1,3-di-o-tolylphenanthreno[9,10-d]imidazol-2-ylidene | 1148009-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,3-di-o-tolylphenanthreno[9,10-d]imidazol-2-ylidene
• 英文别名: 1,3-bis(2-methylphenyl)-2H-phenanthro[9,10-d]imidazol-3-ium-2-ide
• CAS: 1148009-71-5
• 化学式: C₂₉H₂₂N₂
• 分子量: 398.507
• InChiKey: JXSALLYGVGSUAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  silver hexafluoroantimonate 、 1,3-di-o-tolylphenanthreno[9,10-d]imidazol-2-ylidene 以 四氢呋喃 为溶剂， 以66%的产率得到bis(1,3-di-o-tolylphenanthreno[9,10-d]imidazol-2-ylidene)silver hexafluoroantimonate
  参考文献：
  名称：

  Annulated N-Heterocyclic Carbenes: 1,3-Ditolylphenanthreno[9,10-d]imidazol-2-ylidene and Transition Metal Complexes Thereof

  摘要：

  The N,N'-bis(tolylamino)phenanthrenes 1a and 1b were synthesized by reductive cyclization of benzil-bis(tolylimines) and cyclized with triethyl orthoformate in the presence of NH4PF6 to give the corresponding bis(tolyl)phenanthreno[9,10-d]imidazolium hexafluorophosphates 2a,b. These were deprotonated with excess KH in THE Whereas the p-tolyl-substituted phenanthrene-annulated imidazol-2-ylidene (phenimy) 3a proved to be unstable and dimerized to 4a, the bulkier o-tolyl derivative is isolable as the monomer carbene 3b. Cationic silver complexes were prepared by the method of Wang and Lin (6a, 6b) or directly (6b), rhodium and palladium complexes 7b-9b by reaction of 3b and the respective metal precursors. Detailed structural information is given by X-ray crystal structure analyses of 6a and 7b and by HH- and CH-COSY NMR measurements of 1b, 2a, 2b, 3b, and 7b, representing the various compound types. The phenimy ligands are distinguished from benzo- or linear naphtho-annulated imidazol-2-ylidene ligands by higher basicity and free 3b by lower deshielding of the C-13(II) nuclei.

  DOI：

  10.1021/om9000132