2,5-bis(3-(tert-butyl)-2-methoxyphenyl)-1H-pyrrole | 1480402-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-bis(3-(tert-butyl)-2-methoxyphenyl)-1H-pyrrole
• 英文别名: 2,5-bis(3-tert-butyl-2-methoxyphenyl)-1H-pyrrole
• CAS: 1480402-87-6
• 化学式: C₂₆H₃₃NO₂
• 分子量: 391.554
• InChiKey: UVNJOSJTBRLFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-bis(3-(tert-butyl)-2-methoxyphenyl)-1H-pyrrole 在 potassium tert-butylate 、 2-甲胺乙硫醇盐酸盐 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以36%的产率得到6,6'-(1H-pyrrole-2,5-diyl)bis(2-(tert-butyl)phenol)
  参考文献：
  名称：

  Synthesis and Characterization of Tungsten Alkylidene and Alkylidyne Complexes Supported by a New Pyrrolide-Centered Trianionic ONO^3– Pincer-Type Ligand

  摘要：

  Synthetic protocols for a pyrrolide-centered ONO3- trianionic pincer-type ligand are presented. Treating ((BuO)-Bu-t)(3)W equivalent to(CBu)-Bu-t with the proligand [pyr-ONO]H-3 (2) results in the formation of the trianionic pincer alkylidene complex [pyr-ONO]W=(CHBu)-Bu-t((OBu)-Bu-t) (3). Addition of a mild base to complex 3 provides the trianionic pincer alkylidyne complex {MePPh3}{[pyr-ONO]W equivalent to(CBu)-Bu-t((OBu)-Bu-t)} (4). All new compounds were characterized by NMR spectroscopy, combustion analysis, and, in the case of complex 4, single-crystal X-ray crystallography. D FT calculations performed on 4 provide insight into its electronic structure and indicate that the HOMO is ligand-based and localized on the pyrrolide pi orbitals.

  DOI：

  10.1021/om4009422
• 作为产物：
  描述：

  (3-(tert-butyl)-2-methoxyphenyl)boronic acid 在 盐酸 、 四(三苯基膦)钯 、 potassium chloride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 反应 38.0h， 生成 2,5-bis(3-(tert-butyl)-2-methoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  Synthesis and Characterization of Tungsten Alkylidene and Alkylidyne Complexes Supported by a New Pyrrolide-Centered Trianionic ONO^3– Pincer-Type Ligand

  摘要：

  Synthetic protocols for a pyrrolide-centered ONO3- trianionic pincer-type ligand are presented. Treating ((BuO)-Bu-t)(3)W equivalent to(CBu)-Bu-t with the proligand [pyr-ONO]H-3 (2) results in the formation of the trianionic pincer alkylidene complex [pyr-ONO]W=(CHBu)-Bu-t((OBu)-Bu-t) (3). Addition of a mild base to complex 3 provides the trianionic pincer alkylidyne complex {MePPh3}{[pyr-ONO]W equivalent to(CBu)-Bu-t((OBu)-Bu-t)} (4). All new compounds were characterized by NMR spectroscopy, combustion analysis, and, in the case of complex 4, single-crystal X-ray crystallography. D FT calculations performed on 4 provide insight into its electronic structure and indicate that the HOMO is ligand-based and localized on the pyrrolide pi orbitals.

  DOI：

  10.1021/om4009422
• 作为试剂：
  描述：

  (3-(tert-butyl)-2-methoxyphenyl)boronic acid 、 disodium;carbonate 、 氯化钾 、 2,5-二溴-1H-吡咯-1-羧酸-1,1-二甲基乙酯 、 、 吡咯 、 甲苯 在 四(三苯基膦)钯 氩 、 二氯甲烷 、 水 、 Brine 、 magnesium sulfate 、 hexanes 、 BOC 、 盐酸 、 1,4-二氧六环 、 CH2Cl 、 disodium;carbonate 、 异丙醇 、 2,5-bis(3-(tert-butyl)-2-methoxyphenyl)-1H-pyrrole 作用下， 以 water ethanol 为溶剂， 反应 38.5h， 生成 2,5-bis(3-(tert-butyl)-2-methoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  ONO PINCER LIGANDS AND ONO PINCER LIGAND COMPRISING METAL COMPLEXES

