| 1400813-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• CAS: 1400813-14-0
• 化学式: C₂₁H₁₄O₂
• 分子量: 298.341
• InChiKey: VJYCJXWNCMMMQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  22.37
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  在 Ag[1-closo-CB11H6Cl6] 、 [PtCl₃(P(C₃(NMe₂)2)3)](perchlorate)2 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 、 18-Methoxy-3-oxapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-1(13),2(10),4,6,8,11,14,16(21),17,19-decaene
  参考文献：
  名称：

  Exploiting the π-Acceptor Properties of Carbene-Stabilized Phosphorus Centered Trications [L₃P] ³⁺: Applications in Pt(II) Catalysis

  摘要：

  Reaction of tris(dimethylaminocyclopropenium) substituted phosphine 1 with K2PtCl4 afforded the bench stable complex 3 which upon treatment with Ag[CB11H6Cl6] turned out to be an excellent catalyst for the transformation of a variety of ortho-biaryl substituted alkynes into polycyclic homo- and heteroarenes of different size, shape, and curvature through a 6-endo-dig cyclization. This constitutes the first example ever reported of using a P-1-centered trication as ligand in catalysis. The strong pi-acceptor character of 1 that derives from its three positive charges substantially increases the intrinsic pi-acidity of Pt in complex 1.PtCl2 and dramatically enhances its ability to activate pi-systems toward nucleophilic attack. As a consequence, a remarkable acceleration of the model transformation is observed when compared with other classical pi-acceptor ligands such as P(OPh)(3) or P(C6F5)(3). Moreover, the employment of 1 as ligand also expands the scope of this reaction to previously inaccessible substitution patterns. Kinetic studies and deuterium labeling experiments as well as density functional theory (DFT) calculations were performed in order to explain these findings.

  DOI：

  10.1021/ja306947m
• 作为产物：
  描述：

  4-二苯并呋喃硼酸 在 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Exploiting the π-Acceptor Properties of Carbene-Stabilized Phosphorus Centered Trications [L₃P] ³⁺: Applications in Pt(II) Catalysis

  摘要：

  Reaction of tris(dimethylaminocyclopropenium) substituted phosphine 1 with K2PtCl4 afforded the bench stable complex 3 which upon treatment with Ag[CB11H6Cl6] turned out to be an excellent catalyst for the transformation of a variety of ortho-biaryl substituted alkynes into polycyclic homo- and heteroarenes of different size, shape, and curvature through a 6-endo-dig cyclization. This constitutes the first example ever reported of using a P-1-centered trication as ligand in catalysis. The strong pi-acceptor character of 1 that derives from its three positive charges substantially increases the intrinsic pi-acidity of Pt in complex 1.PtCl2 and dramatically enhances its ability to activate pi-systems toward nucleophilic attack. As a consequence, a remarkable acceleration of the model transformation is observed when compared with other classical pi-acceptor ligands such as P(OPh)(3) or P(C6F5)(3). Moreover, the employment of 1 as ligand also expands the scope of this reaction to previously inaccessible substitution patterns. Kinetic studies and deuterium labeling experiments as well as density functional theory (DFT) calculations were performed in order to explain these findings.

  DOI：

  10.1021/ja306947m