N-[bis[5-(3-bromopropyl)-2-pyridinyl]methyl]-N,N-bis[[5-(3-bromopropyl)-2-pyridinyl]methyl]amine | 656827-99-5

• 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: N-[bis[5-(3-bromopropyl)-2-pyridinyl]methyl]-N,N-bis[[5-(3-bromopropyl)-2-pyridinyl]methyl]amine
• 英文别名: 1,1-bis[5-(3-bromopropyl)pyridin-2-yl]-N,N-bis[[5-(3-bromopropyl)pyridin-2-yl]methyl]methanamine
• CAS: 656827-99-5
• 化学式: C₃₅H₄₁Br₄N₅
• 分子量: 851.36
• InChiKey: GUGANINCPZKVBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetylamino-3-mercapto-propionic acid methyl ester 、 N-[bis[5-(3-bromopropyl)-2-pyridinyl]methyl]-N,N-bis[[5-(3-bromopropyl)-2-pyridinyl]methyl]amine 在 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以9.5 mg的产率得到methyl 2-acetamido-3-[3-[6-[[[5-[3-(2-acetamido-3-methoxy-3-oxopropyl)sulfanylpropyl]pyridin-2-yl]methyl-[bis[5-[3-(2-acetamido-3-methoxy-3-oxopropyl)sulfanylpropyl]pyridin-2-yl]methyl]amino]methyl]pyridin-3-yl]propylsulfanyl]propanoate
  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-溴-5-醛基吡啶 在 乙酸铵 、 manganese(IV) oxide 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 盐酸羟胺 、 sodium hydride 、 caesium carbonate 、 triphenylphosphine dibromide 1:1 addition complex 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 133.76h， 生成 N-[bis[5-(3-bromopropyl)-2-pyridinyl]methyl]-N,N-bis[[5-(3-bromopropyl)-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