  摘要：

  本发明的实施例涉及可以处于三阴离子、质子化或质子化等效形式的ONO夹持配体。ONO夹持配体可以与含有过渡金属的化合物结合，形成含有过渡金属的ONO夹持配体配合物。通过选择ONO夹持配体结构，可以控制过渡金属配合物的立体和电子性质。ONO夹持配体包括一个中心氮原子，该中心氮原子被一对三原子桥连接，其中三个原子是三个sp2杂化碳或一对sp2杂化碳和一个sp3杂化碳或硅原子。

  公开号：

  US20140073800A1

文献信息

• ONO Pincer Ligands and ONO Pincer Ligand Comprising Metal Complexes
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20170022230A1

  公开（公告）日：2017-01-26

  Embodiments of the invention are directed to ONO pincer ligands that can be in a trianionic, protonated or protonated equivalent form. The ONO pincer ligand can be combined with a metal comprising compound to form an ONO pincer ligand comprising transition metal complex. By choice of the ONO pincer ligand structure, the steric and electronic properties of the metal complexes therefrom can be controlled. The ONO pincer ligands comprise a central nitrogen atom that is disubstituted with a pair of three atom comprising bridges where the three atoms are a pair of sp 2 hybridized carbons and an sp 3 hybridized carbon.
• US9464104B2
  申请人：——

  公开号：US9464104B2

  公开（公告）日：2016-10-11
• US9765102B2
  申请人：——

  公开号：US9765102B2

  公开（公告）日：2017-09-19
• Synthesis and Characterization of Tungsten Alkylidene and Alkylidyne Complexes Supported by a New Pyrrolide-Centered Trianionic ONO^3– Pincer-Type Ligand
  作者：Matthew E. O’Reilly、Soufiane S. Nadif、Ion Ghiviriga、Khalil A. Abboud、Adam S. Veige

  DOI：10.1021/om4009422

  日期：2014.2.24

  Synthetic protocols for a pyrrolide-centered ONO3- trianionic pincer-type ligand are presented. Treating ((BuO)-Bu-t)(3)W equivalent to(CBu)-Bu-t with the proligand [pyr-ONO]H-3 (2) results in the formation of the trianionic pincer alkylidene complex [pyr-ONO]W=(CHBu)-Bu-t((OBu)-Bu-t) (3). Addition of a mild base to complex 3 provides the trianionic pincer alkylidyne complex MePPh3}[pyr-ONO]W equivalent to(CBu)-Bu-t((OBu)-Bu-t)} (4). All new compounds were characterized by NMR spectroscopy, combustion analysis, and, in the case of complex 4, single-crystal X-ray crystallography. D FT calculations performed on 4 provide insight into its electronic structure and indicate that the HOMO is ligand-based and localized on the pyrrolide pi orbitals.
• ONO PINCER LIGANDS AND ONO PINCER LIGAND COMPRISING METAL COMPLEXES
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：US20140073800A1

  公开（公告）日：2014-03-13

  Embodiments of the invention are directed to ONO pincer ligands that can be in a trianionic, protonated or protonated equivalent form. The ONO pincer ligand can be combined with a transition metal comprising compound to form an ONO pincer ligand comprising transition metal complex. By choice of the ONO pincer ligand structure, the steric and electronic properties of the transition metal complexes therefrom can be controlled. The ONO pincer ligands comprise a central nitrogen atom that is disubstituted with a pair of three atom comprising bridges where the three atoms are three sp 2 hybridized carbons or the three atoms are a pair of sp 2 hybridized carbons and an sp 3 hybridized carbon or silicon.

  本发明的实施例涉及可以处于三阴离子、质子化或质子化等效形式的ONO夹持配体。ONO夹持配体可以与含有过渡金属的化合物结合，形成含有过渡金属的ONO夹持配体配合物。通过选择ONO夹持配体结构，可以控制过渡金属配合物的立体和电子性质。ONO夹持配体包括一个中心氮原子，该中心氮原子被一对三原子桥连接，其中三个原子是三个sp2杂化碳或一对sp2杂化碳和一个sp3杂化碳或硅原子。