[Pd(o-C6H4CH=CNC(O)OCPh)(CH3C(O)CHC(O)CH3)] | 1214747-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [Pd(o-C6H4CH=CNC(O)OCPh)(CH3C(O)CHC(O)CH3)]
• CAS: 1214747-31-5
• 化学式: C₂₁H₁₇NO₄Pd
• 分子量: 453.79
• InChiKey: YJVJUPCCRMOLQC-LVDFRVDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  [Pd(μ-OAc)(o-C6H4CH=CNC(O)OCPh)]2 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 [Pd(o-C6H4CH=CNC(O)OCPh)(CH3C(O)CHC(O)CH3)]
  参考文献：
  名称：

  通过 CH 键激活对 GFP 样荧光团进行正畸：范围和光物理特性

  摘要：

  CH 和 EPU 感谢 CA15106 资助下的欧洲科学技术合作 (COST) 计划：有机合成中的 CH 激活 (CHAOS)。AIJ、CC 和 EPU 感谢Ministryio de Economia y Competitividad MINECO（西班牙，CTQ2013-40855R 项目）和 Gobierno de Aragon-FEDER（西班牙，研究组 E19_17R：Aminoacidos y Peptidos）提供的资金支持。这项工作得到了鲁昂大学、鲁昂国家应用科学研究院 (INSA Rouen)、国家科学研究中心 (CNRS)、卓越实验室 (Labex) SynOrg 和诺曼底地区的部分支持。

  DOI：

  10.1002/ejoc.201800966

文献信息

• Ortho-Palladation of (<i>Z</i>)-2-Aryl-4-Arylidene-5(4<i>H</i>)-Oxazolones. Structure and Functionalization
  作者：Gheorghe-Doru Roiban、Elena Serrano、Tatiana Soler、Maria Contel、Ion Grosu、Carlos Cativiela、Esteban P. Urriolabeitia

  DOI：10.1021/om901068f

  日期：2010.3.22

  Ortho-palladated complexes of (Z)-2-aryl-4-arylidene-5(4H)-oxazolones have been prepared through oxidative addition. The reaction of (Z)-2-phenyl-4-(2-bromobenzylidene)-5(4H)-oxazolone (4) with Pd-2(dba)(3)center dot CHCl3 gives the six-membered cyclopalladated dinuclear complex [Pd(mu-Br)(o-C6H4CH=CNC(O)OCPh)](2) (7). The reaction of 7 with PPh3 gives dinuclear 9, which incorporates one phosphine per Pd atom through cleavage of the Pd-N bond, and preserves the bromide bridging system. However, reaction with PPh2Me gives mononuclear 8, which incorporates two phosphines as a results of the cleavage of the mu-Br system and N displacement. In contrast, the reaction of 7 with pyridine gives complex 12 due to Simple cleavage of the Br bridge, leaving the N-bonding intact. Therefore, three different reaction pathways have been characterized. The reactivity of the Pd-C bond in 7 has also been examined, and functionalized oxazolones can be obtained. The reaction of 7 With PhI(OAc)(2) in acetic acid gives the starting oxazolone C6H4-2-Br-CH=CNC(O)OCPh (4), through the presumed oxidation of the Pd center and C-Br bond formation by reductive coupling. In contrast, the reaction of the acetate dimer 14 with PhI(OAc)(2) in acetic acid gives C6H4-2-OAc-CH=CNC(O)OCPh (20) through C-O coupling. When treatment of 7 with PhI(OAc)(2) is performed in MeOH or EtOH, the oxazolones C6H4-2-OR-CH=CNC(O)OCPh (R = Me (18), Et (19)) are obtained. The reaction of 7 with CO in alcohols ROH gives cleanly the oxazolones C6H4-2-CO2R-CH=CNC(O)OCPh (R = Me (21), Pr-i (22)) through CO migratory insertion into the Pd-C bond and further nucleophilic attack of the RO- fragment.