4-(5-(6-(3-(ethylthio)phenyl)-2,2'-bipyridin-4-yl)thiophen-2-yl)-N,N-diphenylaniline | 1351823-50-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-(5-(6-(3-(ethylthio)phenyl)-2,2'-bipyridin-4-yl)thiophen-2-yl)-N,N-diphenylaniline
• 英文别名: 4-[5-[2-(3-ethylsulfanylphenyl)-6-pyridin-2-ylpyridin-4-yl]thiophen-2-yl]-N,N-diphenylaniline
• CAS: 1351823-50-1
• 化学式: C₄₀H₃₁N₃S₂
• 分子量: 617.838
• InChiKey: JDAKLDYKPFUERC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-乙酰基苯磺酰氯 在 四(三苯基膦)钯 、 ammonium acetate 、 水 、 碘 、 potassium carbonate 、 formamide 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 16.67h， 生成 4-(5-(6-(3-(ethylthio)phenyl)-2,2'-bipyridin-4-yl)thiophen-2-yl)-N,N-diphenylaniline
  参考文献：
  名称：

  Regioselective C–H Activation of Cyclometalated Bis-Tridentate Ruthenium Complexes

  摘要：

  A series of bis-tridentate Ru(II) complexes consisting of trimethyl-4,4',4"-tricarboxylate-2,2':6',2"-terpyridine (Me(3)tctpy) and derivatized 6-phenyl-2,2'-bipyridine (pbpy) ligands are reported. Each complex is attached to a terminal triphenylamine (TPA) substituent at the central ring of pbpy through a thiophene bridge to benefit light absorption, while the anionic ring of pbpy is fiinctionalized with substituents to modulate the metal-based redox potential. The cyclometalation step was found to favor the isomer where the electron-donating groups (EDGs; i.e., -OEt, -SEt) are situated ortho to the organometallic bond rather than the sterically favored para position, while the para isomer is formed in exclusivity when electron-withdrawing groups (e.g., -CF3,) are installed on the anionic ring. Moreover, the distribution of the isomeric products is affected by the identity of the chalcogen: ortho:para = 1:0 and 3:1 where EDG = -OEt and -SEt, respectively. Because our molecular scaffold rules out certain cyclometalation pathways (e.g., oxidative addition, agostic interactions, a-bond metathesis), we are able to experimentally establish that the observed regioselectivity is in accordance with an electrophilic metalation where the relative stabilities of the products and carbanionic intermediates govern the ratio of the isomers formed.

  DOI：

  10.1021/om200784j