1-(3-nitrobenzyl)-4,8,11-tris[(6-bromo-2,2'-bipyridine-5'-yl)methyl]-1,4,8,11-tetraazacyclotetradecane | 439614-41-2

• 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: 1-(3-nitrobenzyl)-4,8,11-tris[(6-bromo-2,2'-bipyridine-5'-yl)methyl]-1,4,8,11-tetraazacyclotetradecane
• 英文别名: 1,4,8-Tris[[6-(6-bromopyridin-2-yl)pyridin-3-yl]methyl]-11-[(3-nitrophenyl)methyl]-1,4,8,11-tetrazacyclotetradecane
• CAS: 439614-41-2
• 化学式: C₅₀H₅₀Br₃N₁₁O₂
• 分子量: 1076.73
• InChiKey: ZCKSJTYJOFULFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  66
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-(3-nitrobenzyl)-4,8,11-tris[(6-bromo-2,2'-bipyridine-5'-yl)methyl]-1,4,8,11-tetraazacyclotetradecane 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 1-(3-nitrobenzyl)-4,8,11-tris[(6-carboxy-2,2'-bipyridine-5'-yl)methyl]-1,4,8,11-tetraazacyclotetradecane
  参考文献：
  名称：

  5‘-Substituted-6-carboxylic-2,2‘-bipyridine Acid:  A Pivotal Architecton for Building Preorganized Ligands

  摘要：

  A set of ligands bearing 6-bromo-2,2'-bipyridine pendant arms attached in the 5'-position are described. Trans formation of the bromo to an ester was performed by a carboethoxylation reaction promoted by low-valent Pd(0), while saponification followed by acidification gave the acids. The introduction of an appended function 3-nitrobenzyl, benzamidomethyl, and tert-butylacetyl opens the way to further functionalize these scaffolds for potential labeling of biological material. The synthetic protocols represent a valuable approach to the rational design of ligands bearing oxophilic and anionic sidearms.

  DOI：

  10.1021/jo0200015
• 作为产物：
  描述：

  1,4,8,11-四氮杂环十四烷 在 sodium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 72.67h， 生成 1-(3-nitrobenzyl)-4,8,11-tris[(6-bromo-2,2'-bipyridine-5'-yl)methyl]-1,4,8,11-tetraazacyclotetradecane
  参考文献：
  名称：

  5‘-Substituted-6-carboxylic-2,2‘-bipyridine Acid:  A Pivotal Architecton for Building Preorganized Ligands

  摘要：

  A set of ligands bearing 6-bromo-2,2'-bipyridine pendant arms attached in the 5'-position are described. Trans formation of the bromo to an ester was performed by a carboethoxylation reaction promoted by low-valent Pd(0), while saponification followed by acidification gave the acids. The introduction of an appended function 3-nitrobenzyl, benzamidomethyl, and tert-butylacetyl opens the way to further functionalize these scaffolds for potential labeling of biological material. The synthetic protocols represent a valuable approach to the rational design of ligands bearing oxophilic and anionic sidearms.

  DOI：

  10.1021/jo0200015