燥且密封。

反应信息

• 作为反应物：
  描述：

  双(5-溴-2-吡啶)甲酮 在 吡啶 、 四(三苯基膦)钯 、 盐酸羟胺 、 sodium carbonate 、 乙二醇 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 68.0h， 生成 N-[bis(5-phenyl-2-pyridinyl)methyl]-N,N-bis[(5-phenyl-2-pyridinyl)methyl]amine
  参考文献：
  名称：

  Synthesis of a Non-Heme Template for Attaching Four Peptides:  An Approach to Artificial Iron(II)-Containing Peroxidases

  摘要：

  We are developing all-synthetic model cofactor-protein complexes in order to define the parameters controlling non-natural cofactor activity. The long-term objective is to establish the theoretical and practical basis for designing novel enzymes. A non-heme pentadentate ligand (N4Py) is being developed as a template for the site-specific attachment of a designed four-helix bundle. Previously, we attached two unprotected peptides via CH2Cl handles to N4Py. In the presence of hydrogen peroxide, the iron(II) complex of this ligand (2a) generates an (FeOOH)-O-III intermediate (3a) that can oxidize a wide variety of organic compounds. Here, we describe the synthesis of 27, a N4Py derivative in which four three-carbon spacers have been introduced, and show that four copies of an unprotected, single-cysteine peptide can be coupled via a thioether linkage to the ligand. In addition, a divergent synthesis route to tetrabromide ligand 1b has also been developed, providing the opportunity to prepare alternative pentadentate ligands efficiently by four cross-coupling reactions on a single molecule. Also, two of the four bromides of 1b can be selectively addressed by magnesium-bromide exchange.

  DOI：

  10.1021/jo035157z
• 作为产物：
  描述：

  2,5-二溴吡啶 、 碳酸二乙酯 在 正丁基锂 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.0h， 以37%的产率得到双(5-溴-2-吡啶)甲酮
  参考文献：
  名称：

  Synthesis of a Non-Heme Template for Attaching Four Peptides:  An Approach to Artificial Iron(II)-Containing Peroxidases

  摘要：

  We are developing all-synthetic model cofactor-protein complexes in order to define the parameters controlling non-natural cofactor activity. The long-term objective is to establish the theoretical and practical basis for designing novel enzymes. A non-heme pentadentate ligand (N4Py) is being developed as a template for the site-specific attachment of a designed four-helix bundle. Previously, we attached two unprotected peptides via CH2Cl handles to N4Py. In the presence of hydrogen peroxide, the iron(II) complex of this ligand (2a) generates an (FeOOH)-O-III intermediate (3a) that can oxidize a wide variety of organic compounds. Here, we describe the synthesis of 27, a N4Py derivative in which four three-carbon spacers have been introduced, and show that four copies of an unprotected, single-cysteine peptide can be coupled via a thioether linkage to the ligand. In addition, a divergent synthesis route to tetrabromide ligand 1b has also been developed, providing the opportunity to prepare alternative pentadentate ligands efficiently by four cross-coupling reactions on a single molecule. Also, two of the four bromides of 1b can be selectively addressed by magnesium-bromide exchange.

  DOI：

  10.1021/jo035157z

文献信息

• Synthesis of a Non-Heme Template for Attaching Four Peptides:  An Approach to Artificial Iron(II)-Containing Peroxidases
  作者：Marco van den Heuvel、Tieme A. van den Berg、Richard M. Kellogg、Christin T. Choma、Ben L. Feringa

  DOI：10.1021/jo035157z

  日期：2004.1.1

  We are developing all-synthetic model cofactor-protein complexes in order to define the parameters controlling non-natural cofactor activity. The long-term objective is to establish the theoretical and practical basis for designing novel enzymes. A non-heme pentadentate ligand (N4Py) is being developed as a template for the site-specific attachment of a designed four-helix bundle. Previously, we attached two unprotected peptides via CH2Cl handles to N4Py. In the presence of hydrogen peroxide, the iron(II) complex of this ligand (2a) generates an (FeOOH)-O-III intermediate (3a) that can oxidize a wide variety of organic compounds. Here, we describe the synthesis of 27, a N4Py derivative in which four three-carbon spacers have been introduced, and show that four copies of an unprotected, single-cysteine peptide can be coupled via a thioether linkage to the ligand. In addition, a divergent synthesis route to tetrabromide ligand 1b has also been developed, providing the opportunity to prepare alternative pentadentate ligands efficiently by four cross-coupling reactions on a single molecule. Also, two of the four bromides of 1b can be selectively addressed by magnesium-bromide exchange.