N,N'-bis[2-(3-{2-[(3-bromophenyl)amino]ethyl}adamantan-1-yl)ethyl]benzene-1,3-diamine | 1211463-33-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis[2-(3-{2-[(3-bromophenyl)amino]ethyl}adamantan-1-yl)ethyl]benzene-1,3-diamine
• 英文别名: N,N'-bis(2-{3-[2-(3-bromophenylamino)ethyl]adamantan-1-yl}ethyl)benzene-1,3-diamine；N,N'-bis[2-(3-{2-[(3-bromophenyl)amino]ethyl}-adamantan-1-yl)ethyl]benzene-1,3-diamine；1-N,3-N-bis[2-[3-[2-(3-bromoanilino)ethyl]-1-adamantyl]ethyl]benzene-1,3-diamine
• CAS: 1211463-33-0
• 化学式: C₄₆H₆₀Br₂N₄
• 分子量: 828.817
• InChiKey: NUJYKMVLTWVCEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二溴苯 、 1,3-金刚烷二乙胺 在 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以39%的产率得到3-bromo-N-(2-{3-[2-(3-bromophenylamino)ethyl]adamantan-1-yl}ethyl)aniline
  参考文献：
  名称：

  Arylation of adamantanamines: III. Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine

  摘要：

  Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2'-(adamantane-1,3-diyl)diethanamine with isomeric bromochloro- and dibromobenzenes was studied. The yields of N,N'-diarylation products depend on the initial diamine and dihalobenzene structure. Side reactions were revealed, which reduced the yield of the target products. The arylation of 2,2'-(adamantane-1,3-diyl) diethanamine gives the corresponding N,N'-diaryl derivatives with better yield. The possibility for synthesizing unsymmetrical N, N'-diaryl derivatives of 2,2'-(adamantane-1,3-diyl) diethanamine was demonstrated.

  DOI：

  10.1134/s1070428011010027

文献信息

• Palladium-catalyzed amination in the synthesis of macrocyclic compounds containing 1,3-disubstituted adamantane fragments
  作者：E. R. Ranyuk、A. D. Averin、A. K. Buryak、E. N. Savel’ev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428009100236

  日期：2009.10

  Palladium-catalyzed amination of 1,3-dibromobenzene, 2,6-dibromopyridine, 3,3'-dibromobiphenyl, 2,7-dibromonaphthalene, and 1,8-dichloroanthracene with an equimolar amount of 2,2'-(adamantane-1,3-diyl)diethanamine resulted in the formation of macrocyclic compounds containing one or several adamantane and one or several aromatic fragments. The reactions of 2,2'-(adamantane-1,3-diyl)diethanamine with excess 1,3-dibromobenzene, 2,6-dibromopyridine, 1,8-dichloroanthracene, and 1,8-dichloroanthraquinone gave the corresponding N,N'-diaryl derivatives. Polyaza macrocycles incorporating adamantane, aromatic, and 4,7,10-trioxatridecane-1,13-diamine fragments, were obtained by palladium-catalyzed amination of the N,N'-diaryl derivatives with 4,7,10-trioxatridecane-1,13-diamine.