Pd(3-[N-2-pyridylmethyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino]ethylindole(1-)-κC2)Cl | 723242-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Pd(3-[N-2-pyridylmethyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino]ethylindole(1-)-κC2)Cl
• 英文别名: [Pd(3-(N-2-pyridylmethyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino)ethylindole(-1H))Cl]；2,4-ditert-butyl-6-[[2-(1,2-dihydroindol-2-id-3-yl)ethyl-(pyridin-2-ylmethyl)amino]methyl]phenol;palladium(2+);chloride
• CAS: 723242-25-9
• 化学式: C₃₁H₃₈ClN₃OPd
• 分子量: 610.535
• InChiKey: PIPUHHFMWJNPBZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  48.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Pd(3-[N-2-pyridylmethyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino]ethylindole(1-)-κC2)Cl 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Pd–C bond formation with the indole ring in palladium complexes of N,N,O-donor ligands. Effect of the nitrogen donor properties

  摘要：

  The Pd(II) complexes of three new N,N,O-donor ligands with a pendent indole ring and participation of the indole ring in Pd(II) binding have been studied by synthetic, structural, and kinetic methods. The reactions of ligands, 2-[N-2-(1-methylimidazolyl)methyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino]ethyl-3-indole (Hieip), 2-[N-2-(1,4,5-trimethylimidazolyl) methyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino] ethyl-3-indole (HMe3-ieip) and 2-[N-2-(6-methypyridyl)-methyl-N-2-hydroxy-3,5-di(tert-butyl) benzylamino]ethyl-3-indole (HMe-iepp), with [PdCl2(CH3CN)(2)] at room temperature gave the complexes [Pd(ieip)Cl], [Pd(Me-3-ieip)Cl] and [Pd(Me-iepp)Cl], respectively, as reddish-brown crystals. The X-ray crystal structure analyses and H-1 NMR spectra revealed that all the complexes have a phenolate coordination in a square-planar geometry and that the pendent indole ring has no characteristic intramolecular interaction with the Pd(II) ion and the coordinated pyridine and imidazole moieties. The distortion of the coordination plane is in the order [Pd(ieip)Cl] < [Pd(Me-3-ieip)Cl] < [Pd(Me-iepp)Cl]. Heating a solution of each of the phenolate complexes gave yellow crystals, which were shown to be the indole-C2 binding complex by X-ray analysis. The Pd(II)-O(phenolate) to Pd(II)-C(indole) conversion characteristics of these complexes depends on the nitrogen donor properties of the trans position of the coordinated indole moiety, and the order of the conversion rate of Pd-indole binding complexes is in good correlation with the coordination plane distortion. On the basis of kinetic studies, the influence of the aromatic nitrogen donors to form the indole-C2 binding complexes and the detailed mechanism of the conversion were discussed. Crown Copyright (c) 2013 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.07.032
• 作为产物：
  描述：

  3-[N-2-pyridymethyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino]ethylindole 在 triethylamine 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Pd(3-[N-2-pyridylmethyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino]ethylindole(1-)-κC2)Cl
  参考文献：
  名称：

  2N1O-供体配体的钯(II)配合物中吲哚环的反应性：环钯化和π-阳离子自由基形成

  摘要：

  包含悬垂吲哚、3-[N-2-吡啶甲基-N-2-羟基-3,5-二(叔丁基)苄氨基]乙基吲哚 (Htbu-iepp) 的新型 2N1O 供体配体的 Pd(II) 配合物, 1-methyl-3-[N-2-pyridylmethyl-N-2-hydroxy-3,5-di(tert-butyl)benzylamino]ethylindole (Htbu-miepp), 3-[N-2-pyridylmethyl-N- 2-羟基-3,5-二（叔丁基）苄氨基]甲基吲哚（Htbu-impp）和3-（N-2-吡啶甲基-N-4-羟基苄氨基）乙基吲哚（Hp-iepp）（H表示可解离的质子），合成 [Pd(tbu-iepp)Cl] (1a)、[Pd(tbu-iepp-c)Cl] (1b)、[Pd(tbu-miepp)Cl] (3) 的结构和 [Pd(p-iepp-c)Cl] (4)（tbu-iepp-c 和 p-iepp-c

  DOI：

  10.1021/ja031587v

文献信息

• Cyclopalladation of the Indole Ring in Palladium(II) Complexes of 2N1O-Donor Ligands and Its Dependence on the O-Donor Properties
  作者：Yuichi Shimazaki、Minoru Tashiro、Takeshi Motoyama、Satoshi Iwatsuki、Tatsuo Yajima、Yasuo Nakabayashi、Yoshinori Naruta、Osamu Yamauchi

  DOI：10.1021/ic0504801

  日期：2005.8.1

  [Pd(iepc)Cl] (4) were prepared and revealed by X-ray analysis to have a pyridine nitrogen, an amine nitrogen, a phenolate or carboxylate oxygen, and a chloride ion in the coordination plane. UV absorption and 1H NMR spectral changes indicated that all the complexes could be converted to the indole-binding complexes where the O donor was replaced by the indole C2 atom by cyclopalladation in DMSO or DMF

  已对新型2N1O供体配体的Pd（II）配合物进行了合成，结构，光谱和动力学研究，这些配体包含悬垂的吲哚3-（N-2-吡啶基甲基-N-2-羟基-5-甲氧基苄基氨基）乙基吲哚（HMeO-iepp），3-（N-2-吡啶基甲基-N-2-羟基-5-硝基苄氨基）乙基吲哚（HNO2-iepp）和（N-2-吡啶基甲基-3-吲哚基乙基氨基）乙酸（Hiepc） （H表示可解离的质子）。制备[Pd（MeO-iepp）Cl]（2），[Pd（NO2-iepp）Cl]（3）和[Pd（iepc）Cl]（4），并通过X射线分析显示有吡啶配位平面中的氮，胺氮，酚或羧酸氧和氯离子。紫外吸收和1H NMR光谱变化表明，所有配合物均可转化为吲哚结合配合物，其中O供体在40-60℃的温度范围内在DMSO或DMF中通过环钯反应被吲哚C2原子取代。吲哚结合的复杂物种中的一部分服从一级动力学，由此估计活化参数。形成速率取决于O-给体基团