(5-Bromopyridin-2-yl)methyl 2,2,2-trifluoroacetate | 900186-88-1

• 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
• 英文名称: (5-Bromopyridin-2-yl)methyl 2,2,2-trifluoroacetate
• 英文别名: (5-bromopyridin-2-yl)methyl 2,2,2-trifluoroacetate
• CAS: 900186-88-1
• 化学式: C₈H₅BrF₃NO₂
• 分子量: 284.032
• InChiKey: QHOASNPAVNSFRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5-Bromopyridin-2-yl)methyl 2,2,2-trifluoroacetate 在 甲醇 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (5-Bromopyridin-2-yl)methanol;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  WO2006/76415

  摘要：

  公开号：
• 作为产物：
  描述：

  2-甲基-5-溴吡啶-N-氧化物 、 三氟乙酸酐 反应 0.5h， 生成 (5-Bromopyridin-2-yl)methyl 2,2,2-trifluoroacetate
  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

• WO2006/76415
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.