1-(3-nitrobenzyl)-4,8,11-tris[(6-carboethoxy-2,2'-bipyridine-5'-yl)methyl]-1,4,8,11-tetraazacyclotetradecane | 439614-42-3

• 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-carboethoxy-2,2'-bipyridine-5'-yl)methyl]-1,4,8,11-tetraazacyclotetradecane
• 英文别名: Ethyl 6-[5-[[4,8-bis[[6-(6-ethoxycarbonylpyridin-2-yl)pyridin-3-yl]methyl]-11-[(3-nitrophenyl)methyl]-1,4,8,11-tetrazacyclotetradec-1-yl]methyl]pyridin-2-yl]pyridine-2-carboxylate
• CAS: 439614-42-3
• 化学式: C₅₉H₆₅N₁₁O₈
• 分子量: 1056.23
• InChiKey: PTJULZOPDLHQJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  78
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  215
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1-(3-nitrobenzyl)-4,8,11-tris[(6-carboethoxy-2,2'-bipyridine-5'-yl)methyl]-1,4,8,11-tetraazacyclotetradecane 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以83%的产率得到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 bis-triphenylphosphine-palladium(II) chloride sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 72.67h， 生成 1-(3-nitrobenzyl)-4,8,11-tris[(6-carboethoxy-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

文献信息

• 5‘-Substituted-6-carboxylic-2,2‘-bipyridine Acid:  A Pivotal Architecton for Building Preorganized Ligands
  作者：Loïc J. Charbonnière、Nicolas Weibel、Raymond F. Ziessel

  DOI：10.1021/jo0200015

  日期：2002.5.1

  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.