1,3-bis(anthracen-9-yl)-imidazolinium tetrafluoroborate | 1025031-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-bis(anthracen-9-yl)-imidazolinium tetrafluoroborate
• 英文别名: 1,3-bis(anthracen-9-yl)-imidazolinium tetrafluoroborate
• CAS: 1025031-06-4
• 化学式: BF₄*C₃₁H₂₃N₂
• 分子量: 510.342
• InChiKey: ZUHFOXVHTYCWIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.79
• 重原子数：
  38.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  6.25
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(anthracen-9-yl)-imidazolinium tetrafluoroborate 在 potassium tert-butylate sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以90%的产率得到1,3-bis(anthracen-9-yl)-imidazolidene
  参考文献：
  名称：

  Identification and Characterization of a New Family of Catalytically Highly Active Imidazolin-2-ylidenes

  摘要：

  A new class of easily accessible and stable imidazolin-2-ylidenes has been synthesized where the side chains are comprised of substituted naphthyl units. Introduction of the naphthyl groups generates C-2-symmetric (rac) and C-s-symmetric (meso) atropisomers, and interconversion between the isomers is studied in detail both experimentally and computationally. Complete characterization of the carbenes includes rare examples of crystallographically characterized saturated NHC structures. Steric properties of the ligands and an investigation of their stability are also presented. In catalysis, the new ligands show versatility comparable to the most widely used NHCs IMes/SIMes or IPr/SIPr. Excellent catalytic results are obtained when either the NHC salts (ring-opening alkylation of epoxides), NHC-modified palladium compounds (C-C and C-N cross-couplings), or NHC-ruthenium complexes (ring-closing metathesis, RCM) are employed. In several cases, this new ligand family provides catalytic systems of higher reactivity than that observed with previously reported NHC compounds.

  DOI：

  10.1021/ja800861p
• 作为产物：
  描述：

  N,N'-bis(anthracen-9-yl)ethane-1,2-diamine 、 原甲酸三乙酯 在 甲酸 ammonium tetrafluoroborate 作用下， 反应 2.0h， 以71%的产率得到1,3-bis(anthracen-9-yl)-imidazolinium tetrafluoroborate
  参考文献：
  名称：

  Identification and Characterization of a New Family of Catalytically Highly Active Imidazolin-2-ylidenes

  摘要：

  A new class of easily accessible and stable imidazolin-2-ylidenes has been synthesized where the side chains are comprised of substituted naphthyl units. Introduction of the naphthyl groups generates C-2-symmetric (rac) and C-s-symmetric (meso) atropisomers, and interconversion between the isomers is studied in detail both experimentally and computationally. Complete characterization of the carbenes includes rare examples of crystallographically characterized saturated NHC structures. Steric properties of the ligands and an investigation of their stability are also presented. In catalysis, the new ligands show versatility comparable to the most widely used NHCs IMes/SIMes or IPr/SIPr. Excellent catalytic results are obtained when either the NHC salts (ring-opening alkylation of epoxides), NHC-modified palladium compounds (C-C and C-N cross-couplings), or NHC-ruthenium complexes (ring-closing metathesis, RCM) are employed. In several cases, this new ligand family provides catalytic systems of higher reactivity than that observed with previously reported NHC compounds.

  DOI：

  10.1021/ja800861p