5-Ethyl-2-(4-methylphenyl)-3,3-diphenyl-1,2,4-oxadiazole | 1354486-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Ethyl-2-(4-methylphenyl)-3,3-diphenyl-1,2,4-oxadiazole
• 英文别名: 5-ethyl-2-(4-methylphenyl)-3,3-diphenyl-1,2,4-oxadiazole
• CAS: 1354486-24-0
• 化学式: C₂₃H₂₂N₂O
• 分子量: 342.44
• InChiKey: JNFAFFKKCFIYCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [PdCl₂{N=C(Et)ON(C₆H₄Me-p)CPh₂}₂] 、 1,2-双(二苯基膦)乙烷 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Pd(1,2-bis(diphenylphosphino)ethane)2Cl2 、 5-Ethyl-2-(4-methylphenyl)-3,3-diphenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  A Palladium(II) Center Activates Nitrile Ligands toward 1,3-Dipolar Cycloaddition of Nitrones Substantially More than the Corresponding Platinum(II) Center

  摘要：

  Palladium(II)-coordinated NCR1 (R-1 = Et (1), NMe2 (2), Ph (3)) species react smoothly with acyclic nitrones such as the ketonitrones Ph2C=N(O)R-4 (R-4 = p-MeC6H4 (4), p-ClC6H4 (5)) and the aldonitrone p-MeC6H4CH=N(O)Me (6) in the corresponding nitrile media. This reaction proceeds as a consecutive two-step intermolecular cycloaddition to give the mono- and bis-2,3-dihydro-1,2,4-oxadiazole complexes [PdCl2((RCN)-C-1){N-a=C (R-1) ON (R-4)C-b((RR3)-R-2)}}((a-b)) (7a-13a; R-2, R-3 = Ph; R-4 = C6H4Me-p, R-1 = Et (7), NMe2 (8), Ph (9); R4 = C6H4C1-p, = Et (10), NMe2 (11), Ph (12); R2 = H, R-3 = C6H4Me-p, R-4 = Me, R-1 = NMe2 (13)) and [PdCl2{Na= C(R-1)ON(R-4)Cb((RR3)-R-2)}(2)]((a-b)) (7b-13b), respectively. Inspection of the obtained data and their comparison with the previous results indicate that the Pd-II centers provide substantially greater activation of RCN ligands toward the 1,3-dipolar cycloaddition than the relevant Pt-II centers. The palladium(II)-mediated 1,3-dipolar cycloaddition of ketonitrones to nitriles is reversible. All complexes were characterized by elemental analyses (C, H, N), high-resolution ESI-MS, and IR and H-1 and C-13{H-1} NMR spectroscopy. The structure of trans7b was determined by single-crystal X-ray diffraction. Metal-free 5-NR'2-2,3-dihydro-1,2,4-oxadiazoles (7c-13c) were liberated from the corresponding (2,3-dihydro-1,2,4-oxadiazole)2Pd(II) complexes by treatment with 1,2-(diphenylphosphino)ethane, and the heterocycles were characterized by high-resolution ESI+-MS and H-1 and 13C{IFI} spectroscopy.

  DOI：

  10.1021/ic301866y

文献信息

• A Palladium(II) Center Activates Nitrile Ligands toward 1,3-Dipolar Cycloaddition of Nitrones Substantially More than the Corresponding Platinum(II) Center
  作者：Andreii S. Kritchenkov、Nadezhda A. Bokach、Galina L. Starova、Vadim Yu. Kukushkin

  DOI：10.1021/ic301866y

  日期：2012.11.5

  Palladium(II)-coordinated NCR1 (R-1 = Et (1), NMe2 (2), Ph (3)) species react smoothly with acyclic nitrones such as the ketonitrones Ph2C=N(O)R-4 (R-4 = p-MeC6H4 (4), p-ClC6H4 (5)) and the aldonitrone p-MeC6H4CH=N(O)Me (6) in the corresponding nitrile media. This reaction proceeds as a consecutive two-step intermolecular cycloaddition to give the mono- and bis-2,3-dihydro-1,2,4-oxadiazole complexes [PdCl2((RCN)-C-1)N-a=C (R-1) ON (R-4)C-b((RR3)-R-2)}}((a-b)) (7a-13a; R-2, R-3 = Ph; R-4 = C6H4Me-p, R-1 = Et (7), NMe2 (8), Ph (9); R4 = C6H4C1-p, = Et (10), NMe2 (11), Ph (12); R2 = H, R-3 = C6H4Me-p, R-4 = Me, R-1 = NMe2 (13)) and [PdCl2Na= C(R-1)ON(R-4)Cb((RR3)-R-2)}(2)]((a-b)) (7b-13b), respectively. Inspection of the obtained data and their comparison with the previous results indicate that the Pd-II centers provide substantially greater activation of RCN ligands toward the 1,3-dipolar cycloaddition than the relevant Pt-II centers. The palladium(II)-mediated 1,3-dipolar cycloaddition of ketonitrones to nitriles is reversible. All complexes were characterized by elemental analyses (C, H, N), high-resolution ESI-MS, and IR and H-1 and C-13H-1} NMR spectroscopy. The structure of trans7b was determined by single-crystal X-ray diffraction. Metal-free 5-NR'2-2,3-dihydro-1,2,4-oxadiazoles (7c-13c) were liberated from the corresponding (2,3-dihydro-1,2,4-oxadiazole)2Pd(II) complexes by treatment with 1,2-(diphenylphosphino)ethane, and the heterocycles were characterized by high-resolution ESI+-MS and H-1 and 13CIFI} spectroscopy.